best road trips through new england

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Home » North America » USA » New England

EPIC New England Road Trip Itineraries (2024)

Going on a New England road trip  has to be one of the best ways to experience the region! With your own vehicle, you’ll be able to go wherever you want, stay where you like, and see whatever you fancy.

New England has been charming visitors for a long time. Of all of the regions in the USA, New England has some the richest history (being the birthplace of the nation and all), some of the most exciting locals, and best seafood, period.

And the fall foliage in New England? What more can be said about this phenomenon that hasn’t be said by dozens of movies – it’s simply one of the most romantic sights in the USA.

New England is by no means cheap nor easy to travel without some guidance. In order to see the best of New England, and not drop a fortune while doing so, you’re going to need a little assistance.

Don’t worry – we have the insider information you need for an EPIC journey. So what are we waiting for?! Let’s get the ball rolling on your New England road trip itinerary!

Best Time of Year to Road Trip New England

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With something always going on, a road trip to New England is possible at any time of the year! In New England, summers are for beach trips, fall is for the foliage, winter is for skiing, and spring is for festivals.

If you can stand the occasional poor weather – the blinding snow and sometimes uncomfortable humidity – then you’ll do just fine in New England.

The climate in New England isn’t always agreeable, a fact that many residents will remind you of when you’re there. Winters are long and can be bitter cold and summers feel unfairly humid and short.

The weather in New England has a habit of being bipolar as well, appearing beautiful one moment only to turn to shit in a moment.

This doesn’t stop New Englanders from having a good time though as they seem to have something to do 365 days of the year. They take the weather with a grain of salt, as they should, and simply say, “if the weather’s no good, just wait 15 minutes (and it’ll be better).”

Outside of the mountainous regions, which can have Arctic qualities, there are no huge climatic swings in New England. Overall, temperatures are relatively cool and precipitation is spread throughout the year.

What makes New England feel so cold is the Canadian winds that come down and wreak havoc. These winds penetrate to the bone and can really ruin your day.

A thermometer may read 30 Fahrenheit but with the wind chill, it could feel like 0. Be sure to bring lots of layers and a windbreaker in the winter.

Fall in New England means changing foliage, the astounding beauty of which attracts every Joe Schmoe and his family to visit. If you’re on a road trip during this time, expect much higher prices and much less availability. Having said that, it’s one of the best places in the world to visit in September and October, so it’s worth it!

Get 15% OFF when you book through our link — and support the site you love so dearly 😉

Booking.com is quickly becoming our go-to for accommodation. From cheap hostels to stylish homestays and nice hotels, they’ve got it all!

Below is a list of sample New England road trip routes, from East Coast budget adventures to more comprehensive trips that cost a bit more. Varying from 4 to 14 days in length, they cover many of the top destinations in New England. Each itinerary provides day-by-day highlights, which are meant to give you some good New England road trip ideas.

The USA is  blisteringly beautiful. It’s also blisteringly expensive! Visiting two national parks in day can run you $70+ in entry fees.

Orrrr… you kick those entry fees to the curb, buy an annual ‘America the Beautiful Pass’ for $79.99,  and get unlimited access to ALL 2000+ federally managed sites in the States totally FREE!

You do the math. 😉

4-Day New England Road Trip Itinerary: Boston and the Cape

4 Days: Boston and the Cape

Arrive in Boston via Logan International Airport or by other means. Once you’re checked into your lodge and settled in, get ready to see the town!

Our  Boston itinerary  includes a visit to downtown Boston to see:

• Fenway Park
• The Freedom Trail
• Acorn Street
• Trinity Church
• Boston Commons

After that, head to bed because the next day we start again!

Today you’ll be getting off the beaten path in Boston.

• Southend for an authentic Bostonian experience
• Cambridge for Harvard and MIT
• East Boston for good food and views
• Walden Pond for transcendental fans
• Bunker Hill for history

Today we’re officially starting the drive, so have your car organized for a road trip to Cape Cod. Start driving on Highway 6 and then transfer to Highway 3 prior to the Cape Cod Canal. Once you’ve arrived, find your Cape Cod lodge/campsite and get set up.

Next, we’ll explore the Cape. Activities include:

• Lighthouses
• Charming settlements
• Trinket shopping
• Historical landmarks
• Biking and hiking
• Cape Cod Rail Trail

This is the last day of your short road trip from Boston. You can opt for a few different choices today.

Either consider visiting Nantucket Island or Martha’s Vineyard via the ferry. If not though, you can continue exploring the island and seeing what’s around.

When all is said and done, pack your things for a late flight in the evening or a flight the next day.

7 Day New England Road Trip Itinerary: New England’s Best Fall Foliage

7 Days: New England’s Best Fall Foliage

• Arrive at Logan International and organize your car; skip this if you’re coming by road from elsewhere.
• Hit the road immediately and head west on the I-90 and I-84 for Hartford, CT.
• Pass Hartford and continue onto the Litchfield Hills in West Connecticut.
• Spend the night in Kent, Cromwell or elsewhere.
• Admire the foliage.
• Depart from your lodge and head north on I-7 through the Housatonic Valley; red and gold foliage in abundance.
• Arrive at the junction between I-7 and Highway 2 near Williamstown.
• Highway 2 is colloquially referred to the Mohawk Trail, which offers some of the best of New England as well as excellent fall colors.
• Stay nearby and drive along the 2 to your heart’s desire.
• Drive on the Mohawk Trail if you haven’t already.
• When ready, head for Green Mountain National Forest of Vermont via I-7 again.
• Drive through the Green Mountains until Burlington.
• Grab a beer and chill for the night.

Today is a long but rewarding day.

• Depart from Burlington and head for Cambridge, VT.
• Hit the 108 and Smuggler’s Notch for excellent mountain views and foliage.
• Make your way east towards Bath, New Hampshire.
• Turn onto Highway 112 before Bath, which is the beginning of the Kancamagus Highway.
• Continue onto Lincoln, admiring the scenery along the way.
• Stay in Lincoln, North Conway or elsewhere in the White Mountains.
• Finish the Kancamagus Highway (112), which terminates at Conway.
• Head north upon reaching Conway on Highway 16.
• Enjoy Mt Washington and White Mountain National Forest, which is particularly fantastic in fall.
• Turn onto I-2 and then again onto 113 to reach Evans Notch.
• Finish up and head south towards Portland for the night.
• Drive to Acadia National Park , which is one of the best places for fall foliage in New England.
• Make a tour around Mt Desert Island and get a full dose of autumn splendor and coastline.
• Spend the night around Acadia or back in Portland.
• Consider spending the night in Camden as there is excellent foliage here.
• Pack up and head back to Boston.
• Spend the day exploring the city.
• Get ready to depart that evening or the next day.

14-Day New England Road Trip Itinerary: Ultimate New England

14 Days: Ultimate New England Road Trip

Follow the first East Coast itinerary listed here  except  instead of returning to Boston at the end of day 4, relax and stay the night in Cape Cod. We’ll be moving on from there the next day…

• Depart from Cape Cod and hit I-6, which will take you all the way to Providence, Rhode Island.
• Explore the city and its architecture.
• Be sure to drop by one of the many breweries and brewpubs.
• Spend the night in or around Providence.
• Wake up and head directly for Newport via Highway 114.
• Spend the day exploring the opulent town.
• Be sure to visit the many mansions and estates as well as Fort Adams in the south.
• Depart when you’re ready.
• Drop by Narragansett for some beach time if you have time.
• Stop in Old Saybrook for the night or continue onto New Haven.
• Depart from your lodge and make your way north.
• Head to the state capital Hartford.
• Wadsworth Falls
• Buttermilk Falls
• Settle in Hartford for some culture and good partying or…
• Head to Litchfield Hills for a quieter night.
• Make your way up Knowledge Corridor or Housatonic Valley towards Vermont.
• Be sure to drop by the Mohawk Trail in Northwest Massachusetts for some scenery and history.
• Hit highway 7 and make the long drive to Burlington.
• Reward your hard work today with a beer.
• Spend the day exploring the Green Mountains of Vermont.
• Climbing the  Camel’s Hump .
• Hiking around  Mt Mansfield .
• Check out  Smuggler’s Notch .
• Rafting on the  Mad River .
• Spend the night in Burlington again.
• Depart from Burlington and head east towards Lincoln, New Hampshire via I-89.
• Arrive in the White Mountains and settle into whatever lodge/campground you have booked.
• Spend the remainder of the day in the mountains.
• Flume Gorge
• Mt Washington
• Franconia Notch
• Arethusa Falls
• Lonesome Lake
• If you arrived early enough, considering overnighting in a backcountry campsite.
• Wake up and knock off any remaining activities.
• Consider doing the full-day Presidential Traverse but, full-warning, it’s quite arduous.
• Lay your head down for the night, preferably around a campfire with a drink.
• Depart from the White Mountains and travel on Highway 302 to Portland, Maine.
• If you stay in Portland, visit the many maritime landmarks, trinket shops, and breweries.
• Spend the day exploring Acadia National Park.
• Taking a road trip around  Mt Desert Island .
• Climbing  Cadillac Mountain .
• Visiting  Jordan Pond .
• Relaxing on  Sand Beach .
• Walking around  Bar Harbor .
• Head to your lodge for the night.

Below is a list of the best road trip destinations in New England. Study them well and decide which ones you like the most.

Road Trip to Boston

Boston is the largest city in New England and, honestly, one of the coolest cities in the entire United States. With gorgeous architecture, some of America’s most important history, and hugely diverse demographics, there’s little chance you’ll run out of things to do in Boston .

Downtown Boston – the area with all the skyscrapers – is where you’ll find the majority of the city’s attractions. Notable points of interest in Boston Downtown include Fenway Park , the Trinity Church, Boston Commons, Acorn Hill , and the North End. You could easily hit all of these places in a few hours by walking.

North across the Charles River is Cambridge , home to the famously exclusive Harvard College and MIT . Both campuses are worth visiting – the former for traditional architecture and the latter for ultra-modern. The whole of Cambridge is pretty affluent, being inhabited by students and leaders in tech, but thankfully doesn’t suffer from too much snootiness.

South Boston is the home of the “southies” aka those people that sound like Matt Damon from Good Will Hunting . Aside from the impressive JFK Library, there isn’t a whole lot to do here besides people watch, which is, admittedly, awesome.

Finally, across the Boston Channel and next to Logan International is East Boston, which is where most of the immigrants live. These means this is one of the best places in Boston to grab food! The views ain’t bad either.

While you’re travelling around Boston , be sure to also get outside of the city of as well! The historical city of Concord , as well as the hallowed Walden Pond , are both worth a day trip.

Road Trip to Cape Cod and the Islands

Cape Cod is a large, prominent peninsula located south of Boston. It is an immensely popular getaway destination due in part to its extensive coastline and profuseness of quaint coastal towns.

Combined with the ever-enchanting Martha’s Vineyard and Nantucket Island , both located nearby, and you have an assembly of some of the best of New England.

Cape Cod is a very large region, surprisingly so, and is broken into several districts. Because of its size, history, and prosperity, Cape Codians are very proud of their home and consider it more than just a tourist destination. There are loads of great places to stay in Cape Cod , if you fancy extending your trip!

There are several charming towns on Cape Cod that are worth visiting. Hyannis is most notable for the Kennedy Compound , which served as the holiday home for JFK and his family, as well the enormous Beech Tree on Main Street .

Fans of Kurt Vonnegut may also be interested in nearby Barnstable as it was his home for several decades. Affluent Chatham has one of the best lighthouses and local baseball teams on the Cape (Cape Codians are crazy for the sport).

Finally, Provincetown is famous for its artsy and expressive LGBT community.

Most everyone comes to Cape Cod to play in the sea as the peninsula has some of the best beaches in New England. Make no mistake, there are a lot of them too.

Stunning stretches of sand can be found at Nauset Beach, Lighthouse Beach, Sandy Neck Beach, Mayflower Beach, and pretty anywhere else along the Cape Cod National Shoreline Park . You may get lucky and even see a migrating humpback whale!

No road trip to Cape Cod is complete without a trip to Nantucket Island or Martha’s Vineyard – both are among the most desirable places to visit in New England, during summer especially so.

Martha’s Vineyard is full of grand residences for the rich as well as picturesque beaches. Nantucket is similar to Martha’s Vineyard but smaller and quieter. You can catch a ferry to either at Hyannis.

Road Trip to Rhode Island

Rhode Island has a little bit of everything. The largest city, Providence , is often considered a good alternative to Boston, and the surrounding state offers quintessential scenery including rugged coastline, quaint townships, and, of course, the fall foliage New England is so beloved for.

Providence is the third largest city in New England. For a long time, Providence had a bad reputation for being sketchy, crime-ridden, and corrupt but, following massive economic pushes, is currently undergoing an urban renaissance. It’s now a very appealing city thanks to its history with a bustling college scene, solid nightlife, and heaps of stuff to do .

Providence is a small city so getting around on a foot is a very reasonable task. Walk around and take note of the diverse architecture. Be sure to see the State House, the eclectic Brown University, the restored Arcade, and the First Baptist Church , among others, for a lesson in American architectural history.

For a languid afternoon, try visiting one of the many museums and/or parks in Providence. Certain neighborhoods, like Federal Hill, College Hill, and Downcity all offer nice urban panoramas as well. End your day at one of the many breweries in the city.

Rhode Island’s other noteworthy city is Newport . An opulent town, full of mansions and elegant avenues, Newport is a prime example of New England decadence. Rosecliff estate served as a setting in the recent Great Gatsby film and its neighbors – The Beakers and Marble House – are equally grandiose.

There is a thriving art scene in Newport and jazz, in particular, is praised here. There is an awesome jazz festival at Fort Adams. Festival or not, Fort Adams is worth seeing because it is one of the most important historical structures in New England.

Newport has many beautiful city beaches including Bailey’s, Easton, and Gooseberry. To see some real contenders for “best beaches in New England,” head across the Jamestown Verrazano Bridge to Narragansett . If you’re ever wondering where to stay in Newport, you should definitely consider staying in one of the more historic bed and breakfasts in Rhode Island there.

Coastal Connecticut Road Trip

Connecticut is an eclectic state visited often by both New Englanders and New Yorkers, the latter of which only live a short train ride away. It is a popular getaway for city folk who need a break from the grind and some time in rural New England.

With a lovely coastline, romantic countryside, and a number of dynamic cities, Connecticut is a great stop along any New England road trip route USA.

Connecticut can be broken down roughly into three parts: the coast, the “Knowledge Corridor,” and the countryside. This section will cover coastal Connecticut , which is a part of Southern New England.

Driving west along Highway 95 from Rhode Island, you’ll pass by some of the most beautiful beach towns in New England. Stonington is a good place to learn about the maritime history of the state – particularly at the Old Lighthouse Museum .

Old Saybrook is one of the prettiest coastal towns in Connecticut and is also a stone’s throw away from Gillette Castle . On the way to New Haven is Hammonasset Beach , which is the longest and busiest beach in the state. Make sure to stay in one of the stunning cabins in Connecticut to make the most out of all this natural scenery.

New Haven marks the beginning of a long stretch of urban development that spans all the way to New York state.

New Haven is most famous for Yale University , which is arguably the top attraction in the city. Being a college town, New Haven has a great art scene and nightlife. The pizza is also particularly good in this town.

As we continue further west along 95, we’ll pass by many more beautiful New England towns. There’s quiet Milford , which has a great beach called Silver Sands .

Next, you’ll pass through industrial Bridgeport . After that is upscale Stamford , glorified dockyard for millionaires from New York (there are some good beaches as well).

Finally, you’ll end up in Greenwich , which is one of the most admired towns in New England, due in part to its beauty and close proximity to New York.

There are a ton of awesome B&Bs in Connecticut where you can stay in a historical building and enjoy that welcoming East Coast hospitality.

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Road Trip through Connecticut and Massachusetts

The interior of Connecticut is dominated by the Knowledge Corridor , which hosts one of the densest collections of higher learning institutions, not to mention one of the largest populations in New England.

Travel outside this packed area and you’ll find some of some of the best of New England pastoralism including traditional townships, rolling hills, and a distinctive tranquility. Visiting either on a New England road trip provides excellent insight into the region.

Let’s start with the quieter section – the western part of Connecticut referred to as the Litchfield Hills. This part of the state is very rural with few inhabitants and even fewer visitors.

There are a number of beautiful New England towns here, including Kent , Cornwall , and New Milford , as well some lovely natural attractions like Kent Falls, Burr Pond, Candlewood Lake, and Mohawk Mountain . These are also some of the best places to visit in New England in the fall.

Moving along to our main destination, we first make for Hartford , Connecticut’s state capital and the beginning of the Knowledge Corridor. Hartford is considered one of the great culture capitals of the region.

There are several libraries and art collections dedicated to various historical figures, including Mark Twain, spread throughout the city. Reportedly, West Hartford also has a fairly active nightlife.

Outside of Hartford are a number of parks worth visiting. Examples include Enders State Forest/Falls, Buttermilk Falls , and Wadsworth Falls .

We continue our New England road trip north on Highway 91 through the Connecticut River Valley. This is the heart of the Knowledge Corridor, a title that refers to the huge concentration of colleges and universities in the area. This corridor runs all the way into Massachusetts and terminates in Springfield.

Springfield is a great city full of Victorian architecture and some of the coolest museums in New England. Be sure to visit the NBA Hall of Fame , if you’re interested in sports, as well as the Dr. Seuss Sculpture Museum , if you had a childhood.

Vermont Road Trip

True to its nickname, Vermont aka The Green Mountain State is a wild wonderland and a favorite playground for New England outdoors people. With some awesome skiing and hiking in addition to several fall foliage drives, which are among the best in New England, Vermont is a great escape from the more developed CT, MA, and RI. Here is the best opportunity to stay in a cabin in Vermont for a truly off-the-grid experience.

Starting in the south of Vermont, you’ll first arrive at the mountains from which the state gets its name, the Green Mountains . A subrange of the Appalachia, the Green Mountains are home to the state’s highest peaks as well as the best mountain activities.

Some of the best ski resorts in Vermont are Sugarbush, Stowe Mountain, Killington, Mount Snow , and Jay Peak. Though the slopes aren’t as epic as say those in Colorado or Oregon, they still get dumped on with snow and have decent runs.

If skiing isn’t your bag, why not try portions of the Green Mountain Long Trail ? This extension of the Appalachian Trail is noteworthy for hitting all the range’s highest peaks but is, for this reason, difficult at times.

Casual hikers and campers can also take advantage of the many free backcountry campsites and quaint bed and breakfasts in Vermont .

Other natural attractions worth visiting in Vermont are the Mad River, Quechee Gorge, Camel’s Hump , and the many gorgeous lakes – most notably Lake Willoughby and Lake Champlain.

Montpellier is the state capital of Vermont though Burlington is the largest and most exciting in the state.

Burlington is famous for being a hippy town as well as drop dead gorgeous because it lies on the banks of Lake Champlain. Burlington makes for an excellent base for exploring Vermont’s outdoor spaces with many quality bike paths for cycling enthusiasts.

Like any good liberal college town, Burlington has plenty of bars, and the breweries, in particular, are excellent. You ca check out Airbnbs in Vermont for cozy and comfortable stays.

Road Trip to New Hampshire

New Hampshire is very similar to Vermont in that it’s mostly visited for its epic settings and free-spirited culture. With the highest peak in all of New England, Mount Washington , as well as the beautiful White Mountains , New Hampshire is another great New England road trip destination for adventurous travelers.

If you’re on a summer New England road trip, then you’ll obviously want to hit the trails in New Hampshire. This state has some of the best hikes in New England in addition to some decent summits.

As previously mentioned, Mt Washington is the highest peak in New England and can be summitted in a day either by foot or by cog train (that’s cheating though). Be mindful of foul weather.

New Hampshire’s Mt Monadnock is argued to be the second most climbed peak in the world next to Mt Fuji, but many don’t count Monadnock because it has no glacier. (Mt Hood in Oregon is the second most climbed glaciated peak in the world.)

Another rewarding and arduous hike is the Presidential Traverse where you navigate across 11 of the state’s highest peaks. Also consider visiting Lake Winnipesaukee , Franconia Notch, Arethusa Falls, Lonesome Lake , and the Flume Gorge .

Those on a winter or spring New England road trip will be happy to hear the skiing is also quite good in New Hampshire. Popular ski resorts include Loon Mountain, Bretton Woods, Cannon Mountain , and Waterville Valley .

New Hampshire is pretty sparsely populated and there aren’t too many bustling urban centers here. There are a couple of little towns worth stopping in still.

Hanover is home to the famous Dartmouth University and is gorgeous in its own right. Jackson is a gorgeous place to stay in the White Mountains and makes for a great base. Finally, Portsmouth is one of the most historically significant towns in New England and, more importantly, has great breweries.

Road Trip on the Maine Coast

Maine will be a highlight for any New England Coast road trip! With epic seascapes and even more epic seafood, Maine has a lot to offer.

Many people have fallen in love with Maine’s coastline, too many perhaps. Coastal Maine isn’t exactly hidden these days and so anyone on a summer road trip in New England will have to deal with large crowds.

You can definitely get off the beaten path in Maine but that is a topic that we will be discussing in the next section .

Driving from Portsmouth, NH, you’ll head north on the 95 to Portland , Maine, catching glimpses of the shoreline along the way. You’ll pass by several of Maine’s best beaches and towns including York, Ogunquit, Cape Elizabeth , and Goose Rocks . Upon arriving in Portland, you may think that it’s a small coastal town but is, in fact, the largest “city” in the state.

Portland is one of the best places in New England, ridiculously charming and full of quaint little attractions. You’ll learn a lot about its maritime history at the Old Port and also be afforded the opportunity to shop for artisanal souvenirs. The seafood is obviously excellent in Portland and the beer is especially delicious if not abundant.

Moving on from Portland, we continue our New England coast road trip deeper into the state. Driving on the 1 you’ll have lots of opportunities to visit the coast. Boothbay is an elegant destination, Camden is gorgeous, and Popham Beach is arguably one of the best beaches in New England.

Our ultimate destination is Acadia National Park , the only national park in New England. It is a superlative place with some astounding scenery, not to mention some of the best hikes in New England.

Spend the night in the charming seaside town of Bar Harbour , where you’ll get to try Maine’s famous cold lobster roll. You’ll find some epic Maine B&Bs here run by friendly locals.

Then go for a drive around Mt Desert Island , the island on which Acadia is located, and then explore local sites like Jordan Pond and Sand Beach . Note that you’ll have to pay an entry fee for Acadia.

Below is an overview of the Great North Woods of New England, arguably the wildest place in the Northeast. Those with the will and proper transport will be rewarded with virgin woods, pristine rivers, and an abundance of local wildlife.

Great North Woods

The Great North Woods is one of the quietest, most underdeveloped, and most beautiful places in New England. It refers to the extremely wild and untouched woodlands of northern New Hampshire, Vermont, and Maine that separate New England from Canada.

With little, if any tourist infrastructure, the Great North Woods should be an awesome adventure for anyone looking for a proper USA backcountry experience on their New England road trip.

There are a fair bit of activities in the New Hampshire part of the Great North Woods. Many of New England’s best waterfalls are in this region including the spectacular Beaver Brook Falls . There’s a very complex and thorough network of trails here as well that penetrates deep into the woods.

You can drive to Great North Woods in Maine from New Hampshire via Highway 16 and pass some excellent scenery along the way. This area is one of the best places to visit in New England in the fall because of the spectacular foliage. Be careful of moose though! These giants will run into the road sometimes and seriously ruin your car.

Maine’s North Woods is expansive and is probably the most remote part of New England. It is, in fact, so out-there that certain counties like Aroostook are not even officially incorporated into the state and so have no “official populations.”

Stories of the wood’s frightful and fantastic inhabitants still circulate to this day as well, like that of the vengeful wendigo or of the murderous ding-balls.

Interior locations like Baxter State Park and Mt Katahdin are the most “accessible” places in Maine’s North Woods. Surrounding these is 100 Mile Wilderness , which is often visited by ACT hikers. If you want to travel further than these locations you may need a 4×4 as paved roads are no longer guaranteed.

If you can make it, the Allagash Wilderness is one of the great river adventures in America. Navigable only by canoe or raft, there is nothing out here besides moose, fish, and untouched landscapes.

A road trip through New England ain’t going to be cheap, folks. With the high costs of living and high demand, New England has some of the steepest hotel rates and dining prices in the USA.

That’s no reason not to visit New England in the first place though! You have us, after all. 🙂

We at The Broke Backpacker are constantly looking for new ways to save on travel and have a whole repertoire of useful tips to share with y’all. Even if we are unable to travel for $10/day like in our favorite countries (let’s be real here), we can at least help you minimize expenses to the utmost degree.

The average daily budget for a New England road trip is between $200-$250 – this includes gas, a rental car, lodging, food, drink, and entry fees.

On any road trip, New England or otherwise, the largest cost will be gas . This expense will always sneak up on you because it can be difficult to properly gauge how much you will actually use.

Lodging is also expensive in New England. Try and camp out as much as possible to lower your daily budget significantly. Take advantage of the cheaper public campsites and occasional backcountry site, which are sometimes free. Stay in hostels as well – they’re not so bad in New England.

Food costs are something you can control as you will have the option of cooking cheaply at home or the campsite. Dining is expensive in New England so be picky about how many lobsters you eat and clam bakes you attend.

Below is a breakdown of the average costs of a road trip in New England.

Average Costs of a New England Road Trip

Rental car : $50-$150

RV rental :  $100-$300

Gallon of gas:  $2.74

Private AirBnB home:  $140

Hotel room:  $150

Hostel:  $25-$35

Campground:  $10-30 (sometimes free!)

Sandwich:  $6-$9

Beer at a bar:  $5-$8

Coffee:  $3-$4

Bottle of Whiskey from the market:  $25

Dinner for two:  $35-$60

Best Places to Stay in New England on a Budget

Camping in new england.

Camping in New England is either done on public land, private land or in the backcountry . Each type offers different sorts of amenities and at different prices.

Private campgrounds usually have more amenities and can accommodate more types of campers. RV parks, hookup sites, and other sorts of demanding camping (we hesitate to use the word “glamping”) are usually found at private camps.

Private camps usually have lots of communal facilities like a kitchen and showers. Because of their greater comfort, private campgrounds are usually more expensive.

Camping on public land, run either by the state or the feds, is usually more basic. Electricity is possible as is the occasional shower but don’t expect the resort-like services that private campgrounds have. Fortunately, prices are far more reasonable at public campgrounds.

Both public and private campsites fill up quickly in the fall. Many take reservations though and we suggest you do this if you’re going on a fall foliage road trip in New England.

Backcountry campsites, being located on either private or public land, are harder to access but have the benefit of being extremely cheap if not totally free . These campgrounds usually require a hike or maybe a water taxi to reach, which makes them difficult and unattractive for the average camper.

The backcountry campgrounds are also very primitive, often with no restrooms and maybe running water. For the intrepid, these campgrounds can be very ideal as they’re super quiet, wild, and, as previously mentioned, usually free!

Backcountry campsites are usually found in the mountains, around the lakes, and on the remote islands of New England. Use this search engine for a compendium of free camping in New England .

Always have of plenty of powerful bug spray and mosquito repellent on you. Mosquitoes are a plague in the summer. Be sure to also wear long clothing to protect yourself from ticks when hiking in the backcountry. Local ticks often carry Lyme Disease, which is an autoimmune disorder with no cure.

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We’ve tested the Geopress  rigorously  from the icy heights of Pakistan to the tropical jungles of Bali, and can confirm: it’s the best water bottle you’ll ever buy!

Renting a Car or Campervan in New England

Renting a car is the most popular way of getting around New England. There are a myriad of car rental agencies here that offer varying deals and varying models.

To find the best rental car deal in the USA, use search engines that compare the prices from individual companies. We personally like using rentalcars.com as they’ve never failed to give us a great price.

You can also rent and travel in a campervan , which means you don’t have to worry about packing camping gear. You will have to empty and refill the various wascampete and water tanks though, which will require a visit to the proper facilities. RVs also cost more to rent, use more gas, and demand higher prices at campgrounds. We suggest booking a campervan with Outdoorsy as they usually have a good selection and good prices.

Make sure you also purchase a RentalCover.com policy to cover your vehicle against any common damages such as tires, windscreens, theft, and more at a fraction of the price you would pay at the rental desk.

The roads in the Northeast are generally very good and a sedan or economy car should deliver you to most of New England’s top destinations. Only in the most remote portions of the Great North Woods, will the roads be so bad that you need 4×4 or at least high clearance.

If you’re on a road trip in New England during the winter and want to go to the mountains, you will definitely need all-wheel or 4-wheel drive.

Getting Insured for a Road Trip through New England

Concerned about staying safe in the USA? Well don’t be! Just make sure you’re insured, and you drive carefully.

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

New England is no doubt one of the most idyllic regions of the US. Quaint coastal towns and some of the best foliage in the country are but two reasons to take a road trip here–but there are so many more.

Hopefully, you now feel more prepared on where to go and what to do on YOUR New England road trip.

But rest assured that regardless of which spots you’re bound to find beauty, history and a whole lot of delicious seafood.

So what are you waiting for? The open, rural roads of New England awaits!

Updated February 2023 by Samantha Shea

And for transparency’s sake, please know that some of the links in our content are affiliate links . That means that if you book your accommodation, buy your gear, or sort your insurance through our link, we earn a small commission (at no extra cost to you). That said, we only link to the gear we trust and never recommend services we don’t believe are up to scratch. Again, thank you!

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Wow! great article and suggestions.

thank you for all of the advinces it helps, can t wait to visit New England Vermont Maine, xxx

Lake placid in the Adirondack Mountains also a try while stop. There are several private and New York State campgrounds nearby.

Thank you for mapping this all out. I live in New England and would love to visit many of these places.

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The Flexible New England Road Trip Itinerary You Need in 2024 ❤️

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Are you planning the ultimate New England road trip? Let me help! After exploring New England for more than 20 years, I have put together this comprehensive guide to exploring this charming region. The best way to see New England is by car, and this 2-3 week itinerary offers a grand tour of New England, covering the best places to visit , especially for first-time visitors.

Spanning Connecticut, Massachusetts, Maine, Vermont, New Hampshire, and Rhode Island, this itinerary shows you the best of New England, from quaint coastal towns to lush mountain landscapes. The itinerary is also well-paced to allow you to spend time seeing the sites, enjoy local activities, and cross items off your New England bucket list . And, the itinerary is flexible and can be adapted to your needs, interests, and desired trip length.

Whether you’re in for the full journey or seeking shorter road trip variations (I’ve included those, too!), this guide caters to your wanderlust, ensuring a memorable and personalized exploration of New England’s beauty. Let’s go!

PS: Pop this New England playlist on—it’s perfect for a road trip!

Table of Contents

New England Road Trip FAQ

When’s the best time of year to road trip new england.

New England is gorgeous in all seasons, but for the easiest driving (and best New England road tripping experiences), summer and fall are ideal.

If you want the fall foliage experience, late September and early October are the key weeks to plan for. Of course, these times of years are also peak tourist season, so expect more traffic and higher hotel prices.

(PS: If you want to do a shorter road trip or a route that’s perfect for fall, check out my 7 day New England Fall Road Trip itinerary!

One of my favorite times of the year in New England is mid to late May. The weather is beautiful, and the region’s roads and attractions are generally less busy. The budding greenery is especially gorgeous and fresh, too.

Early September can also be lovely, just after kids have returned to school and summer has ended. Expect crisp temperatures and leaves just beginning to change colors.

A winter road trip may be doable, but remember, New England can be quite snowy, so you’ll want to have a reliable vehicle outfitted with snow tires, and you’ll need to stay aware of changing weather conditions and road closures.

How many days do you need for a road trip to New England?

You need 2-3 weeks for a comprehensive road trip around New England. This is the ideal amount of time needed to cover the major highlights of all six New England states.

If you don’t have that much time, you can still pack a lot into a shorter trip. A minimum of 7 to 10 days is ideal for a thorough yet relaxed New England road trip. For a 7-10 day trip, consider my Southern or Northern New England itineraries, or do shorter segments of the full 2-3 week itinerary.

Where should I start my road trip through New England?

I’ve started this New England travel itinerary in Boston, as it’s the biggest city in New England and home to a major airport, Boston Logan International. This airport is easy to fly into and rent a vehicle. Boston is also a great destination on its own, so my itinerary includes a couple days exploring the city.

Ps: Ready to rent a car for your New England drive? Click here to find the best rates on rental cars !

The Perfect New England Road Trip Itinerary

Days 1 & 2: boston, massachusetts.

You’ll start your New England excursion from Boston, Massachusetts: an absolutely fantastic city.

Boston is a well-known place that’s filled to the brim with history. From famous historical events like the Boston Tea Party to its reputation as a modern-day sports town, you’ll never be bored here.

Some great things to do in Boston :

• Visit the North End and dine on amazing Italian food . Don’t miss grabbing cannoli from Mike’s Pastry and Modern Pastry.
• Stroll around quaint Beacon Hill
• Tempt your taste buds with a Boston Food Tour
• Go shopping on classy Newbury Street
• Follow the Freedom Trail to learn Boston’s revolutionary history
• Join an expert-led walking tour for a more in-depth experience of the city
• Check out one of the many great Boston museums, including the Museum of Science which I especially love
• Join a Boston Duck Tour and ride in one of the famous amphibious vehicles

Hotel Suggestion in Boston: Fairmont Copley Plaza

Need more guidance for Boston? Check out my post on The Top Things to Do in Boston for first timers , and I’ve also got some recommendations on where to grab coffee, breakfast , a beer, or a bite to eat in Boston , too !

PS: Looking for a shorter road trip from Boston? Check out my New England trip itinerary focusing on the journey from Boston to Acadia National Park .

Days 3 & 4: Newport, Rhode Island

On Day 3, drive from Boston to Newport. This is a straightforward route, with about 2 hours of drive time. Glitz and glamour. That’s what you’ll find in Newport, Rhode Island. This town is perhaps best known for its iconic Gilded Age mansions . These opulent buildings were once the summer cottages of America’s rich and famous families.

Today, many of them have been converted into museums that you can wander through and admire some of New England’s opulence past.

Some of my favorite things to do in Newport:

• Visit a mansion or two. I recommend The Breakers if you only have time for one of Newport’s mansions
• Hop on this fun Gilded Age Mansions Tour, which takes you around via trolley
• Stroll along the scenic Cliff Walk
• Dine at the White Horse Tavern, America’s oldest operating restaurant

Hotel Suggestion in Newport: Hotel Viking

For further Newport ideas : Click here to read more about the top things to do in Newport, including beaches, restaurants, hotels , and vacation rentals too!

READ NEXT   15 Festive Things to Do for Christmas in Newport RI

Day 5: Mystic, Connecticut

Mystic, Connecticut is a wonderful little seaside town that feels like a must-do on a New England adventure. It is one of my favorite places in New England, and there is plenty to do here: history, culture, art, sailing. And, for seafood lovers, Mystic’s coastal location offers a variety of delicious seafood dining options

Like pretty much every other scenic New England town, there’s a cute little downtown area with great shopping, dining, and activities.

A few terrific things to do in Mystic:

• Explore Mystic Seaport , a historic shipyard and museum destination you could spend hours touring
• Watch the Mystic drawbridge (the Mystic River Bascule Bridge) go up, especially while enjoying some Mystic Drawbridge Ice Cream !
• See the adorable beluga whales at Mystic Aquarium
• Browse the epic shops in Olde Mystick Village including my personal favorite: Alice’s Haunted Little Bookshop

Hotel recommendation for Mystic: The Whaler’s Inn

Further reading on Mystic: Check out my tips for all the fun things to do , best restaurants to eat at , and the best places to stay in Mystic!

READ NEXT   25 Best Beach Towns in New England for Coastal Fun

Day 6: Litchfield Hills, Connecticut

As you roadtrip New England, your next destination is the enchanting Litchfield Hills . This is another easy drive day, as the distance from Mystic to the Litchfield region is a short 2 hours. And if you’re traveling in the fall, the Connecticut fall foliage along this route creates a magical backdrop. To me, this area in the northwest corner of the state is a hidden gem .

Here you’ll find all the classic New England pastimes you know and love. In particular, there is an abundance of outdoor activities (hiking, paddling, fishing) as well as exceptional antique shops.

The Litchfield Hills make up a large portion of this region, and include towns such as Torrington, Woodbury, Kent, Cornwall, and Washington (very English sounding names, aren’t they?)

A few excellent things to do in the Litchfield Hills:

• Live out your Gilmore Girls Dreams. This region is well known for being the inspiration for the iconic tv show that perfectly encapsulates New England small town charm .
• Grab ice cream from Arethusa Farm
• Go covered bridge chasing – Bulls Bridge in Kent has a worthwhile nearby hiking trail
• Hike to Campbell Falls, a beautiful waterfall (this trail technically takes you over the border into Massachusetts, too, so it’s a 2-for-1!)

Recommended hotel in the Litchfield Hills: The Mayflower Inn & Spa : legend has it that it was the inspiration for Lorelei Gilmore’s inn, the Dragonfly.

READ NEXT   18 Wonderful Weekend Getaways from Boston

Day 7: Lenox, Massachusetts

Continue on your New England road trip into the Berkshires of Massachusetts . Here you will encounter art, nature, and culture combined. This region has been very popular among vacationers for many years.  And the town of Lenox is the center of it all.

Best things to do in Lenox:

• Enjoy a concert at the famous Tanglewood (these are a staple in summer, and you can hear everything from leading symphonies to folk singers like James Taylor
• Take in a performance at Shakespeare & Company. This theatre produces excellent shows; I’ve been twice!
• Take a hike on one of the area’s many scenic trails
• Step back in time at the Ventfort Hall Mansion and Gilded Age Museum, a 1890s home that’s open for tours.
• If you are interested in literature, you may also wish to stop by the Mount, Edith Wharton’s turn-of-the-century estate.

Where to stay in Lenox:

More resources for your trip to Lenox and the Berkshires: 🍁 Best Restaurants in Lenox 🍁 10 Charming Cabins in the Berkshires 🍁 Best Hikes in the Berkshires

Day 8: Manchester, Vermont

Finally, you’ve made it into the spectacular state of Vermont (my personal favorite, if you couldn’t tell). It’s a fairly easy drive from the Berkshires in Massachusetts up to Manchester in the southwestern corner of Vermont, only a couple of hours. And this is another route that is especially glorious if you opt to do a New England fall road trip .

Manchester is one of the most beautiful places in Vermont, marrying quaint village charm with touches of modern luxury. It’s no surprise that it’s very popular among travelers.

Some of my favorite things to do in Manchester:

• Tour Hildene , the beautiful Lincoln family home (Yes, some of Abraham Lincoln’s children lived here!)
• Drive to the top of Mt. Equinox on Skyline Drive (or consider hiking the trail up to the summit)
• In the fall, pick pumpkins from the patch at Equinox Valley Nursery (and don’t miss the cider donuts!)
• Shop til you drop at Manchester’s many outlet stores
• Dine at the stately Ye Olde Tavern
• Pop into Northshire Bookstore , one of the leading independent bookstores in New England

Hotel Recommendation for Manchester: Kimpton Taconic Hotel

More resources on Manchester: Read my entire Manchester VT travel guide for more of the top Manchester activities, as well as these articles on the best restaurants , breakfast spots , and hotels in Manchester .

READ NEXT   25 Best Hikes in New England: New England Hiking Options for Everyone

PS: If you’re very interested in exploring Vermont, a trip through Manchester, Burlington, and Stowe make the ideal Vermont road trip itinerary .

Day 9: Burlington, Vermont

Just around 2 hours north of Manchester (taking the beautiful and scenic Route 7) you’ll find yourself in Burlington: Vermont’s biggest city. It’s also often mislabeled as Vermont’s capital, but that honor goes to Montpelier. Still, you’re likely to run into Bernie Sanders in either town!

Burlington is where my husband and I lived for several years. It’s a fantastic town that is hip, artsy, and full of good, local food . Seriously, in Vermont, you need to eat. There’s so much delicious cheese, coffee, beer, maple syrup, and much, much more.

To get you started on your culinary adventures, check out this post on my favorite Burlington breweries and bars , and this one on my beloved coffee shops. Oh, and don’t forget to enjoy brunch in BTV . We do breakfast here right.

The gem of Burlington is Lake Champlain, the sprawling, sparkling lake that the city overlooks. Here is the chance to go sailing, stand-up paddleboarding, or take a ferry across to New York state.

If you’d prefer to stay on dry land, visit one of the many beautiful parks and natural areas. Burlington is amazing for outdoor activities. If you want to get moving, the Burlington Bike Path stretches for miles, hugging the lake’s edge. This is ideal for running or cycling. You can even rent bikes right on the bike path.

More epic things to do in Burlington VT:

• Sail on Lake Champlain on the Spirit of Ethan Allen cruise
• Walk down Church Street for shopping, eats, people-watching, and more
• Hike Mt. Philo, a nearby easy hike with the payoff of a fantastic view

Hotel recommendation in Burlington: Hotel Vermont

Even more resources for your Burlington trip:  🍁 21 Hikes Near Burlington VT to Add to Your Bucket List  🍁 10 Can’t-Miss Free Things to do in Burlington VT  🍁 9 Incredible Day Trips from Burlington VT 🍁 Where to Stay in Burlington VT in 2023: Best Burlington Hotels

PS: Considering visiting Burlington in 2024? It’s one of the cities that the total solar eclipse will pass fully over on April 8, 2024, so start planning ASAP!

Days 10 & 11: Stowe, Vermont

From Burlington, head south on I89 to Exit 10. From there, you’ll take the scenic Route 100 past Waterbury and out to Stowe. When people think of the classic Vermont places, they’re likely thinking of Stowe.

It’s absolutely gorgeous: a charming town surrounded by mountains. The short Main Street and its side streets boast a white-steepled church, an old-timey general store, and a ski museum.

Simply put, Stowe is adorable. I have been to Stowe countless times and I highly recommend it as one of the premier New England road trip destinations!

Wonderful things to do in Stowe:

• Traverse the trails and property at the Trapp Family Lodge , and grab a beer afterwards at their European-style brewery and Bierhall
• Shop the adorable shops on Main Street
• Visit a haunted covered bridge if you dare (Emily’s Bridge)
• Spend a day skiing on one of the area’s fantastic ski mountains
• One of my number one tips: on your way to Stowe, stop by Cold Hollow Cider Mill for all things apple (a must-visit in the fall) and the Ben & Jerry’s Ice Cream Factory tour .

Where to stay in Stowe: Field Guide Lodge , Topnotch Resort , or the Trapp Family Lodge

More on Stowe: I have an entire post dedicated to Things to Do in Stowe, Vermont, the best restaurants , the best breakfast , the best hikes , the best hotels , everything!

READ NEXT   15 Gorgeous VRBO & Airbnb Stowe VT Vacation Rentals (2023)

READ NEXT   Stowe Vermont in Summer: 11 Fun Things to do for All Ages

Days 12 & 13: The White Mountains, New Hampshire

No adventure in New England could be complete without some mountain time. And this is especially true if you’re planning a New England fall road trip .

New Hampshire’s White Mountains are impressive and exciting. They’re the tallest in New England (with Mount Washington tallest of all) and offer spectacular hiking and more. There are several places you could base yourself during this portion of the road trip, but I recommend North Conway, Lincoln, or North Woodstock, as they each offer lots of amenities and accommodations, and are a reasonable distance from the most popular attractions in the region.

Unmissable things to do in the White Mountains:

• Take in some of the coolest natural wonders of the White Mountains , such as the Basin, a granite “pothole” that is found at the base of a waterfall in Franconia Notch State Park
• Go hiking! This is the #1 item on any New Hampshire bucket list . And here is a guide to some of the best hikes in New Hampshire .
• Meander through Flume Gorge. This is a natural ravine that formed over many years and now a hiking trail with a boardwalk passes through it. This is a wonderful hike with some amazing scenery. Another spot that is extra special with the fall foliage
• Clark’s Trading Post in Lincoln, an old-fashioned New Hampshire classic
• A scenic drive along The Kancamangus Highway. This epic stretch of road runs 26 miles between Lincoln and Conway and is one of New Hampshire’s most scenic roads . There are many great spots to stop and explore further and this is undoubtedly one of the best places to see New England fall foliage.
• Shop in North Conway, and don’t miss Zeb’s General Store for a taste of pure nostalgia.
• Tube or paddle in the Saco River. On a friend’s recent bachelorette party trip, we used Saco River Tubing and had an absolute blast!
• Near Bartlett you can stop by Diana’s Baths, a beautiful area of cascading waterfalls and gentle pools. On a hot summer’s day, it’s the perfect place to cool off.

Where to Stay in the White Mountains: Lumen Nature Retreat

More White Mountains travel guides:  🍁  Best Things to Do in North Conway, NH  🍁  Best Things to Do in Lincoln, NH  🍁  Best Things to Do in Franconia, NH  🍁  15 Amazing Cabins in the White Mountains, NH

READ NEXT   Your Guide to Mt Washington NH: The Highest Peak in the Northeast!

Days 14 & 15: Portland, Maine

Finally, the last state on the great New England road trip. This is Maine, “the way life should be.”

Maine is massive so there’s no way to do the state justice in this itinerary; I’m essentially covering a few of the must-see areas. You could spend weeks on a road trip of Maine alone. (See also these  8 autumn scenic drives in Maine delivering up insane fall colors).

If you do wish to explore the rest of Maine (and you absolutely should) I recommend taking a look at my epic list of 50+ Fun Things to Do in Maine , as well as this guide to the top places to visit in Maine . But let’s continue with our amazing road trip!

Stop for a bit in Portland, a modern portside town that may surprise you. There’s a hip city right on the water in Portland, Maine, and this is a hot spot for restaurants, coffee shops, breweries, bakeries , and entertainment .

Fun things to do in Portland:

• Visit a brewery. Beer lovers will be happy to know that Portland has 18 breweries all its own .
• Check out one of several lighthouses in the area . There are 5 less than 20 minutes’ drive from Portland, including the iconic Portland Head Light.
• Grab some of that famous Maine lobster.
• Stuff your face with Maine potato donuts from local staple The Holy Donut
• Walk the pretty Old Port and patronize the eclectic shops and restaurants
• Don’t miss dining at Hot Suppa , a West End restaurant where I enjoyed the best breakfast of my life (and a spectacular maple latte)
• Traveling with kids? The Children’s Museum of Maine on Thompson’s Point is a total blast!

Portland hotel recommendation : Hotel Francis in the West End

Further resources for discovering Portland:  🍁 The Best Things to Do in Portland, Maine  🍁 Weekend in Portland Itinerary  🍁 7 Spots for the Best Breakfast in Portland Maine  🍁 14 Exceptional Airbnb Portland Maine Rentals 🍁 12 Best Hotels in Portland Maine

Days 16 & 17: Acadia National Park and Bar Harbor, Maine

Now we travel north to Bar Harbor. Admittedly, it looks like a far drive on the map. In reality, from Portland to Bar Harbor is just over a 3-hour drive. And trust me, visiting Mt. Desert Island is SO worth it.

Bar Harbor is the seaside town that will be your base for exploring Acadia National Park . You will be in awe over this beautiful part of Maine. Here is where rocky cliffs tumble into the sea, with iconic lighthouses at the top.

There’s abundant wildlife on land and in the sea, and countless opportunities for terrific hiking.

But the region is not just about the outdoors. Bar Harbor has lovely shops, restaurants, and extremely cozy inns . Truly, the region is ideal for travelers of all kinds. You’ll also find great camping, cabins , and vacation rentals in and near Acadia, too.

My top recommendations in Acadia National Park and Bar Harbor:

• Tackle the exhilarating Beehive Hike, that involves a bit of climbing and rewards you with unparalleled views
• Order popovers at the Jordan Pond House (delicious!)
• Take a whale watch or other wildlife tour from Bar Harbor
• Drive up Cadillac Mountain before dawn to catch the sunrise from the first place light touches in the Continental US
• Marvel at the natural wonder of Thunder Hole
• Bike the Carriage Roads in Acadia National Park

Bar Harbor hotel recommendation: The Bar Harbor Inn

More on Acadia: Check out my 3 Day Bar Harbor and Acadia National Park Itinerary for an awesome trip!

Read Next :  10 Coastal Towns in Maine That are Hidden Gems

Day 18: Portsmouth, New Hampshire

Your New England driving tour itinerary is nearing its end, but you’ve got a few more stops to make—-stops you won’t want to miss.

Portsmouth is first. We’re back in New Hampshire now! Between Maine and Massachusetts, New Hampshire is home to a very small strip of coastline. The hub of the Seacoast is Portsmouth, a small yet lively city with a great deal of history. You can see colonial architecture all over this beautiful city.

Taking a New England winter road trip? Portsmouth should definitely be on your list, as they do a month of celebrations and events with Vintage Christmas, one of the most magical New England Christmas celebrations !

Best things to do in Portsmouth:

• Strawbery Banke Museum: an outdoor living history museum.
• Dine at one of the many awesome restaurants: Portsmouth has become a major foodie destination in recent years
• Go shopping at the numerous boutiques around town. Some standouts: Gus & Ruby Letterpress , Pickwick’s Mercantile , and G. Williker’s Toy Shop
• Be surrounded by books and grab a tasty beverage at Book & Bar
• Wander the lovely Prescott Park
• Attend some award-winning theatre at Seacoast Repertory Theatre

Hotel suggestion in Portsmouth: The Hotel Portsmouth

Further Portsmouth NH travel resources for your trip : 🍁 The Best Things to Do in Portsmouth, NH 🍁 Top 10 Bars in Portsmouth NH

READ NEXT   18 Magical New England Christmas Towns that are Straight Out of a Hallmark Movie (Updated 2023)

Day 19: Salem, Massachusetts

Your final stop is the historically infamous Salem, Massachusetts. And though you’ll definitely want to spend time exploring its history with the Salem Witch Trials, there’s plenty to do in the area that isn’t witchy, too.

You can hit the highlights of Salem in one day, or extend for another 2-3.

If possible, you don’t necessarily want to plan your trip to Salem to coincide with Halloween. Although the town has a distinct, fun vibe this time of year, October is also its busiest and most crowded month.

No matter when you go, however, there are definitely some things not to be missed:

• Go to The Witch House, an atmospheric home you’ve definitely seen on Instagram, and a building that is one of the only Salem locations with direct ties to the witch trials. (One of the judges lived here).
• Get witchy in the magickal shops. Whether you want something more fun and touristy, or you’re after the real deal, Salem has a wide range of shops selling all kinds of goods.
• Tour the House of the Seven Gables
• Walk the neighborhoods around Federal Street and admire the stately historic homes
• Find the Hocus Pocus film locations! (Use my guide to take a DIY Hocus Pocus tour )
• Get spooked on a nighttime ghost tour ( top recommendations here !)
• Grab a photo with Samantha at the Bewitched Statue

Hotel recommendation for Salem : The Hawthorne Hotel or Hotel Salem (they have a great rooftop bar)

More on Salem: Check out its great restaurants , scope out some of its haunted history , and maybe even stay overnight in one of Salem’s classic New England inns or Airbnbs ! Nearby towns of Rockport, Gloucester , and Marblehead are worth visiting too if you’d like to explore more of this area of coastal New England.

READ NEXT   12 Fun and FREE Things to Do in Salem MA

Day 20 / End: – Boston, Massachusetts

You did it! You’ve completed an epic New England road trip! Congratulations! You’ve seen some of the prettiest places in the country, and you did it all by car!

Days 21+: Optional Add-Ons: Cape Cod/Nantucket/Martha’s Vineyard

You may be wondering why I didn’t include some of New England’s coastal gems on this New England road trip itinerary? I did this because destinations such as Cape Cod , Nantucket, and Martha’s Vineyard are harder to get to and don’t fit in well with the traditional road trip format. After all, Nantucket and Martha’s Vineyard are islands, so they are not an easy destination to access without in-depth planning.

Not only are they more complicated to travel to, these Massachusetts coastal destinations are terrific and truly worthy of their own vacations . I highly recommend devoting a trip specifically to exploring New England’s amazing coast.

If you wish to add to your road trip, by all means, hop in the car and continue the drive to Cape Cod. From there you can easily take a day trip to Martha’s Vineyard or Nantucket. And I hope these resources will help you as you plan:

More travel ideas here:

• 25 Things to Do on Cape Cod (Besides the Beach!)
• 13 Best Hotels on Cape Cod: Where to Stay on the Cape
• 10 Best Hotels on Nantucket: Where to Stay for a Nantucket Getaway
• 25+ Fun Things to Do in Martha’s Vineyard

The Ultimate New England Road Trip Map (2-3 weeks)

The map below includes all of the destinations I’ve outlined above.

In need of some extra New England road trip ideas? If you’re limited on time, check out my Northern and Southern New England road trip itineraries. These are ideal for 5 day, 7 day, or 10 day New England road trips. Your own personal planning maps are below!

Northern New England Road Trip 7-10 Day Itinerary

• Woodstock, VT
• Waitsfield, VT
• Lincoln, NH
• Portland, ME

Here’s a great New England road trip route if you just don’t have time to go everywhere, but you want to see the highlights of northern New England. In any trip you’ll have to make some choices about what to see and what to miss, sadly, but with this road trip itinerary, you’ll definitely have a broad experience of Northern New England.

This one week New England itinerary contains many of the same stops you’ll find on the ultimate version (that covers all six states). But this one also has the addition of Woodstock, Vermont, which is a classic New England spot, really a ‘Currier and Ives town.’

Southern New England Road Trip 7-10 Day Itinerary

• Provincetown, MA
• Newport, RI
• Providence, RI
• Stonington, CT
• Litchfield Hills, CT
• Gloucester, MA

The Southern New England road trip route is ideal for those who really seek a coastal trip, or who aren’t quite as interested in exploring the mountains. This trip adds a whole bunch of extra stops so you can really dive into coastal New England.

It gives you a feel for the more outdoorsy areas of these southern New England states, too, as the itinerary brings you through the Berkshires, and through charming parts of Connecticut. Definitely an option for a lovely New England summer road trip itinerary.

Shorter Scenic Drives in New England

Are you just looking for a short scenic route that allows you to see dramatic coastal cliffs, mountainscapes, scenic countryside, and more of New England’s charm?

Whether you’re looking for fall scenic drives in New England, beautiful routes along the coast, or just a short yet pretty New England drive, you might just find what you’re looking for on this list of short, scenic drives in New England.

Scenic Drives in New Hampshire

The Coastal Byway (Route 1A)

Location: Portsmouth to Seabrook 

Distance: 18.5 miles 

Where to Stop:  

• Hampton Beach
• Surf Portsmouth , Portsmouth 
• Strawbery Banke Museum , Portsmouth

Robert Frost Scenic Byway

Location: Southern New Hampshire

Distance: 43 miles (The Old Stagecoach Byway and the Robert Frost Byway combined) 

Where to Stop: 

• Robert Frost Farm State Park , Derry 
• Civil War Memorial, Chester
• Matthew Thornton House, Derry 
• Town Beach, Hampstead

New Hampshire Route 112 (Kancamagus Highway)

Location: Conway to Bath

Distance: 56.39 miles 

• Sabbaday Falls 
• Albany Covered Bridge 
• Swift River Lower Falls  
• Russell-Colbath House 
• Sugar Hill Scenic Overlook

The Lake Winnipesaukee Loop

Location: The Lakes Region 

Distance: 97 miles

• George’s Diner , Meredith 
• Mt. Major Trail, Alton 
• Dewey’s Ice Cream Parlor and Cafe , Center Harbor 
• Cotton Valley Rail Trail , Wolfeboro 
• Abenakee Tower , Tuftonboro

Scenic Drives in Maine

• Moosehead Lake

Location: Kennebec and Moose River Valley

Distance: 59 miles

Where to Stop:

• Lily Bay State Park
• B52 Crash Site
• Mount Kineo
• Stress Free Moose Pub & Cafe

U.S. Coastal Route 1 

Location: Kennebunkport to Bar Harbor

Distance: 200 miles

• Goose Rocks Beach , Kennebunkport
• Portland Head Light , Cape Elizabeth
• Old Orchard Beach Boardwalk, Old Orchard Beach
• The Holy Donut, Portland
• Farnsworth Art Museum, Rockland
• Jordan’s Restaurant , Bar Harbor

Acadia All American Road from Trenton to Acadia

Location: Trenton to Bar Harbor

Distance: 40 miles

• Thunder Hole
• Bar Harbor Inn & Spa

Scenic Drives in Vermont

Location: Wilmington to Jay 

Distance: 184 miles

• Molly Stark State Park, Wilmington
• Dot’s Restaurant , Wilmington
• The Vermont Country Store ,  Weston
• Green Mountain Sugar House ,  Ludlow
• Moss Glen Falls, Granville
• Ben & Jerry’s Factory , Waterbury
• Cold Hollow Cider Mill ,  Waterbury Center
• Trapp Family Lodge ,  Stowe

Route 9 – The Molly Stark Byway

Location: Brattleboro to Bennington 

Distance: 40.1 miles

• Vermont Country Deli , Brattleboro
• Creamery Bridge, Brattleboro
• Southern Vermont Natural History Museum, West Marlboro
• Hogback Mountain Scenic Lookout, Wilmington
• Bennington Battle Monument, Bennington
• The Apple Barn and Country Bakeshop – Bennington

Location: Bennington to Burlington 

Distance: 122 miles

• The Bennington Battle Monument, Bennington
• The Robert Frost Stone House Museum , Shaftsbury
• Cider donuts at the Equinox Valley Nursery , Manchester
• Downtown Murals, Rutland
• Woodchuck Cider , Middlebury
• The Burlington Waterfront – Burlington
• Church Street/Downtown – Burlington

Rhode Island Scenic Drives

Ocean drive.

Location: Fort Adams Park to Bellevue Ave

Distance: 10 Miles

• Castle Hill Lighthouse
• Brenton Point State Park
• Fort Adams Park
• The Breakers
• Marble House
• Rough Point
• The Red Parrot Restaurant

Scenic Drives in Connecticut

Connecticut state route 169.

Location: Norwich to Woodstock

Distance: 36 miles

• Lisbon Meadows Park, Lisbon
• Prudence Crandall Museum , Waterbury
• New England Center of Contemporary Art, Brooklyn
• Roseland Cottage , Woodstock

Connecticut Shoreline Drive

Location: New Haven to Stonington Borough

Distance: about 80 miles (depending on which routes you take!)

• Eat in Little Italy, New Haven
• Hammonasset Beach State Park, Madison
• Harvey’s Beach, Old Saybrook
• Rocky Neck State Park, East Lyme
• Mystic Aquarium, Mystic

Scenic Drives in Massachusetts

The berkshires.

Location: Stockbridge to Williamstown

Distance: 35 miles

• Norman Rockwell Museum , Stockbridge
• Berkshire Botanical Garden,  Stockbridge
• The Mount, Edith Wharton House , Lenox
• Berkshire Museum, Pittsfield
• Hancock Shaker Village, Hancock
• Mount Greylock , North Adams
• Massachusetts Museum of Contemporary Art , North Adams
• Williams College – Williamstown

Essex Coastal Scenic Byway

Location: Gloucester to Newburyport 

Distance: 24 miles

• Hammond Castle Museum, Gloucester
• Crane Wildlife Refuge, Essex
• Eat at the Clam Box , Ipswich MA
• Plum Island Beach, Newburyport
• Maudslay State Park, Newburyport

Wrapping Up this Northeast Road Trip

I hope this New England travel guide has given you all the information you need to help you plan a trip to the region’s most exciting and gorgeous places. With multi-day options to choose from and choices that are great for every season, I have aimed to cover all of the top places to road trip throughout these six amazing states.

Even more resources for your New England adventures: 🍁 25 Fantastic New England Day Trips 🍁 Hidden Gems in New England: 15 Secret Places to Visit 🍁 Best Fall Foliage New England Tours Worth Your Money

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The ultimate 10-day new england road trip itinerary.

New England, with its quaint villages, idyllic landscapes, rich history, and mouthwatering culinary experiences, is a treasure chest of delights waiting to be unlocked. From the rugged beauty of the Maine coastline to the vibrant, artistic vibe of Providence, this is a region that never fails to enchant.

If you’re up for the crisp smell of the ocean mingled with pine trees, the rustic charm of cobblestone streets lined with centuries-old houses, and the taste of the most succulent seafood freshly plucked from the sea, then you have to start planning your New England road trip!

» You might be interested in a shorter version with this Boston to Bar Harbor road trip itinerary.

» Looking for more travel inspiration in the United States ? See our U.S. Summer Vacation Ideas and 12 U.S. National Parks to Visit . Here are a few more fabulous U.S. Cities to visit .

The only real problem is deciding what to do and see and how to fit everything into ten days. Lucky for you, we’ve done this road trip multiple times and have passed through these states on a number of different trips, so we have the knowledge to help you plan an amazing time on one of the best road trips in the United States .

Table of Contents

Essential New England Road Trip Info

Comprising six states – Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont -there’s a lot of ground to cover during a New England driving tour. It’s not a small amount of driving, despite how close together many of these states are. So if you’re planning to embark on this road trip, keep this in mind.

You can either fly into a set starting point – we recommend Boston – or you can drive in from where ever you’re located in the United States. In any case, you’re going to need a car – either your own or a rental car . If you’re renting, we suggest going through Discover Cars to get the best deals from all the top car rental companies in one place.

How to Get to New England

If traveling from Europe or another destination outside the States, you’ll fly into Boston for this itinerary. Considering the region’s most popular international airport, Boston Logan International Airport (BOS) is where your trip will start and end.

If Boston doesn’t work for you, you can also fly into New York City , Philadelphia, or even Washington, DC. It will just take you a little longer to drive to the start point of this road trip, but there is plenty to see along the way.

When Should You Do on a New England Trip?

Unless you’re a winter die-hard, the best time to visit New England is undoubtedly during the fall, from September to December, or spring, from March to June. 

Fall is when the landscape takes on a magical element with changing colors in every shade of gold, orange, red, and brown imaginable. Aside from that, the crisp, clear fall air and the New England sun bursting through the morning mists are second to none, making it one of the best fall destinations in the USA .

If you can’t swing a fall road trip, the second best time is during spring. This is before the heat of the summer really sets in, so temperatures will be mild and enjoyable. I would definitely not go in summer, if at all possible, because it can get really hot and humid.

New England Road Trip Itinerary

Are you ready to buckle up and join me on a 10-day road trip across these six picturesque states? I’m thrilled to share this thoroughly curated itinerary that will ensure you make the most out of this journey, exploring the hidden gems as well as the must-see spots.

Whether you’re a history buff, a foodie, a nature enthusiast, or simply someone who enjoys the thrill of exploring new places, this 10-day New England road trip has something for everyone. So pack your bags, put on your favorite road trip playlist, and let’s hit the road.

Boston, Massachusetts (Day 1)

After arriving in Boston, Massachusetts , you can jump directly into the first day of your trip by visiting Boston. Drop off your bags at the hotel and explore Beantown (as it’s locally known). 

In a city defined by a rich history and vibrant sports culture, you’ll find a million historical things to see alongside plenty of sports bars to grab a beer in at the end of your day. While there’s no way to see the best of Boston in one day, we suggest you include these highlights on your first day:

• Walk the Freedom Trail past some of the most important sites that shaped the American Revolution
• Explore the Boston Tea Party Ships and Museums
• Head to the Italian cuisine-filled North End of Boston for either lunch or dinner
• Grab a few snapshots of America’s most photographed street, Acorn Street
• Visit the Boston Library and marvel at its exquisite architecture

Where to stay: The Newbury Boston

Salem, Massachusetts & Portland, Maine (Day 2)

Your second day of this New England vacation itinerary involves the first stretch of road to tackle. Heading out north via the Essex Coastal Scenic Byway (or Route 127), you’ll drive for about 40 minutes to reach Salem.

Infamously known for being the site of the Salem witch trials of 1962, the town is a global epicenter for everything occult. If you’re visiting during October, prepare for an overload of everything spooky. No matter when you’re in town, here are some spots you shouldn’t skip:

• The Salem Witch Museum
• Salem Witch Trials Memorial
• The House of the Seven Gables

When you’re done exploring spooky Salem, jump back on Route 127. After about an hour and forty minutes, you’ll reach Portland, Maine. 

Similar to its west coast counterpart in Oregon , Portland, Maine, is a city with a bustling passion for the arts, the outdoors, and local microbrews and distilleries. Arriving in the city, you can leave your bags at your hotel and set out for a taste of Portland.

Some of the top things to see and do while you’re in town include:

• Visit Fort Williams Park and the Portland Head Light
• Tackle a brewery tour of Portland to some local craft breweries
• Shop the local boutiques and specialty shops of Old Port
• Grab a sunset view along the Eastern Promenade
• Eat lobster rolls at Luke’s Lobster on the pier

Tours to look out for while you’re in Portland:

• Old Port Culinary Walking Tour
• Cusco Bay Sea Kayaking Tour
• A Walk Through Time Tour in Portland 

Where to stay: Portland Regency Hotel & Spa

Bar Harbor & Acadia National Park, Maine (Day 3)

Your third day along this New England trip requires an early start and a three-hour drive, but the rewards are totally worth it. Driving from Portland to Bar Harbor, the beach town gateway to Acadia National Park, prepare for some out-of-this-world scenery.

Along the route, you’ll pass through a few towns worth a stop. The first is Bristol, where you can spend a minute or two at the Pemaquid Point Lighthouse , then stop at the Camden Hills State Park in Camden to see the view from the top of Mt. Battie.

After dropping off your belongings at your overnight spot in Bar Harbor, it’s time to head into Acadia National Park. You need a U.S. Park Pass to get in. If you’re going to be visiting more than one park in the year, you should definitely consider getting the America the Beautiful annual pass, which is just $79.99 from REI.

On Maine’s largest island, Mount Desert Island, the 47,000-acre Acadia National Park has dramatic mountains, picturesque lakes, and endless miles of hiking trails. It’s one of the biggest draws to this part of the U.S.

The top three things to add to your Acadia itinerary include:

• Hiking to the summit of Cadillac Mountain (vehicle reservations are required for Cadillac Summit Road from May 25 through Oct 22). Book online.
• Kayaking on Swan Lake
• Biking or driving the Park Loop Road. The Park Loop Road can be very crowded. Have a backup plan if the area you wish to visit is full.

Where to stay: Bar Harbor Inn

White Mountain National Forest, New Hampshire (Day 4)

While you technically did venture into stunning New Hampshire earlier in your road trip, day four is all about heading to and roaming around one of the state’s top attractions. The drive to get there is another 3 hours 30 min drive, so get up early!

Topping most driving tours of New England, especially those focused on New Hampshire, White Mountain National Forest is a beautiful collection of natural landscapes. The best thing about the National Forest is that there are many unique activities to indulge in regardless of what time of year you’re visiting.

• In springtime, thanks to warmer weather and melting snow, the forest delivers the perfect setting for hiking and camping.
• During the summer, you can fill your day by hiking, fishing, or canoeing.
• When fall arrives, you should set out to drive New Hampshire’s scenic Kancamagus Highway.
• Wintertime brings with it a lot of snow-capped mountains fit for winter sports enthusiasts at numerous ski resorts.

Where to stay: The Inn at Thornhill & Spa

Stowe, Vermont (Day 5)

Once you’ve said farewell to New Hampshire, it’s time to head to NEK or the North-East Kingdom of Vermont. It’s a 1 hour 30 minute drive. Known for its spectacular green mountains, eye-catching lakes, and charming small farms, the state is a buzzworthy must-visit.

On the way to Stowe, you’ll stop in Waterbury for a genuine pilgrimage to the ice cream empire and the original store of Ben & Jerry’s.

Next up is a short 20-minute drive north to the ski resort town of Stowe. This world-famous ski destination showcases an authentic small-town charm, a lively main street, and some iconic steepled churches.

Be sure to check out some of Stowe’s one-of-a-kind local favorites, such as Laughing Moon Chocolates, Shaw’s General Store, and The Deep End (the hippest pizza place in the state). Other options here include:

• Skiing at the Trapp Family Lodge
• Hiking in Green Mountain National Forest
• Heading on a scenic drive on Mountain Road

Where to stay: The Lodge at Spruce Peak

Litchfield & Mystic, Connecticut (Day 6)

Another early start on day six, you’ll drive down the Route 100 Scenic Byway, Vermont’s longest highway, through Wilmington, across the border into Connecticut. First stop of the day? Litchfield; a charming New England town brimming with local history. It’s a 4-hour drive to get there.

Founded in 1719, today, the town is a popular tourist destination known for its antique shops, numerous art galleries, and historic homes.

Delving further into Connecticut, you’ll head east to the town of Mystic. This historic seaport sits snuggly on the Mystic River and is most famous for its maritime heritage and the setting of the 1988 film Mystic Pizza .

Here are some highlights in Mystic:

• Visit the Mystic Seaport Museum , one of the largest in the world
• Explore early colonial farm life at the Denison Homestead
• Dive into some aquatic adventures at the Mystic Aquarium
• Hike a trail or two in Bluff Point State Park

Where to stay: Hilton Mystic

Newport, Rhode Island (Day 7)

Continuing the coastal New England road trip, the next stop along your journey is in Rhode Island. Although it’s the smallest state in the US, it is home to some of the country’s most historic towns, most notably Newport. This is only an hour drive.

This seaside town, once a summer retreat for America’s most wealthy families, boasts breathtakingly stunning mansions built during the Gilded Age and is quite the sight to behold. Beyond that, you’ll find pristine beaches and some of the best seafood in the country here.

When you’re planning your day in Newport, be sure to include these must-do activities:

• Stroll along Cliff Walk, a coastal 3.5-mile pathway hugging the Atlantic Ocean
• Indulge in some retail therapy along Bellevue Avenue and Thames Street
• Head out wine tasting at Greenvale Vineyards
• Tour the famous Newport Mansions
• Explore Bowen’s Wharf or take a boat cruise from Long Wharf
• Relax on the sands of Easton Beach

Where to stay: Newport Marriott

Cape Cod (Day 8)

Next up, and after an entire week on the road, it’s time for some rest and relaxation on the flexed arm of Massachusetts, in Cape Cod, a 1-hour 30-minute drive. Sitting on a peninsula in the state’s southeastern region, Cape Cod has long been a summer destination for the rich and famous.

Now if you’ve ever wondered why New England beach vacations are so popular, the almost 560 miles of coastline that encircle Cape Cod provide a clear answer. Yes, there are many great towns here worthy of a stay, but for this road trip, you’ll spend the day and night in Sandwich.

The official oldest English settlement in Cape Cod, Sandwich, dates back to 1639 and stuns with calm beachfront, quaint eateries, and a vibrant historic district. Fill your day in Sandwich with some of these standouts:

• Breakfast at Cafe Riverview
• Stroll along East Sandwich Beach
• Visit Sandwich Boardwalk
• Explore the Sandwich Historic District
• Indulge in the best lobster in town at Mattakeese Wharf

Where to stay: Sandwich Lodge & Resort

Plymouth, Massachusetts (Day 9)

What would an itinerary for a New England road trip be without a stop in Plymouth? That’s why your second-to-last day in the area is all about exploring the town that dates back to 1620. It’s a 30-minute drive from Cape Cod.

Today this quintessential New England town is most known as the site where the very first Thanksgiving took place and is home to Plymouth Rock. Steeped in history, this is where the Pilgrims first landed way back when.

With all that history, here are a few top spots you should visit while in Plymouth:

• Explore Plimoth Patuxent , a living history museum with a replica of the Mayflower ship
• Grab a few snapshots at Plymouth Rock and delve into the Pilgrim Hall Museum
• Roam around Plymouth’s historic downtown harbor area, home to several notable buildings such as the Plymouth Courthouse
• Cap off your day with a stroll along Plymouth’s famously historic waterfront and catch the sunset over Cape Cod

Where to stay: Thomas Sea Suites at Harbourtown

Boston, Massachusetts (Day 10)

Finally ending your epic 10-day New England road trip, you’re back in Boston . Luckily the drive from Plymouth to Boston is only 45 minutes to an hour, so you can start the day a bit later and still be back in Beantown with some time to spare for any extra activities.

We’d recommend fitting anything you didn’t have time for on day one into your final day. If you’ve got a few extra hours, here are some other Boston highlights to add:

• For history lovers, pay a visit to the USS Constitution Museum or the Paul Revere House
• Art lovers should definitely head to the Isabella Stewart Gardner Museum and the Museum of Fine Arts
• Sports fanatics should take a one-hour tour of Fenway Park or catch a Boston Red Sox game ( check their calendar here )
• For food lovers, be sure to check out our foodie guide to Boston .

Where to stay: Hyatt Centric Faneuil Hall Boston

Wrapping Up Your Road Trip Through New England

There you have it – the best road trip through New England you could possibly do in ten days. Although numerous other attractions and standout activities can be included on any trip, this New England trip itinerary features the best of the best.

Of course, you can play around with other vacation ideas in New England or discover hidden travel tips heading off-the-beaten-path. Now all you have to do is decide when to go and prepare for some exciting road-tripping in New England.

Be Prepared For Travel Planning is the most important part of any successful trip. Do it the easy way:

🧳 Travel Packing List | ✔️ Why You Need Travel Insurance | ✈️ What to Do Before You Leave Home

• Find and book the best hotel (our favorite booking site is Expedia)
• Research flight options (our favorite tool is Skyscanner )
• Book a tour (we always use Viator to find the best tours)
• Rent a car through Discover Cars (they search the best deals for you!)

YOU MIGHT ALSO LIKE

8 Foodie Things to Do in Boston Massachusetts

17 Awesome Places to Visit in the United States

13 Best Cities to Visit in the United States

5 Top Historic Cities in the U.S.

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Laura Lynch, creator and writer of Savored Journeys, is an avid world traveler, certified wine expert, and international food specialist. She has written about travel and food for over 20 years and has visited over 75 countries. Her work has been published in numerous guidebooks, websites, and magazines.

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9 New England Road Trip Itineraries for Any Season

Whether it’s spring, summer, fall, or winter, there’s a road trip (or two) for each season..

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View of Horsehead-Marbella, an historic house near Beavertail State Park.

Photo by Trevor Fairbank/Shutterstock

New England may be known for its autumn reds and yellows, but to us, there’s no bad time to cross the region by car. Officially consisting of the six states of Maine , Vermont, New Hampshire, Massachusetts, Connecticut, and Rhode Island, New England is filled with picturesque seaside towns, mountains, clear lakes, and yep, some of the best fall foliage around. To see the region’s most beautiful sites, head out on one of these great New England road trip itineraries.

1. Vermont 100

• Start: Heartwellville
• Distance: 200 miles
• Recommended season: summer

At 200 miles long, the Scenic Route 100 Byway hugs the eastern edge of the Green Mountains and travels nearly the entire length of Vermont. (Most of Vermont’s ski resorts are located along the highway, so it can actually have fewer cars in the summer than winter.) Cute country stores your thing? Be sure to stop at Vermont Country Store in Weston—it’s been open since 1946 and offers free cheese and maple syrup samples.

Dramatic scenes like these are par for the course along Maine’s coast.

Photo by Shutterstock

2. Coastal Maine

• Start: Ogunquit
• End: Calais
• Distance: 272 miles

Much like California , Maine is also known for its stretch of Route 1, aka “the lobster trail.” This trip crawls along the coastline and passes through Ogunquit, Kennebunk, Portland, Rockport, and more until it hits Canada. Must-dos along the way: Eat at the Clam Shack , on the bridge between Kennebunk and Kennebunkport, snap a photo for the ’gram at Portland Head Light, and visit Project Puffin Visitor Center in Rockland—especially fun with kids in tow.

Cape Cod is known for its beautiful beaches and coast line.

VALORIE DARLING/Valorie Darling

3. Old King’s Highway in Cape Cod

• Start: Sandwich
• End: Provincetown
• Distance: 60 miles

Route 6A is popular in summer, when visitors to the Massachusetts Cape begin their trip in Sandwich and follow the road east to Provincetown, passing cranberry bogs, salt marshes, historic homes, and some of the oldest villages in the United States. Get your lobster roll fix at places like Kate’s Seafood (Brewster) and Arnold’s Lobster & Clam Bar (Eastham). For overnights, head over to South Dennis and stay at the Sesuit Harbor House , originally built in 1735.

The Kancamagus Highway is known for being one of the top spots to see fall foliage.

4. Kancamagus Highway, New Hampshire

• Start: Conway
• End: Lincoln
• Distance: 34.5 miles
• Recommended season: fall

Curving for 34.5 miles on country roads through New Hampshire’s White Mountain National Forest, this drive has earned its place on several “best of” road trip lists, thanks to its picturesque ponds, hiking trails, scenic overlooks, and hairpin turns. Colloquially known as the “Kanc,” the byway draws millions of visitors every year. With the highway’s plentiful hiking trails taking up daylight, spend the night in one of the six White Mountain National Forest campgrounds located on the byway.

This road trip passes through quaint towns like St. Johnsbury, Vermont.

SNEHIT PHOTO/Shutterstock

5. Connecticut River Byway

• Start: South Hadley, Massachusetts
• End: Pittsburg, New Hampshire
• Distance: 242 miles

Another way to reach New Hampshire’s White Mountains is to take the Connecticut River Byway , which is Vermont’s only designated National Byway. Along the way, stop by some of Massachusetts’s historic district villages like Northfield and Montague Center, or take some nature-led detours to Molly State Park in Vermont.

If you’re unable to do the whole route, no worries. In the words of AFAR editor Tim Chester : “Pick a stretch and you can’t go wrong—particularly in fall when the leafy backdrop is painted shades of red, orange, and yellow.”

End your road trip in Burlington, Vermont’s capital.

Shutterstock

6. Burlington to Woodstock, Vermont

• Start: Burlington
• End: Woodstock
• Distance: 132 miles

While several road trips on this list go through Vermont, this road trip itinerary specifically focuses on the state’s delicious dishes . Starting in Burlington, road-trippers can visit the local farmers’ market for breakfast before continuing south on Route 89 to Stowe. Around here, try concepts like Long Trail Brewing Company and Hen of the Wood. The drive concludes in Woodstock, offering local fare from Fat Toad Farm.

7. Mohawk Trail, Massachusetts

• Start: Pittsfield
• End: Greenfield
• Distance: 63 miles

Massachusetts’s Berkshire Mountains and its famed 63-mile Mohawk Trail are the stuff of leaf-peeping legends . Starting in Pittsfield, take Route 7 north until hitting Williamstown, home to Williams College, and continue on Route 2 to Western Gateway Heritage State Park, Natural Bridge State Park, and MASS MoCA, among other attractions. Eventually, you’ll hit the Hoosac Range—where the views only keep getting better. For a stay along the way, consider the Tourists hotel in North Adams.

Winter in Stowe, Vermont, one of the leading ski destinations on the East Coast

8. Skiers’ Paradise, Vermont

• Start: Stowe
• Distance: 80 miles
• Recommended season: winter

Come winter, heavy snow drifts mean good things for skiers in New England. Visit two of the best ski resorts on the East Coast on this road trip, which starts in Stowe and finishes in Woodstock, Vermont. It’s a mere 80 miles between the two towns, but the slopes—and attractions—in each mean you’ll want to spread the trip out over a long weekend. Things not to miss in Stowe: the family-run Alchemist brewery, Stowe Maple Products sugarhouse, and the thin-crust pies at the aptly named Piecasso .

In Woodstock, be sure to carve out time for Richardson’s Tavern , Billings Farm & Museum , and F.H. Gillingham & Sons , a store that has been open for more than 130 years.

9. Quiet Connecticut

• Start: Norwich
• Distance: 40 miles
• Recommended season: spring

If you’re a fan of quaint towns and farmsteads, this road trip from Norwich to Woodstock might be for you. (Fun fact: Woodstock has more dairy farms than anywhere else in the state.) The road clocks in at 40 miles, you’ll want to slow down and take your time—yep, it’s that scenic. Do some birdwatching at Aicher Preserve or Border Woods Preserve before staying at the Inn At Woodstock Hill , where you can enjoy Connecticut’s serenity near the small town of Putnam. Tranquility, is that you?

This article originally appeared online in 2020; it was most recently updated on August 9, 2023, to include current information.

The Ultimate 5 Day New England Road Trip Itinerary

Hello, fellow road trippers! Are you ready to embark on a picturesque journey through New England? This 5-day New England road trip itinerary is designed to show you the best of this region’s charming towns, stunning landscapes, and rich history. As someone who loves hitting the road and has a soft spot for New England’s unique allure, I’m thrilled to share this journey with you.

Day 1: Boston, Massachusetts – The Historic Start

Starting Point – Boston : Begin your New England adventure in Boston, a city steeped in history and culture. Spend your morning walking the Freedom Trail , a 2.5-mile route that takes you to 16 historically significant sites. Don’t miss the Boston Common, the United States’ oldest public park.

Afternoon Exploration : In the afternoon, explore the cobblestone streets of Beacon Hill, known for its beautiful Federal-style rowhouses and quaint atmosphere. Enjoy a meal at one of the local eateries – Boston’s culinary scene is a delightful mix of traditional New England fare and modern cuisine.

Evening in Boston : As evening falls, head to the Boston Harbor or stroll along the Charles River Esplanade for stunning city views.

Day 2: Boston to Cape Cod, Massachusetts – Coastal Charm

Morning Drive to Cape Cod : On your second day, head to Cape Cod, a hook-shaped peninsula known for its quaint villages, seafood shacks, Martha’s vineyard and lighthouses. The drive from Boston to Cape Cod is about 1.5 hours, but take your time and enjoy the scenic journey.

Exploring Cape Cod : Once in Cape Cod, visit the Cape Cod National Seashore for its beautiful beaches and walking trails. Check out Provincetown for its art galleries and vibrant street life.

Overnight in Cape Cod : Spend the night in one of Cape Cod’s charming inns or bed and breakfasts, experiencing true New England hospitality.

Day 3: Cape Cod to Newport, Rhode Island – A Touch of Elegance

Journey to Newport : On day three, travel to Newport, Rhode Island, renowned for its stunning Gilded Age mansions and sailing culture. The drive takes about 1.5 hours, offering beautiful coastal views along the way.

Discovering Newport : In Newport, tour The Breakers, the grandest of Newport’s summer “cottages” and a symbol of the Vanderbilt family’s social and financial preeminence in the Gilded Age. Stroll along the Cliff Walk, a 3.5-mile path that offers spectacular ocean views on one side and opulent mansions on the other.

Evening Leisure : Enjoy an evening in Newport’s historic downtown, dining by the waterfront and savoring fresh local seafood.

Day 4: Newport, Rhode Island to White Mountains, New Hampshire – Into the Wilderness

Morning in Newport : Start your fourth day with a leisurely morning in Newport. Perhaps take a sail around Narragansett Bay or explore more of the town’s historic streets and shops.

Drive to the White Mountains : Mid-morning, begin your journey north to the White Mountains in New Hampshire. This drive takes you into the heart of New England’s natural beauty. The journey is about 4 hours but feels shorter due to the stunning scenery along the way.

Exploring the White Mountains : Upon arrival, immerse yourself in the natural splendor of the White Mountains. Visit Franconia Notch State Park, where you can see the Flume Gorge, a natural granite gorge extending 800 feet at the base of Mount Liberty. The Cannon Mountain Aerial Tramway offers breathtaking panoramic views.

Overnight in the Mountains : Spend your night in a cozy mountain lodge or cabin. The White Mountains region offers various accommodations, from rustic to luxurious, allowing you to enjoy the serene mountain atmosphere.

Day 5: White Mountains to Portland, Maine – A Coastal Finale

Morning Hikes and Scenic Views : Wake up early to catch a sunrise in the mountains. If you’re up for it, enjoy a morning hike; there are trails for all skill levels, offering one last chance to soak in the natural beauty of New Hampshire.

Journey to Portland, Maine : After your morning in the mountains, set off for Portland, Maine, about a 2-hour drive. This charming coastal city is known for its vibrant arts scene, historic Old Port waterfront, and incredible seafood.

Discovering Portland : Spend your afternoon exploring Portland’s cobblestone streets, unique boutiques, and art galleries. The Portland Head Light, a historic lighthouse in nearby Cape Elizabeth, is worth a visit for its picturesque setting.

Evening in Portland : Conclude your New England road trip with a delightful dinner in Portland. The city’s culinary scene is a fusion of traditional New England flavors and innovative cuisine. Enjoy a meal at one of the waterfront restaurants, savoring the fresh catch of the day.

Reflecting on Your New England Road Trip

Your 5-day New England road trip itinerary has taken you on a journey through some of the most picturesque and culturally rich parts of the Northeast. From the historic streets of Boston to the coastal beauty of Cape Cod and Newport, the majestic White Mountains, and the charming city of Portland, you’ve experienced a tapestry of landscapes and lifestyles that make New England unique.

As you head home, you carry with you not just photos but memories of quaint towns, scenic drives, and the warm hospitality of the Northeast. This trip is more than just a journey through places; it’s an exploration of the heart and soul of New England.

I hope this itinerary inspires you to explore the diverse beauty of New England. Safe travels, and may your road trips be filled with discovery and joy. If you need any more tips or insights for traveling in New England or beyond, feel free to reach out. Happy travels!

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Road-Tripping New England: My Suggested Itinerary

I’ve said it before and I’ll say it again: The United States is made for road trips . With its bustling cities, rugged national parks, and delicious eats, the sheer size and diversity of this country never cease to amaze me.

I’ve road-tripped the USA five times, spending a cumulative year exploring its cities, towns, and parks. To me, a road trip is the best way to explore the US. By driving the back roads and getting out of the cities, you really get to see the diversity and natural beauty of the country.

One region in particular that I love to drive around is New England.

Having grown up in Boston and gone to college in Western Massachusetts, I’ve spent a lot of my life in this part of the country. Last summer, I spent even more time here, exploring parts of Maine , Cape Cod, and upstate New York that I had never seen before.

And yeah, I’m biased because I grew up here, but I really do think New England is one of the most special areas of the country. It offers delicious seafood, friendly and welcoming people, incredible natural beauty, charm, and plenty of history.

And, given the fact the region is relatively small, it’s easy to get around, so you can cover a lot of ground in a short amount of time.

If you’re thinking of visiting, here’s a suggested road trip around New England to help you get a feel for the region:  

Days 1-3: Boston, MA

These are some of my favorite things to do in Boston:

• Walk the Freedom Trail – This 2.5-mile (4km) route takes you through colonial Boston. Starting in the Boston Common and winding past Faneuil Hall, the Old State House, and Bunker Hill, this historical walk teaches you about life in colonial and revolutionary times. The tourism board also offers guided tours (tickets are $16 USD).
• See the Museum of Fine Arts – This museum has over 450,000 pieces of fine art, from the pre-Columbian era to Italian Impressionism. It’s one of the best collections in the country. Admission is $27 USD.
• Visit Bunker Hill Monument – The Battle of Bunker Hill in 1775 was one of the first major clashes of the Revolutionary War. While the redcoats won, the Americans wore British forces down more than was expected. The monument stands 221 feet tall; you can climb to the top to enjoy the view (it’s the best view of Boston). (Temporarily closed for restoration work).
• Lounge in Boston Common – This is the oldest city park in the US, dating to 1634. It was once used as communal pastureland by Puritan settlers (they also executed some “witches” here as well). Today, it’s a great place to relax, people-watch, and picnic.
• Visit Harvard – Harvard University is the first and oldest university in the country (founded in 1636, far predating the United States). The campus offers free one-hour tours through the grounds and buildings. Afterward, grab a coffee and people-watch in the alternative and artsy Harvard Square.
• Catch a game at Fenway Park – This is one of the oldest baseball parks in the country (it opened in 1912). Bostonians are die-hard Sox fans, so even if you don’t like baseball, go for the cultural experience. Tickets start around $20 USD for standing room or bleacher seats, and $31 USD for the grandstand. Guided tours of the stadium are offered year-round as well. There are various tour options, but the standard guided tour lasts 90 minutes and costs $25 USD per person.

For more suggestions on what to do in the city (and there’s plenty), check out my free guide to Boston .

Where to Stay

• HI Boston – This is my favorite hostel in the city. It’s clean, spacious, and social, and the staff are super friendly and helpful.

For more suggestions, here is my list of the best places to stay in Boston .  

Days 4-5: Portland, ME

• Visit Peaks Island – This small island is home to around a thousand people. Located just 20 minutes off the coast, it’s a laid-back place to eat, lounge, and check out the quaint shops. There’s also a small World War II museum here, as well as a neat umbrella cover museum (it’s more interesting than it sounds!).
• Try a Holy Donut – Holy Donuts are made from Maine potatoes (which sounds weird, but they are incredibly tasty), so they are at least somewhat healthier than your standard donut. There’s always a line, so try to get there early!
• See the lighthouses – There are several historic lighthouses worth seeing nearby, including the Portland Breakwater (which was designed to look like a Greek monument), Spring Point Ledge (which was built in 1897 and is open for tours on weekends), and Portland Head Light (which was built in 1791).
• Wander Victoria Mansion – This ornate mansion-turned-museum, built in 1860 and declared a National Historic Landmark in 1971, boasts a brownstone exterior and elaborate interior furnishings. It’s incredibly lavish, shedding light on what life was like for the well-to-do in the late 19th century. Admission is $16 USD.

While you’re in Portland, be sure to check out some of the city’s best restaurants, including Duckfat (get the fries), Eventide Oyster Co. (best oysters in the city), and Bite into Maine (best lobster roll in the city). For drinks, head to Rising Tide Brewery.

• Black Elephant Hostel – This hostel has a cool, colorful interior and social atmosphere, and is perfectly located near lots of restaurants and shopping.

Days 6-8: Bar Harbor, ME

Moreover, on the way up from Portland, take Route 1 and stop for food along the way in any one of the numerous historic fishing towns. If you like oysters, stop at Glidden Point Oyster Farm.

Here are some things to see and do in and near Bar Harbor:

• Explore Acadia National Park – This gorgeous national park encompasses forests, lakes, and mountains, and covers a large swath of the Atlantic coastline. It’s incredibly popular in the summer for hiking, biking, camping, kayaking, and more. You could easily spend a couple of days just exploring the park. A 7-day vehicle pass is $30 USD and camping starts at $22 USD per night.
• Visit Abbe Museum – This museum showcases the area’s indigenous history and culture. It’s very informative and sheds important light on a history often overlooked. It’s part of the Smithsonian, so you know it’s going to be good! Admission is $10 USD.

Like the rest of Maine, Bar Harbor has some wonderful places to eat. My favorites were the Travelin Lobster (best lobster roll in the area), Havana (upscale dining), and Rosalie’s (delicious food all around).

• Bar Harbor Manor – This is a cozy hotel right outside Acadia National Park with lots of outdoor space to relax in, free Wi-Fi, and an indoor parlor with a fireplace.

Day 9: Bangor, ME

My favorite places to eat are the Fiddlehead (delicious food all around) and Judy’s (best diner breakfast). For a drink, head to Mason’s Brewing.

Where to Stay Bangor is a small town, so you’ll want to compare prices on Booking.com and Airbnb to see what best suits your budget.  

Days 10-12: Moosehead Lake, ME

Spend a couple of days here relaxing away from the crowds, hiking the plethora of trails, spotting moose, or taking part in all the lake activities on offer.

For dinner or drinks, head to the Stress Free Moose Pub in Greenville.

• Leisure Life – This accommodation is basic, but it’s in a great location (in Greenville), and the staff are super helpful.

Days 13-14: Mount Washington, NH

Some of the best day hikes up the mountain are Tuckerman Ravine Trail (4.2 miles, strenuous), Lion’s Head Trail (4.2 miles, strenuous), and Jewell Trail (5.2 miles, moderate).

Where to Stay You can stay in nearby Gorham or Littleton. Check Booking.com and Airbnb to see what best suits your budget.  

Days 15-17: Burlington, VT

Some of my favorite things to do here are the following:

• Wander Church Street – This pedestrian-only thoroughfare is the heart of the city. Café-hop, browse the bookstores and other shops, and take in the slow pace of life.
• Get out on the water – Spend some time out on the water and soak up the sun. Boat rentals, cruises, paddle boarding, kayaking — you can do it all here. There are also several beaches you can lounge on, with North Beach being the most popular.
• Visit Ben & Jerry’s – This is where the global ice cream brand originated. If you have more time, you can visit the nearby factory in Waterbury and see the “ice cream graveyard,” where Ben & Jerry’s commemorates its obsolete flavors.
• Indulge in craft beer – Burlington is a craft beer mecca, home to over a dozen breweries. Go bar- or brewery-hopping to taste the best the city has to offer. Local favorites include Foam Brewers, Zero Gravity, Fiddlehead Brewing Company, and the Burlington Beer Company.

Where to Stay There are no hostels here, so compare prices on Booking.com and Airbnb to see what best suits your budget.  

Days 18-19: Green Mountain National Forest, VT

Highlights include Thundering Falls (a 140-foot waterfall), the Long Trail (a 272-mile hike and the oldest long-distance trail in the country), and the panoramic view from the 4,000-foot Camel Hump summit.

Since it’s a national forest, camping here is free (unless signs advise otherwise).  

Days 20-22: The Berkshires, MA

Here are some things to see and do:

• Hike Mount Greylock – Standing 3,491 feet tall and located in a state park encompassing over 12,000 acres, Mount Greylock is the highest peak in Massachusetts. There are several trails that lead to the summit (including a portion of the Appalachian Trail). The hike takes around 90 minutes, and the views from the top are absolutely breathtaking — you can see for miles!
• Visit the Norman Rockwell Museum – Norman Rockwell, the prolific American painter and illustrator, spent much of his life in Stockbridge. A museum was established there to showcase his life and works, highlighting the evolution and impact of his art. Admission is $20 USD.
• Explore Natural Bridge State Park – Located in North Adams, this park is home to a natural bridge of white marble (which is over 550 million years old) as well as an old marble quarry. There’s an easy trail around the bridge and quarry, and plenty of relaxing fields and meadows to picnic in. Parking is $20 USD for out-of-state residents.

Day 23: Amherst, MA

Be sure to tour the Emily Dickinson Museum, which commemorates the poet (she was born in Amherst in 1830). The house where she was born and grew up, now converted into a museum, includes artwork, artifacts, clothing, and poetry from Dickinson’s life. There are often events and poetry readings here, so check the website to see what’s on during your visit. Guided tours last 60 minutes and cost $15 USD. Currently closed for restoration work.

As for food, Antonio’s Pizza is a must (they have some really inventive toppings). I ate a lot of it during college! I’m also a big fan of Black Sheep for sandwiches and House of Teriyaki for Japanese food.

Day 24: Back to Boston

It’s just a short two-hour drive back to Boston, so feel free to stop along the way to stretch your legs. There are plenty of places to stop along the way or just do more things in Boston!  

Bonus Destination: Cape Cod, MA

Here are some things to see and do during your stay:

• Go whale watching – From April to October, you can see finback, minke, and humpback whales, as well as dolphins and seals. Tours cost around $67 USD.
• Hike or bike the National Seashore – Created in 1961 by JFK, this park spans over 43,000 acres. There are 11 hiking trails, as well as half a dozen cycling trials. All of them are well marked so it’s an easy way to stretch your legs and take in the beautiful landscape.
• Visit some lighthouses – There are dozens of picturesque lighthouses around Cape Cod, some of which are open to the public. Don’t miss Nauset, Nobska, and Highland lighthouses.

New England is one of the most beautiful parts of the United States. Its size makes it perfect for road trips, offering a nice mix of cities, small towns, and stunning natural beauty. It also has some of the best seafood in the country, lots of hiking and biking opportunities, and some of the friendliest people in the country. I’m proud to have grown up in this region and encourage you to explore my backyard!

Book Your Trip to the United States: Logistical Tips and Tricks

Book Your Flight Use Skyscanner to find a cheap flight. They are my favorite search engine because they search websites and airlines around the globe, so you always know no stone is being left unturned.

Book Your Accommodation You can book your hostel with Hostelworld as it has the biggest inventory and best deals. If you want to stay somewhere other than a hostel, use Booking.com as it consistently returns the cheapest rates for guesthouses and hotels.

Don’t Forget Travel Insurance Travel insurance will protect you against illness, injury, theft, and cancellations. It’s comprehensive protection in case anything goes wrong. I never go on a trip without it, as I’ve had to use it many times in the past. My favorite companies that offer the best service and value are:

• Safety Wing (for everyone below 70)
• Insure My Trip (for those 70 and over)
• Medjet (for additional repatriation coverage)

Looking for the Best Companies to Save Money With? Check out my resource page for the best companies to use when you travel. I list all the ones I use to save money when I’m on the road, and I’m sure they will do the same for you.

Need an Affordable RV for Your Road Trip? RVshare lets you rent RVs from private individuals all around the country, saving you tons of money in the process. It’s like Airbnb for RVs.

Want More Information on the United States? Be sure to visit our robust destination guide on the USA for even more planning tips!

Got a comment on this article? Join the conversation on Facebook , Instagram , or Twitter and share your thoughts!

Disclosure: Please note that some of the links above may be affiliate links, and at no additional cost to you, I earn a commission if you make a purchase. I recommend only products and companies I use and the income goes to keeping the site community supported and ad free.

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The Ultimate New England Road Trip Itinerary

Get acquainted with the birthplace of America on a New England road trip. Discover the quaint coastal towns, famous historical landmarks, and spectacular scenic drives the area has to offer. Our trip includes additional states, but the bulk of our itinerary is in six states: Connecticut, Rhode Island, Massachusetts, New Hampshire, Maine, and Vermont.

It’s for 60 days, starting and ending in Chicago and driving roughly 2,500 miles, but you can adjust it to your liking. Visit one national park, too-many-to-count lighthouses, a few state parks, picturesque small towns, and overindulging on copious amounts of seafood along the way.

If you are looking for more unforgettable adventures, check out these trips: Chicago to L.A. via Route 66 , hiking 500 miles on the Camino in Spain , and a cross country road trip to thirteen national parks.  

When to Visit New England

From our experience and research, there really is no bad time to visit New England. Each season brings something unique to the table.

Winter is cold and snowy but perfect for winter activities such as skiing and snowboarding. The thawing temperatures of spring bring wildflowers and maple syrup. Summer is known for its hot weather and sunny days filled with outdoor adventures. And last but not least, fall welcomes a blanket of blazing colored treetops and great hiking temperatures.

WAIT UNTIL YOU READ WHAT WE HAVE PLANNED! SCROLL DOWN FOR MORE INFO

One of the Top Spots for Fall Foliage in the U.S.

So why did we choose New England this trip? We have had an east coast road trip on our radar for quite some time and especially wanted to visit during the fall. It is touted as one of the best locations for fall foliage in the United States.

Donned in our heavy sweaters as autumn unfolds with rich colors of crimson and gold with the smell of fire and a hint of pumpkin spice floating in the air, I can’t imagine a better time.

Hopefully, from mid-September until the end of October, we will be leaf peeping fools.

Ultimate New England Road Trip Itinerary Summary

Keep Scrolling for our detailed New England Self Drive Itinerary.

Summary starting and Ending in Chicago, Illinois

• Put-in-Bay, Ohio (2 nights)
• Erie, Pennsylvania (1 night)
• Watkins Glen State Park, New York (3 nights)
• Litchfield, Connecticut (1 night)
• Hartford, Connecticut (2 nights)
• New Haven, Connecticut (1 night)
• Niantic, Connecticut (1 night)
• Mystic, Connecticut (2 nights)
• Block Island, Rhode Island (1 night)
• Portsmouth, Rhode Island (2 nights)
• Providence, Rhode Island (2 nights)
• Provincetown, Massachusetts (1 night)
• Falmouth, Massachusetts (1 night)
• Martha’s Vineyard, Massachusetts (3 nights)
• Plymouth, Massachusetts (1 night)
• Salem, Massachusetts (1 night)
• Hampton Falls, New Hampshire (1 night)
• Kennebunkport, Maine (1 night)
• Acadia National Park / Bar Harbor (8 nights)
• Bangor, Maine (2 nights)
• Baxter State Park, Maine (3 nights)
• Lily State Park, Maine (2 nights)
• White Mountains, New Hampshire (6 nights)
• Burlington, Vermont (2 nights)
• Stowe, Vermont (2 nights)
• West Dover, Vermont (7 nights)
• Buffalo, New York (1 night)
• Chicago, Illinois

Day 1: Chicago, Illinois to Put-In-Bay, Ohio

We leave Lake Michigan to head over to Lake Erie, the southernmost lake of the Great Lakes. It is also the shallowest which makes its water temps the warmest.

Our first stop is Put-In-Bay, a small village on South Bass Island. Known for its party-hearty culture, we are determined to not only imbibe a bit but also to discover the hidden gems on the island.

Driving Info: 279 miles, 5 hrs 20 minutes with a ferry ride

READ NEXT: TOP 10 THINGS TO DO IN PUT-IN-BAY

Day 2: Put-In-Bay, Ohio to Erie, Pennsylvania

We were beckoned to drive along the Lake Erie coast when we visited Cleveland a few years ago but didn’t include the ride on that trip. Up the waterline, we go, as we leave Put-In-Bay to explore the small towns and lighthouses along the way.

Who knew Pennsylvania has a sliver of land right on the lake? We stop for the night at Presque Isle State Park, a small park on a sandy peninsula that juts into Lake Erie. If you are interested in renting an RV and starting in Pennsylvania, check out RV Rental Philadelphia, the largest, most trusted RV Rental marketplace with a wide-ranging inventory.

Driving Info: 190 miles, 3 hrs 45 minutes with a ferry ride

RELATED: COOL STOPS ALONG OHIO’S LAKE ERIE COASTAL TRAIL

Days 4 – 6: Erie, Pennsylvania to the Finger Lakes, New York

The Finger Lakes region in New York is known for a series of pristine lakes and beautiful vineyards. The area is also home to a number of hiking trails, breweries, distilleries, and hard-cider producers.

Driving Info: 198 miles, 3 hrs 15 minutes

READ MORE: 3 DAY FINGER LAKES ITINERARY

Day 7: Finger Lakes to Litchfield Hills, Connecticut

Ever heard of the television show, Gilmore Girls ? Today, we reach our first New England state, Connecticut, where the fictional town of Stars Hollow was based on. We are touring the northwest hills in search of magical towns like Washington, New Milford, Bantam, and Litchfield which inspired the creators of the show.

Driving Info: 297 miles, 5 hrs

RELATED: A CONNECTICUT BUCKET LIST FOR YOUR NEXT TRIP

Days 8 & 9: Litchfield Hills to Hartford, Connecticut

And we are off to the state capital of Hartford, one of the oldest cities in the United States. Founded in 1635, we are bound to find some historical places to visit. A few on the list so far are Trinity College, Wadsworth Art Museum, and Bushnell Park.

The one I’m most excited about is the Mark Twain House where he wrote some of his most famous works and raised his family.

Driving Info: 32 miles, 50 minutes

Day 10: Hartford to New Haven, Connecticut

Let’s make our way to the water again, New Haven is situated along the Long Island Sound in southern Connecticut. It’s the first planned city in America and home to Yale, one of the oldest universities in America.

Oh and apparently, home to some of the best pizza in the country. This Chicago-born Midwesterner writes with a probably-not-side-grin. But hey, you never know!

Driving Info: 39 miles, 40 minutes

Day 11: New Haven to Niantic, Connecticut

On our way to Mystic, we plan to take a leisurely drive along the coast to dip in any beach towns with a view. At lunch, we will find our first lobster roll of the trip. The word on the street is that Connecticut’s rolls are not made with mayo, just butter and a squeeze of lemon so it’s a must-try.

Driving Info: 42 miles, 45 minutes

Days 12 & 13: Niantic to Mystic, Connecticut

Never did I imagine a New England road trip would have me hunting down pizza, but stopping at Mystic Pizza is a MUST in my eyes. My love for Julia Roberts isn’t the only reason we are stopping here, the seaside village is brimming with charm and boasts the nation’s largest maritime museum.

Driving Info: 18 miles, 25 minutes

Day 14: Mystic to Block Island, Rhode Island

With a declaration from the Nature Conservancy that Block Island is one of its “Last Great Places,” it was a given that we were going to zip our way over once we cross into Rhode Island. As if dramatic rugged bluffs weren’t enough to put us over the edge (literally and figurately), the 365 freshwater ponds and rolling green hills had us hooked.

Driving Info: 54 miles, 2 hrs 15 minutes with a ferry ride

Plan Your Trip Here: Amazing Things to Do on Block Island

Days 15 & 16: Block Island to Portsmouth, Rhode Island

Portsmouth is our base location for exploring the grandeur Newport Mansions of the social elite like the Vanderbilts and Astors. Ah, the Gilded Age, when the rich were rich and wanted everyone to know it.

After a few tours such as the Biltmore Estate and  Stan Hywet Hall and Gardens, we’ve become obsessed with these over-the-top homes. We can’t wait to stroll the Cliff Walk, a 3.5 mile National Recreation Trail that hugs the Newport shoreline offering gorgeous coastline and mansion views.

Driving Info: 46 miles, 2 hrs 11 minutes with a ferry ride

How to Choose the Best Newport Mansion Tour

Days 17 & 18: Portsmouth to Providence, Rhode Island

Cheers to hitting another state capital! Providence is the cultural hotspot of New England. With a vintage feel in a college town and the most coffee and doughnut shops per capita of any city in the country, I’m sure we’ll keep busy, or at least our mouths will.

Driving Info: 29 miles, 32 minutes

Day 19: Providence, Rhode Island to Provincetown, Massachusetts

Onward to the Cape! Cape Cod that is. And it is here where we will have one of the most anticipated experiences of the trip, a whale watching tour!

Situated at the tip of Cape Cod, Provincetown is a quirky artsy area that also happens to be a jumping point for whale watching tours.

Driving Info: 120 miles, 2 hrs 12 minutes

Day 20: Provincetown to Falmouth, Massachusetts

Today is a day for moseying around the island stopping at captivating waterfront villages and maybe a local food shack or brewery. Since we brought our bikes, we will roll onto the Shining Sea Bikeway, a 10.7-mile path that runs from the coast in Falmouth to Woods Hole and then past to North Falmouth. 

Overnight is at Falmouth so we can get an early ferry over to Martha’s Vineyard.

Driving Info: 68 miles, 1 hr 35 minutes

Days 21 – 23 Falmouth to Martha’s Vineyard, Massachusetts

Just south of Cape Cod and a short ferry ride away sits Martha’s Vineyard, a presidential getaway in my mind. I picture snazzy inns, upscale boutiques, and perfect stately homes; ritzy glamour degraded by the simplicity of the beach… where I will tell no one that our minivan turned campervan awaits us back on the mainland. Read here about all the fun things to do on Martha’s Vineyard Island. 

Driving Info: 19 miles, 1 hour 15 minutes with a ferry ride

Day 24: Martha’s Vineyard to Plymouth, Massachusetts

Advancing north, stop for an overnight at the first Pilgrim settlement, Plymouth, where I’m sure you will have mixed emotions about the small rock that marks the spot.

But the iconic landmark is not what keeps visitors coming back for more.

Driving Info: 55 miles, 2 hrs

Day 25: Plymouth to Salem, Massachusetts

If you haven’t heard of the Salem witch trials then you may be living under a rock. Plymouth rock, perhaps.

Salem is not shy about its history where the word “witch” is displayed all over town. It shouldn’t come as a surprise that a witch museum, cemetery and a house with a supernatural past are on our itinerary.

Driving Info: 64 miles, 1 hr 17 minutes

Day 26: Salem, Massachusetts to Hampton Falls, New Hampshire

Clutching the coast, swing past Manchester-by-the-Sea, Gloucester, Rockport, and Newburyport before crossing over to the next state of New Hampshire.

Make sure to detour to the Hammond Castle Museum, an exotic castle built in the early 1900s by an inventor.

Driving Info: 32 miles, 45 minutes

Day 27: Hampton Falls, New Hampshire to Kennebunkport, Maine

At 18 miles long, New Hampshire’s coastline is short-lived so progress to the state of Maine. It’s hard to believe you’ve hit five of the six New England states already!

Kennebunkport is going to be all about seafood, boats, and shopping.

Driving Info: 43 miles, 50 minutes

Days 28 – 35: Kennebunkport to Acadia National Park, Maine

It’s time for some hiking and biking! Park it in Acadia National Park for at least four days (more if you can swing it) because you’ll be in awe of the beauty around you.

Cadillac Mountain, Sand Beach, Bar Harbor, and Park Loop Road are just a few things on the list of things to see. 

Read about one of the most thrilling hikes in the Northeast that you’ll find within the park. 

Driving Info: 201 miles, 3 hrs 30 minutes

Days 36 & 37: Acadia National Park to Bangor, Maine

The main reason for our weekend in Bangor is to visit with friends, but items like a Stephen King’s house and the world’s largest Paul Bunyan statue might have you putting it on your itinerary as well.

Driving Info: 50 miles, 1 hr 15 minutes

Days 38 – 40: Bangor to Baxter State Park, Maine

Baxter State Park is home to Mount Katahdin and the end of the 2,168-mile Appalachian Trail. Take a few days to explore and hike to the peak of the highest mountain in Maine at 5,270 feet.

Driving Info: 88 miles, 1 hr 35 minutes

RELATED: SEE OUR FAVORITE FREE CAMPING APPS

Days 41 & 42: Baxter State Park to Lily Bay State Park, Maine

At Lily Bay State Park, you’ll find what’s often referred to as Maine’s crown jewel, Moosehead Lake, the largest lake in New England.

It is also known to sprout some bright fall colors and is a great area to spot moose.

Driving Info: 51 miles, 1 hr 35 minutes

Days 43 – 48: Lily Bay State Park, Maine to White Mountains, New Hampshire

The Kancamagus Highway, a 34-mile road through the heart of the White Mountains, is one of the best drives for fall foliage in the United States.

No stores, no houses – just forest; the scenic byway stretches from Lincoln to Conway.

Driving Info: 205 miles, 4 hrs 25 minutes

Days 49 & 50: White Mountains to Burlington, Vermont

Along the shores of Lake Champlain sits a vibrant city with a thriving arts scene and welcoming atmosphere. Vermont’s largest city, Burlington, has a little bit of everything.

Driving Info: 2 hrs 20 minutes

Days 51 & 52: Burlington to Stowe, Vermont

The birthplace of the infamous Heady Topper Beer from The Alchemist Brewery and a stone’s throw away from Ben & Jerry’s factory, I think I’m going to start calling Stowe, the adult playground of Vermont. 

Driving Info: 36 miles, 46 minutes

Days 53 – 59: Stowe to West Dover, Vermont

From Stowe, take the well-known Highway 100, another popular fall foliage route in New England, down along the Green Mountains.

Hopefully, those green mountains will be lit up with scarlet reds, glistening golds, and tangerine orange.

Driving Info: 147 miles, 2 hrs 41 minutes

Day 60: West Dover, Vermont to Chicago, Illinois

At this point in the trip, you could take an extra night to stop at the one and only Niagara Falls in New York. Otherwise, that’s a wrap folk!

60 days and a whole lotta unforgettable memories!

TIP: For those of you that would like to close the loop, head further south to the Berkshires of Western Massachusetts. A popular destination for fall foliage, cultural attractions, and outdoor fun. 

Driving Info: 13 miles, 13 hrs 36 minutes

See Below for a Map of the New England Road Trip Itinerary.

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Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

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13 Responses

So, I’m a fan of this trip. You had me at Gilmore Girls, Mystic Pizza and then solidified how much we are connected with Salem and Bangor.

I have wanted to do a Fall Foliage trip like this forever. I think I might try to make this happen one year…soon. I can’t wait to see your photos on the IG.

Dang Travelers

It has been on our list of places to get to for awhile now so we are ecstatic to finally be making it happen. I’m cracking up because when I (Angela) was making the itinerary I totally watched a few Gilmore Girls episodes and the movie, Mystic Pizza to get pumped! Leaving the GG reference out to Save though. He didn’t know that’s why I planned that area until a few days ago! LOL We will get started on all your planning so all you have to do is find the time. Thanks for following Kristi!

You didn’t include Mt. Washington and the cog railway. You should try to hit they in!!! I think you’re gonna love Block Island, Burlington, Acadia. The coast of ME. Mystic is nice. Portsmouth, RI has a ride the rails along the waterfront. Check that out. Too bad you are missing Boston!

We will be hitting Mt Washington in the White Mountains but didn’t know about the cog railway! So excited to explore Rhode Island and Connecticut or shall I say #47 and #48 of my states list. Dave really wanted to go into Boston but figured we could do it on another trip when we fly in. Always expensive and difficult to worry about parking in big cities but othwrwise we would have loved to. Thanks for the tips Cheryl!

Your trip sounds awesome. I cannot wait for all the pictures and to hear all about it. I would make a detour in Maine and stop in Freeport, Maine and go to LL Bean store. It is an absolute must see. It is open 24 hours (at least it used to be) and there are 9 floors and each one is better/more exciting then the next. It isn’t just clothes either. My husband enjoyed it as well and he isn’t a shopper.

Top Things to Do on Block Island: A Travel Guide – Dang Travelers

[…] SEE OUR ENTIRE 60 DAY ITINERARY […]

Found your trip itinerary and will definitely be putting it to use! Not too often do you find trips starting in the Midwest! I just went through and copied and pasted all the trip info you suggested. Or is there a printable version of this that I completely missed somewhere? Thanks so much for sharing!

Hi Nicole! I do not have a downloadable itinerary as of right now. Sorry, hopefully copying worked just fine. You’ll love it out east!

Cheryl Archambault

For anyone wanting to specifically see the foliage start in farthest north of New Hampshire generally around the 3-4 week of September. Foliage is peak around Concord during Columbus Day Weekend; but cool or rainy weather can change that. Encourage you to take a jacket and go up the Cog Railway to the top of Mt. Washington. It could be covered in snow there! In Rhode Island Block Island is lovely. Ferries leave from Pt. Judith or Newport. Newport is lovely and don’t miss seeing Waterfire in Providence. Acadia National Park and Bar Harbor and Boothbay is wonderful. East to west Vermont in Fall is a dream. Rte2 is a very scenic ride.

Thanks so much Cheryl!

my husband & I want to do an abbreviated version of your trip. What time of year did you do this trip? I have heard Sept is the best time for lobster but Oct is the best time for foliage.

We started right after labor day in September but took about 3 months. That year the fall color was starting to come in late September and lasted through the third week of October. Inland and lower elevations started earlier with Acadia National Park at peak around the second week of October. Unfortunately, every year is different so it’s hard to get it just right when planning ahead of time!

Thank you for the itinerary. It is a great start for me. I don’t have quite as much time but I hope I can get to a lot of the highlights as I’m starting from Virginia.

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New England Summer Road Trip (One Week Itinerary)

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My mother grew up in a small lake town in Western Connecticut. I suppose that’s how it all started, the annual family New England road trip. 

I was born and raised in NJ, but really, m y brothers and I grew up New England. Our summer and holiday weekends were often spent on that grueling strip of I-95 that stretches between New Jersey and the northern part of the country.

Between my grandparent’s house in Connecticut, a beach house in a small fishing village on the coast of Rhode Island, and my father’s annual meeting in Bar Harbor, Maine, I got to know New England intimately. It has some of my happiest childhood (and later, adulthood) memories.

Long after my family had drifted apart and those road trips stopped I continued to explore, taking my own family (AKA Joe and Della pup) along this very route.

New England is downright gorgeous.

It’s allll the cliches. Small cities filled with charming cobblestone streets, tiny, snow covered homes, and old-school Main Streets. 

It’s also small geographically. Like, you can drive from the tip of Connecticut to the tip of Maine in half a day, small. 

Though we won’t be doing that here. Here, we’re showing you how to take your time and absorb some of the most scenic spots — filled with the best food, obviously — in a week’s time.

In this one week New England road trip itinerary we’re sticking to the New England coast, perfect for cruising in the Summer or Fall months.

P.S. Going for longer than a week? Check the end of the post for suggestions on how to extend your road trip through other New England hot spots.

Table of Contents

Steps to Plan the Best Road Trip in New England

1. Plot your route

Where are you leaving from? What are your “can’t misses?” Where do you want to stay? Our itinerary below is a guide…you can follow it exactly (because it’s freaking awesome) or you can pick and choose which works best for you to form your own path.

2. Check your route against the weather. 

This is so often overlooked! Plan your route as loosely as possible. This way, you can quickly pivot if the weather is threatening to ruin your plans. It allows you more flexibility, so when there is rain forecast on the day you want to go to Acadia National Park, you can easily switch it to another.

Obviously take this with a grain of salt…weather is weather, and in New England, weather is usually unpredictable, so bring a sense of humor. As they say up around here:

“There’s no such thing as bad weather, just bad clothing” or, my personal favorite, “If you don’t like the weather, wait 15 minutes” 

3. Follow your heart

This applies to every travel experience. If you plan an activity and it sucks, BAIL. If you find a local seafood restaurant on the side of the road where a grandma-looking lady is frying fish …slam on those breaks immediately. 

When should you go on a new england road trip?

I’m going to say that SUPER annoying thing we all hate and say…it depends! Road trips in New England can vary depending on the weather. Let’s break it down by season:

How does this itinerary work?

This itinerary leaves from the New York City metro area, but you can hop on or off at any point along the way. 

If you’re in upstate New York simply head west until you reach I-95 (or check out these New York day trips instead.

Leaving from further South? Trying extending the road trip through Philadelphia– stopping for a pizza break –or go for a scenic run on the New Jersey shore .

One Week New England Road Trip Itinerary

Day 1 Connecticut

Start your New England road trip off by cruising north from New York City and into Connecticut, possibly the most underrated of the New England states. The southern part of the state is mostly made up of wealthy New York City suburbs, so we’ll skip right over that. 

The first stop will be a welcome break from the traffic you’ll likely be sitting in on I-95. New Haven is known for two things:

1. Yale and–more importantly in our book– 2. P izza

We’re the type of people who took a train to Naples just to eat pizza for 6 hours straight, so you know we couldn’t miss the opportunity to explore what folks claim to be the best Napoli style pizza this side of the Atlantic.

The best pizza in New Haven is debated with a ferocity that you probably don’t need to involve yourself in as a brief visitor.

Instead, just trust us and head to Modern Apizza for the best pie in the city. 

Or, if you want to do the tourist thing, check out the clam pies at Frank Pepe Pizzeria Napoletana. It wasn’t our favorite, but its been around for almost 100 years (which earns lots of respect in its own right).

Expect to wait in line for hours if you choose this spot.

If you’re one of THOSE people who don’t like pizza, there’s a great selection of taco trucks in a parking lot next to I-95. This is the spot to sample actual Mexican food, like beef tongue and tripe. 

And if you don’t like pizza or tacos…you’re honestly on the wrong blog.

Once you’re done consuming your body weight in pizza and/or tacos, hop back in the car and drive an hour north to Mystic, Connecticut. 

This little seaside town is a straight charmer. Fun fact: it’s also where the ultra-80’s classic Mystic Pizza was filmed, much to my mother’s delight. It’s worth spending a night here to tuck into one of the many B & B’s and snuggle up next to your boo.

Mystic Aquarium is great for all you fellow marine nerds (good for the kiddos and rainy days, too). When you wake up in the morning, head to Kitchen Little at Mystic River Marina, order the Lobster Benedict, and then call me immediately to thank me for starting your day off with such a marvelous treat on your tongue.

Where to Eat in New England

• Pizza at Modern Apizza , 874 State St, (203) 776-5306 http://modernapizza.com/
• Tacos at T aco trucks , 351 Long Wharf Dr in Long Wharf Park, varied
• Lobsters Benedict at Kitchen Little , 36 Quarry Rd, (860) 536-2122 https://kitchenlittle.org/

Where to Stay in Mystic, Connecticut

We’ve actually never stayed in Mystic ourselves so can’t personally recommend anything, but taking a dip in the gorgeous looking pool at House of 1833 Bed and Breakfast feels like something we’d be very into.

Days 2-3 Narragansett, Rhode Island

The smallest state in the union is also one of our favorites. Rhode Island is not, in fact, an island as I’m sure you’re all aware. However, thanks to its 400 miles of coastline, it still lives up to its “Ocean State” nickname. 

Rhode Island beaches are the main thing that draws us here every summer, though you could easily spend time praising the marshy and wooded trail walks as well.

Up north near Newport, beaches are steep rocky cliffs lined with old mansions. Down in the southern edge of the state–our fave–beaches are soft, sandy strips backed by grassy dunes.

Specifically, it’s the beaches in Rhode Island’s South County that have captured our hearts. They’re the reason we go back year after year, aside from the fact that we have family there.

Plus, this area is filled with some of our favorite seafood restaurants of all time.

These are some of our favorite South County beaches:

• Galilee Beach – little bit more of a local scene on a GORGEOUS beach
• Narragansett town beach – go surfing (or hang and watch!)
• Point Judith Lighthouse – rocky cliff facing out to the sea, can catch sunset views here depending on the time of year

Narragansett is a great little town to use as your home base here. It’s the home of URI and has a smattering of chill beach bars and delicious food.

Between beach trips, h ead into town for a fresh juice or smoothie at the hole-in-the-wall Crazy Burger , or do a fancy pants date night over at Coast Guard House , where you can sip on chowder while watching the Atlantic Ocean crash into the rocks outside the oversized glass windows.

If you really want to enjoy the scenery and the locavore seafood here, though, hop in the car and ride over to Matunuck Oyster Bar . 

Perched on the marsh where the oysters are grown, owner and aquaculturist Perry Rasso has grown this restaurant into a gorgeous indoor-outdoor space, serving up oysters as soon as they’re pulled from the water.

Our trips to Matunuck Oyster Bar usually consist of us waiting two hours for a table outside, cracking open a bottle of champagne, and watching the tide roll in and out while we slurp down dozens of our favorite salty little bivalves.

Honestly, I could (and usually do) spend a week here in Rhode Island and go nowhere else. It is the ultimate combination of rest, sweet salt air, and ultra-fresh seafood that my body craves after a long winter.

But you’re on a mission to explore New England on this road trip, so stop off for a night or two and then head North.

Where to Eat in Narragansett, Rhode Island

• Oysters at Matunuck Oyster Bar , 629 Succotash Rd, Wakefield, RI (401) 783-4202 https://www.rhodyoysters.com/
• Chowder and clam cakes at Iggy’s Doughboys , 1151 Point Judith Rd, Narragansett, RI (401) 783-5608 https://www.iggysri.com/chowda
• Coast Guard House , 40 Ocean Rd, Narragansett, RI (401) 789-0700 https://thecoastguardhouse.com/
• Crazy Burger , 144 Boon St, Narragansett, RI (401) 783-1810 http://www.crazyburger.com/

Where to Stay in Narragansett, Rhode Island

We’ve stayed at the Aqua Blue Hotel before which was ok (the location is AMAZING literally steps from the beach and Coast Guard House for dinner, although you pay for that) but we’ve heard GREAT things about The Break Hotel .

Days 3-4 Massachusetts

Hop back on I-95 and head north until you hit Boston, your next stop on this New England road trip.

Boston is a little city that feels like a little city, but with a bunch of strangely aggressive folks who drink a lot. I don’t mean that as an insult…Boston is a lot of fun. And being from New Jersey where people also tend to be angry at random times, these are my kind of people.

In all seriousness, Boston epitomizes so much of what is great about New England in an urban setting. The cobblestone streets are crammed with history and lined with tiny row houses that look straight out of a Charles Dickens novel. 

Fenway Park , the oldest operating baseball stadium in the country, sits in a charming downtown neighborhood with great food.

Boston’s Little Italy in the North End still has pasta cooking grannies rolling out dough by hand, and there are a delightful craft beer and food options everywhere you look.

The harbor is kept shockingly clean (coming from New York) and love it or hate it, Cambridge and Harvard are downright stunning.

Spend a full day exploring the historical sites, catching a Red Sox game, or touring the eclectic Harpoon brewery on the harbor. 

I’m also a sucker for the original Legal Sea Foods, though it’s recently moved and I’m not sure it’s worth it without the nostalgia factor.

Before you continue on your New England road trip, make time for a quick pit stop in Ipswich, MA.

It’s an adorable little town jutting out into the Atlantic Ocean that also happens to have some of the best fried clams EVER! Argue it…I dare you.

Then, continue North… 

Where to Eat in Massachusetts:

• Clam Box , 246 High St, Ipswich, MA (978) 356-9707 http://www.clamboxipswich.com/
• Legal Sea Foods , 55 Boylston St., Chestnut Hill, (617) 277-7300 https://www.legalseafoods.com/
• Giacomo’s , 355 Hanover St (617) 523-9026

Where to Stay in Boston, Massachusetts:

There’s literally an option for anyone when it comes to hotels in Boston. Click here to see a full hotel list with 100’s of options in every budget and style.

Day 4-6 Maine

Maine, you crafty, beautiful genius! How did you get to be so wild and stunning?

The lobsters…the pine trees…the rocky majestic coast…Maine is the epitome of when you just can’t even.

Here’s how you spend 2 days in Maine.

First off, go to Acadia National Park . Just go right there. Because as beautiful and amazing as much of the rest of the state is…Acadia is the masterpiece of it all.

Plus, with only a couple of days to explore, it’s the easiest way to see the best of what Maine has to offer.

Camp inside the park (Blackwoods Campground is the best if you can get in) or head downtown to Bar Harbor for a home base. Hotels here aren’t cheap, though, so plan ahead for this.

Take whale watching trips off the coast, hike the winding ocean-view hugging trials, scramble up rock faces, or just eat lobster rolls every hour on the hour.

One time, Joe ate lobster for every single meal for a week straight in Bar Harbor…it wasn’t cheap or particularly healthy, but it was impressive. And, he was happy. 

You can see the first sunrise hitting the continental US from Cadillac mountain (note: this gets really crowded) and head down for early morning blueberry pancakes at Jordan’s Restaurant.

Or, head out to pick wild blueberries yourself. They’re much smaller than the traditional grocery store ones, all the easier to pop them in your mouth like candy.  In season, you can find them hugging the trails, or you can stop by a local farm.

Where to Eat in Maine:

• Fresh boiled lobsters at Thurston’s Lobster Pound , 9 Thurston Rd, Bernard, ME (207) 244-7600 https://www.thurstonforlobster.com/
• Lobster rolls at Thirsty Whale , 40 Cottage St, Bar Harbor, ME (207) 288-9335 https://www.thirstywhaletavern.com/
• Blueberry pancakes at Jordan’s Restaurant , 80 Cottage St, Bar Harbor, ME (207) 288-3586 http://www.jordansbarharbor.com

Where to Stay in Bar Harbor, Maine:

Bar Harbor Inn is where I stayed every time growing up. Even after decades in use, it’s managed to stay modern and refined. I love the charming rooms, elegant feel, and actually good breakfasts here. Oh, and it just so happens to be on the ocean (think listening to the waves crashing on the rocks beneath you…DREAMY). Granted…my parents were floating the bill then, it’s not cheap, but SO worth it if you can swing it.

Click here to book The Bar Harbor Inn if you want to ball out on some luxury.

Or try Camping at Acadia National Park .

Day 7 On the road back home.. .

Head home, OR just never leave, We won’t judge.

Not sure where to stay? Use the search box below to find the best hotels in Connecticut, Rhode Island, and everywhere else in gorgeous New England.

Options to extend your New England road trip:

Add a night, day, or as long as you’d like on through some of these great additions:

• Portsmouth, NH – this trendy little harbor town gets its fair share of local tourists but isn’t often on the radar for outsiders. Be in the know and visit.
• Portland, Maine – one of our all-time favorite cities, Portland feels more like a small town, albeit one on the rugged Maine coast that happens to have exceptional dining.
• Burlington, Vermont – a hippy college town at it’s finest, lake-front Burlington is a bit out there but well worth the segway.
• Cape Cod, MA – come for pictures of the wood-shingled beachfront mansions, stay for the local pubs serving up piping hot seafood chowder and freshly fried, fish.
• Block Island , RI – this reminds us a lot of Ireland, it shares the romantic feelings and rolling, green hills. We like to take the ferry over and rent a bike, which will easily take you around the entire island.
• Kennebunk, Maine – Which we hit up on a different new England road trip (also where that lobster roll pic was born!!)

Road Trip Destinations in New England

It’s worth time to come up to New England just to stop at any one of these spots.

• Acadia National Park – For the unreal, oceanfront hiking.
• South County Beaches – For pristine, sandy beaches.
• New Haven – For the pizza and tacos.
• Boston seaport – For the charming, small city feel.

What is there to do in New England in Summer?

Soooo many things! 

• Bake your skin on the sandy beaches
• Hiking! Best in the Northern parts in my opinion (Vermont, New Hampshire, and Maine) but there are still great forested trails in Connecticut and marshland walks in Rhode Island
• Kayaking, canoeing, and stand up paddleboarding on lakes, rivers, marshes, and the Atlantic Ocean…oh my!
• Eating all of the fresh, local seafood like a maniac

New England Road Trip Map

We are the dynamic running duo that run this site. Lovers of new places, bridges, and all the food.

Returning to NYC / New England for first time in 20 years for family road trip. . Grew up on Pepe’s and Modern Pizza, and many other things you mentioned about Connecticut were spot on, love the recommendations throughout your articles. Will be using a lot of this information to help plan out our New England Summer vacation. Thank you for taking the time to share.

Thanks Frank! So glad you found it helpful

Should we travel on over to Plymouth since we’d be so close?

Hey Charlene, that’s a great idea! We’ve actually never visited Plymouth but from what I’ve heard about it I’m sure it would make a great addition

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New England Road Trips- 10 Spectacular Routes + Where to Stay

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New England road trips are experiences you’ll never forget. With picturesque towns, fresh seafood, and a whole different culture of its own, you’re sure to fall in love with New England.

Whether you are searching for the best fall road trips in New England, scenic drives on the coast, a romantic or weekend getaway, we have got you covered. All you have to do is grab your sunglasses and hit the road!

I teamed up with experienced travel bloggers to share this list of the best New England road trips.  These getaways showcase the best places to visit in New England, plus recommendations on where to stay and eat.

When is the best time to visit New England on a road trip?

The iconic Portland Head Light. Portland, Maine

New England is probably one of the rare places that is gorgeous regardless of which season it is. Although summer and fall are ideal for making the most out of a New England road trip, the best time to visit this region depends on the kind of New England you want to experience.

In summer, New England offers super-fresh seafood in various coastal restaurants, while fall comes with glorious foliage and wineries to enjoy a delicious tasting. Summer and fall are also great for hiking, biking, and driving.

Spring in New England comes with fields full of blooming flowers,  a sight you don’t want to miss.

If you’re a fan of skiing or snowboarding, New England winters are for you. From relaxing by the fireplace and gazing at the stars to skiing by the ocean, winters in New England are sure to be memorable. However, this season is not ideal for road trips, as it can be difficult for driving.

TABLE OF CONTENTS

• Vermont – Route 100
• New Hampshire – Kancamagus Highway
• New Hampshire – White Mountains
• Massachusetts – Boston to Berkshires
• Maine – Portland to Bar Harbor + Acadia National Park
• Rhode Island’s South Coast to Block Island
• Connecticut – Hartford to Norwalk
• Vermont – Stowe to Woodstock

Massachusetts – Martha’s Vineyard to Cape Cod

• Maine – Ogunquit to Portland

Best New England Road Trips in the Fall

Vermont  – route 100 for stunning new england fall foliage.

By Amy Hartle, New England With Love

For an incredible fall foliage road trip in New England, you can’t ignore Vermont’s Route 100. This is one of the best scenic drives in Vermont, and especially in the glorious autumn season. Vermont is known for boasting some of the best foliage in all of New England, and the whole of the USA.

Route 100 is a great road trip route because the road snakes from north to south through the center of the state. It passes over large swaths of the Green Mountains, meaning your drive brings you along high elevations where the color is just gorgeous.

Route 100 also passes through many small towns and villages that are worthy of stopping! The Vermont Country Store in Weston is located right along this road, a classic old-fashioned New England shop that sells amazing items and some yummy food, too.

Further north, along Route 100 in Waterbury, travelers MUST stop at the Cold Hollow Cider Mill. This cider mill fresh presses its own delicious cider, cooks up some of the best apple cider donuts in Vermont, and simply has an incredible fall atmosphere. You feel it the moment you walk in. It is one of my favorite places in all of Vermont.

You can continue to the end of Route 100 in Vermont, but I recommend ending your trip in the magical town that is Stowe. This is a scenic and charming spot right out of a magazine.

New Hampshire – Kancamagus Highway – A perfect New England scenic drive

By Nikki Ortan from Attractions of America

Widely hailed as one of New England’s best fall foliage drives, the Kancamagus Highway stands out in a region regarded nationally for its scenic drives .

The Kancamagus Highway – found on Route 112 and known to frequenters as ‘The Kanc’ – boasts 34.5 miles of breathtaking views cutting east to west through the state of New Hampshire. Foliage lovers have long gone out of their way to plan a path on Route 112, and The Kanc is such a draw that entire vacations can be built around getting the most out of the highway.

To simply drive through the highway is free, but to park along the trail will require a day pass for $5 that will enable you to explore all the trail has to offer. Many of the path’s overlook areas feature bathrooms and small service areas, and you can pick up a permit and a map for the highway at the Saco Ranger Station or the White Mountains Visitor Center.

Starting in Conway and ending in Lincoln is the most common route. Heading from east to west, some sights to keep in mind are the lower falls scenic area, rocky gorge scenic area, Russel-Colbath historic site, Sabbaday Falls and Swift river, and the Lily pond, to name a few. There is also ample opportunity to camp, and taking advantage of any of the options is highly recommended. Check out spots such as the Hancock , Big Rock , and Blackberry Crossing Campgrounds, with rates as low as $20 per night.

New Hampshire – Another can’t-miss fall route in the White Mountains

View from Artists Bluff in New Hampshire – Image by Frank Parrott

By Frank Parrott of NothingButNewEngland

The White Mountains in Fall is a truly magical place with a vibrance of colors that highlight the beauty of the surrounding peaks.  One of the best road trip through the Whites starts by staying in the heart of the mountains, the Omni Mount Washington.  Located near the base of New Hampshire’s highest summit, the surrounding view is nothing short of spectacular.

A great tour of the area starts with heading to Artists Bluff.  This scenic spot is located a short 25 mins away from the resort at the beginning of the beautiful Franconia Notch region.  Park in the Cannon Mountain parking by Echo Lake Beach and cross the street to start the hike to Artists Bluff.  It’s worth the effort to see a view that will be that memorable.  No fear if you can not hike to the top, you can still see amazing views by just driving through Franconia Notch.  This also leads to the next stop, a swirling glacier falls called the Basin.

Head back towards the Omni for a quick lunch but be sure to stop to admire the roadside falls on the way.  The Silver Cascade and Flume Cascade are picturesque falls easily seen from your car.

After your lunch, keep heading on route 302 for 50 mins to the Pinkham Notch area.  Park at the AMC Pinkham Notch Visitor area for another not-to-miss view.  If you’re lucky, you may even be treated to a moose sighting.

Artist’s Bluff in New Hampshire – Image by Frank Parrott

Massachusetts – Boston to Berkshires, for quaint New England towns

By Bharat and Supriya from fun travelog

Come fall season, and many residents of Massachusetts head to Berkshires in the western region of the state. Only a two and a half-hour drive from Boston, the area offers a different surrounding from the cityscape.

Surrounded by mountains (a part of the Appalachian Trail passes through this region), this beautiful hilly region is marked by small towns, farms, orchards, farm-to-restaurants, cafes, outdoor spaces, and lovely B&Bs. Start your trip in Boston and head first to Shelburne Falls, a quintessential New England small town that is two hours away. Walk over the Bridge of Flowers, grab a quick bite and stretch your feet. Next, visit the Mohawk Trail State Forest in nearby Charlemont. Another trail for viewing fall foliage is the 11-mile long Ashuwillticook Rail Trail in Lanesborough.

If you love museums, head to either Mass MOCA in North Adams, the Norman Rockwell Museum, or Clark Art Institute for an afternoon. North Adams, Williamstown, Great Barrington, and Lenox are some of the top towns to visit in the Berkshires. Fall is also a good time to try warm apple cider donuts from Hilltop or Bartlett Orchards.

Best New England Scenic Drives on the Coast: 

Maine – portland to bar harbor road trip + acadia national park.

Acadia National Park – Image by Stephanie Woodson

By Stephanie Woodson from Explore More Clean Less

Take the leisurely full-day route along the coast to connect these two delightful cities, driving about 160 coastline miles in about 3.5 hours. You’ll be able to gaze out on the water for the bulk of the drive, in addition to cruising through quiet, touristy towns.

Starting in Portland, take the twisty road northeast, with a first must-see along the Penobscot Narrows Bridge. Visitors can check out the bridge observatory 420 feet up in the air and look into the distance along the waterway.  Further north, take the afternoon to tour around Boothbay Harbor on a wildlife excursion hunting for seals, whales, and puffins!

Pulling into Bar Harbor, don’t miss timing the tides so you can hike over a sand bar to isolated Bar Island before checking in to the classic Bar Harbor Grand Hotel.

Of course, the main attraction is Acadia National Park , with its breathtaking trails and views. Everyone can appreciate watching sunrise or sunset over Cadillac Mountain, and active visitors will enjoy renting a bike and exploring the car-free carriage trails throughout the park.

Rhode Island’s South Coast to Block Island, for New England seafood, surf and sunsets

Sunset on Block Island

By Jackie Gately at Enjoy Travel Life

“Little Rhody” has big things to offer in coastal road trips, with over 400 miles of beach-lined coast. A visit to the Newport Mansions and Cliff Walk are top regional attractions, but this off-beat coastal route from Wickford to Block Island is spectacular too.

Start in Wickford, a historic community in North Kingston known for its summer Art Festival.  You’ll find galleries, unique shops, and outdoor cafes throughout this quaint New England village on the harbor.

Take a beach break at Narragansett Beach, where the surf’s up!  Watch the surfers “hang ten,” or even take a surfing or paddleboard lesson.

Head south to Point Judith, famous for sourcing restaurateurs with delicious Point Judith Calamari. Enjoy Calamari or Portuguese Clams with Chorizo at George’s of Galilee, a clam shack overlooking Block Island Sound.

Board the high-speed Block Island Ferry at Galilee to catch a sunset over the Atlantic Ocean en route to Block Island. (You can leave your car behind and rent bikes on the  island.)

Browse the galleries and retail shops scattered in New Shoreham for souvenirs.

Pack a picnic lunch from Finn’s Seafood Restaurant, then spend the afternoon exploring Mohegan Bluffs, Settlers Rock, and the nature trails throughout Block Island. Or, just relax on one of Block Island’s 17 miles of pristine beaches before taking the ferry back.

Romantic getaways in New England

Connecticut – hartford to norwalk, a romantic new england road trip.

The Hartford, Connecticut skyline

Connecticut is full of happy surprises, and this short road trip is super accessible if you’re looking for a  romantic road trip.

Start by taking a stroll with your loved one in Elizabeth Park in Hartford. If you want to grab a good meal, Salute , Max Downtown , and The Capital Grille are among the best restaurants in Hartford.

Next, head south to Hubbard Park in the city of Meriden. Located in the Hanging Hills of Connecticut, this park comprises woodlands, streams, dramatic cliff faces, and flower gardens.

Turn on the radio and drive for a while, as the next destination, the Silver Sands State Park is in the city of Milford. Apart from the beach and the dunes, this park  has a 14-acre bird sanctuary.

You can also take a beach break at Calf Pasture Beach, which is just half an hour away from the Silver Sands State Park. Take pictures, stargaze, and plan future dates to make your day more romantic and memorable.

Also, Pinstripes Restaurant , about 10 minutes away from Calf Pasture Beach, serves some great Italian-American dishes!

Vermont – Stowe to Woodstock – Irresistable New England charm

The old, covered bridge in Woodstock, Vermont

Stowe and Woodstock have beautiful destinations that are perfect for a romantic getaway. Here are a few places you need to tick off on a road trip from Stowe to Woodstock.

The Moss Glen Falls on route 100 is a treat to the eyes. A short hike followed by a beautiful waterfall is a great way to start the day.

From Moss Glen Falls, continue on route 100 and turn left when you reach Interstate 89 to get to the next destination, the Brookfield Floating Bridge. It’s a small floating bridge where you can spend some quality time admiring the view with your partner. You can also go kayaking or swim there in the summar.

When you reach Woodstock, go to the Sugarbush Farm if you and your partner are fans of cheese and maple syrup. The cheese and maple syrup you get here are so delicious that you will probably take some home.

The Marsh-Billings-Rockefeller National Historical Park, just outside Woodstock, has beautiful sunflowers and a few hiking spots. You can also check out The Billings Farm and Museum nearby.

If you’re ready to go on a bit further, take route 4 and turn right to take route 7 to reach Baird Farm – Organic Vermont Maple Syrup at North Chittenden. It is an excellent maple farm that offers not only delicious maple syrups but also a stunning view.

Weekend getaways in New England

Sunset at Aquinas’s Gay Head Beach on Martha’s Vineyard

Martha’s Vineyard is an island in Massachusetts featuring cute towns, lighthouses, beaches, and farmlands. It’s ideal to spend two days here, one in Martha’s Vineyard, and explore the Outer Cape the next day.

To reach Martha’s Vineyard,  visitors usually take the ferry from from Woods Hole, in the town of Falmouth, on Cape Cod .

You can rent bikes and watch sunsets on the island. There are also many local restaurants that offer delicious food.

Stay at Martha’s Vineyard for the day, and tour the Falmouth area upon returning to the mainland.  The Nobska Lighthouse, The Knob, and Spohr Gardens are beautiful places to visit in Falmouth. The lighthouse and The Knob offer stunning views of the beach and the sunset.

You can also drive to Cape Cod Winery in East Falmouth for some delicious wine tasting! Also, remember to check out C Salt Wine Bar & Grille , which is one of the best restaurants in Falmouth.

Maine – Ogunquit to Portland – A relaxing getaway

Portland head light in Maine

If you are a fan of beaches, this road trip is for you. Start from Ogunquit, a quiet and relaxing beach town. The Marginal Way is where you can walk on a cliff that comes with beautiful coastal views and a lighthouse.

You can also visit the Ogunquit Playhouse theatre and the Ogunquit Museum of American Art in this beach town. The Front Porch Restaurant serves delicious food and has a festive piano bar upstairs.

On the way to the next destination, Kennebunk, you can stop by at a popular ice cream shop called Big Daddy’s, which is just 5 minutes drive from Kennebunk.

Kennebunk is home to the most fabulous Kennebunkport, where sites such as Gooch’s beach and Ocean Avenue top the list.

Once you are done swooning over how beautiful Kennebunk is, you can either continue on road 1 or Interstate 95 and then to the Interstate 295 to reach Portland City. If you have time, you can drive to Portland Lighthouse and take a stroll inside William’s Park.

Once you reach Portland, Fort Street Restaurant is a great place to have a delicious meal. You can also board a ferry to Peaks Island for some biking, kayaking, or swimming.

New England Road trip Essentials

Here’s a handy list of essential items for your road trip.

Don’t forget to pack these items:

• Fleece jacket – Handy for cool evenings by the ocean or at higher elevations.
• Cash – Some toll roads along the way may require cash.
• Nap Pillow – When it’s not your turn to drive.  This neck pillow is machine washable and compresses into a small bag.
• Extra Camera Memory Cards -With so much gorgeous scenery in New England,  you don’t want to miss a thing. I find the SanDisk cards are very reliable.
• A quick drying microfibre towel – So you’re always ready for impromptu visits to the beach and walks in the rain.
• Sunscreen and hand sanitizer – A must.
• Water Bottle – A reusable bottle to help stay hydrated while traveling.
• First Aid Kit – This kit has all the basics.

Stay safe and enjoy the beautiful scenery on your New England road trip!

Feel free to comment below with your recommendations.

More Information:

Tourism Information: Discover New England

Suggested Reading: Lonely Planet New England’s Best Road Trips , Fodor’s New England – Best Fall Foliage Drives and Scenic Road Trips

The Best Things to Do in Portland, Maine

15 Romantic Getaways in Upstate New York & Long Island

14 Fall Photography Tips for Awesome Autumn Images

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The best road trip stops and routes in New England

Lighthouses, historic brownstones, witchcraft, and more await you in this northwestern region

From cobblestone streets in historic Boston to the shores of Acadia National Park in Maine, New England offers a different landscape with each seasonal change. Spring is the perfect time to enjoy a baseball game; summer is ideal for beach combing; fall offers epic foliage; and winter is a skier’s paradise. So pack your bag according to the season and start planning your road trip to this coastal region.

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National park spotlight: Acadia National Park

As the only U.S. national park in the Northeast, Acadia offers stunning views, scenic drives, and pet-friendly trails.

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• Massachusetts
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7 Day New England Road Trip Itinerary: The Perfect Fall Getaway

This post may contain affiliate links, meaning if you buy or book through one of these links, I may earn a small commission .

Have you been dreaming of witch trials sites, fiery maple trees, and scenic rural drives? For fall lovers, one week exploring the vibrant foliage of New England is the ultimate bucket list experience. An adorer of autumn myself, I wrote the perfect 7 day New England road trip itinerary to fulfill your leaf peeping dreams.

This itinerary is inspired by my own road trip through New England last year, which included New Hampshire, Vermont, and Massachusetts. Although my home state of Ohio has gorgeous falls too and I’d already seen Massachusetts at peak coziness, I yearned to more deeply explore the hilly forests and farmland of the Northeastern United States. Sneaking in a lobster roll or two while revisiting Massachusetts wouldn’t hurt either!

New England’s compactness makes it easy navigate, while offering charming small towns, rewarding hiking trails, and coastal views. As this road trip covers three states, I’ve carefully planned this itinerary for the most efficient New England sightseeing route. Are you ready to get witchy in Salem, MA and cozy in Woodstock, VT? Let’s get into it.

Ultimate 7 Day New England Road Trip Itinerary

I have mapped out the below itinerary to further ease your navigation between these amazing New England destinations.

Related: 61 Awesome Bucket List Ideas for Your Best Fall Ever

Day 1: Massachusetts – Arrive Into Boston

This 7 day New England road trip itinerary kicks off in Boston, whose urban streets transform under autumn’s spell, particularly in the Beacon Hill neighborhood. If you are flying, you’ll land at Boston Logan International Airport, so grab a 10-minute Uber/Lyft into the city. Arriving either in the morning or the night before allows you to have a full day of sightseeing what they call “Beantown” .

The best thing to do during one day in Boston is to follow the Freedom Trail past sites significant to Boston’s Revolutionary War history. Either join a guided tour or simply follow the red line on the pavement from Boston Common. This self-guided app also provides an informative tour at your own pace.

Afterwards, stroll the boutiques and cobblestone streets of Beacon Hill or consume seasonal treats on the Underground Donut Tour .

Finish by dining at one of many Italian restaurants in Boston’s North End before turning in for the night. Don’t forget to stop in for a cannoli at Modern Pastry or a Boston cream donut at Bova .

Craving a spooky experience, but tired of walking? Take this Boston Ghosts and Gravestones Trolley Tour .

Suggested Stay: Courtyard by Marriott Boston Downtown/North Station

Day 2: Massachusetts – Salem, MA

No single 7 day New England itinerary would be complete without a visit to the Witch City, or Salem, MA, where the infamous 1692 witch trials took place. To make the 45-minute drive from Boston, pick up your rental car the morning of day two (we rented ours at the airport).

Note: If visiting during the super busy month of October, get into Salem by 9am to ensure you find parking and avoid traffic jams. An alternative is to stay in Boston for one more night and take a 30-minute train or ferry into Salem . I recommend booking a room at Courtyard by Marriott Boston Downtown/North Station to be close to both the train and Freedom Trail.

Here is the best way to spend one day (also consider following my Salem day trip itinerary ):

• Visit the Salem Witch Museum (purchase a timed entry ticket online)
• Stop into the Salem Witch House
• Stroll past the wand shops, fortune tellers, and apothecaries of Essex Street
• Take a spooky witch trials walking tour

For a nice dinner with lots of ambiance, dine at Ledger Restaurant . For less fuss and laid-back vibes, get a lobster roll and beer at The Lobster Shanty ; they serve delicious clam chowder too!

Suggested Stay: In Salem at the Hampton Inn Salem Boston or in Boston at the Courtyard by Marriott Boston Downtown/North Station

Related: 13 Best Things To Do In Salem , MA In October

Day 3: New Hampshire – Artist Bluff Trail

It’s time to get out of the city and into the White Mountains of New Hampshire, which deliver sweeping views over fall’s colorful tree canopies. On the morning of day three, depart from Massachusetts and drive about two hours north to Lincoln, New Hampshire. While there are plenty of hotels in and around Lincoln, you may opt to stay in a cozy cabin instead.

Recommended Hotel: Holiday Inn Express & Suites Lincoln East – White Mountains

You can find cabins all around the area, so I recommend doing a search on Airbnb and seeing what’s available during your travel dates. My husband and I stayed in this adorable dog friendly cabin in Wentworth, New Hampshire last year, where the stargazing looked like a sheet of glitter over the sky.

After settling in, it’s time for your first hike of the trip: the 1.5-mile Artist Bluff Trail in Franconia State Park. This steep loop trail leads to panoramic views over the fiery-colored treetops framing Echo Lake. For less climbing, take the Cannon Mountain Aerial Tramway just one mile away, which lifts you 4,080 feet to the peak of Cannon Mountain.

If you still have time and energy, also consider hiking the gorgeous two-mile Flume Gorge loop trail , which follows along an 800-foot natural gorge at the base of Mount Liberty. Just remember this trail has an entry fee of $18 online ( book here ) and $21 at the trailhead.

After hiking, visit a local brewery, like Rek-Lis Brewing Company , for dinner and drinks. As we were staying closer to Plymouth, NH, we stopped into Sole Track Brewing to share a tasting paddle. For dinner, we grabbed burgers at The Last Chair , a ski-themed brewery that had tasty burgers and peanut butter porter.

Day 4: New Hampshire – Kancamagus Highway

The next day in New Hampshire, you will experience the state’s most iconic leaf peeping adventure: the Kancamagus Highway . This 34.5-mile stretch of roadway between the towns of Lincoln and Conway leads past beautiful mountainscapes and other gorgeous natural scenery.

Keep in mind there are no gas stations along this route, so fill up before heading out. Also, you must pay $5 per day to park in White Mountain National Forest . You can simply put the cash or check in an envelope to leave at a drop box at the first stop along the highway.

Don’t be afraid to pull over frequently along the Kancamagus Highway. Otherwise, this enchanting stretch only takes about one hour to complete without stops.

Here are the must-see sights along the Kancamagus Highway, in order heading east:

• Otter Rocks
• Hancock Overlook
• Panoramic Overlooks
• Pemigewasset Overlook
• CL Graham Wangan Overlook
• Sugar Hill Scenic Vista
• Sabbaday Falls: Most popular hike along the way, only .5 mile trail that leads to a waterfall
• Russell-Colbath House
• Campney Fall: 3.1 miles out and back, .6 miles additional miles to reach the summit of Mount Chocorua, which has gorgeous 360-degree views
• Rocky Gorge: lovely in fall and nice place to picnic
• Lower Falls: this super short hike to a waterfall is the most popular stop of the drive
• Albany Covered Bridge

Stay overnight near Lincoln, NH again. If you are staying in a cabin, consider having a cookout or bonfire to make s’mores!

Otherwise, dine out at Moat Mountain Smokehouse and Brewery in North Conway before turning back to drive the Kancamagus Highway in reverse. You could also visit Woodstock Inn Brewery in North Woodstock upon completion of the drive.

Day 5: Vermont – Woodstock

The next morning, it’s time for the last leg of your trip: the friendly small towns of Vermont where even the automated speed signs scold you politely.

The drive to charming Woodstock (the one in Vermont, not New Hampshire) will only take about and hour and a half from Lincoln, NH. You could stay in a hotel in Woodstock or simply book an Airbnb in the surrounding area (we loved this adorable hobby farm ).

Recommended Hotel: The Village Inn of Woodstock

This route around Woodstock will be the delight of any 7 day New England road trip itinerary:

• Quechee Gorge: Visible from an overpass along Route 4, this 165-feet gorge (Vermont’s deepest) was formed by glaciers 13,000 year ago. You can park in a lot off Route 4 to quickly view the gorge or hike the Quechee Gorge Trail at Quechee State Park .
• The Skinny Pancake : A great breakfast/brunch stop in Quechee. I loved my savory crepe with apple, brie cheese, and a locally sourced blueberry compote.
• Woodstock: Explore the antique shops, cafes, and lovely covered bridges of this charming small town. Don’t forget that all parking is paid – even along the street!
• Billings Farm and Museum : For $17 you can explore the grounds and stables of this working farm tucked among the rolling hills. I purchased a small apple cider to sip as I strolled past dairy calls being milked, goats perched on top of fences, and horses grazing. Check their calendar for daily events.
• Woodstock Farmers Market: The perfect stop for locally produced products, like cheese and maple syrup.
• President Calvin Coolidge Historic Site : The site of several preserved buildings from Calvin Coolidge’s childhood home at Plymouth Notch, including his family homestead. Also see where the 30th president of the United States attended church, his father’s store, the post office, and Coolidge’s summer white house office inside of a dance hall.

Make a reservation to dine in downtown Woodstock at The Prince & The Pauper Restaurant or Santé .

Travel Savvy Tip

With the rise of social media, certain farms around the Woodstock area have become popular photo spots for Instagrammers. Sadly, this has escalated into a problem for local residents, with visitors clogging roads and trespassing onto private property.

Local governments have begun taking action, closing roads leading to Jenne Farm and Sleepy Hollow Farm during the month of October. Please respect these rules – there are plenty of other gorgeous locations all around Vermont to photograph!

Day 6: Vermont – Grafton

To get a true small town Vermont experience, drive one hour south of Woodstock to the tidy little village of Grafton. Grafton is especially pleasing during peak foliage season, when bright shades of red, orange, and yellow frame tall white church steeples and local shops.

However, don’t confuse Grafton’s impressive collection of well-preserved historic buildings for an open-air museum. This is a functioning, tight-knit community that still holds Gilmore-Girls-style town meetings to this day.

Just be sure to download any maps before heading out, as I found the town’s cell service to be weak to nonexistent.

Here are the best points of interest to check out in Grafton’s quaint and walkable town center:

• Learn about making maple syrup at Plummer’s Sugar House before buying some to take home with you.
• Hike a trail at the Grafton Trails & Outdoor Center . Grafton also has a cute welcome sign a bit further south down Grafton Road.
• Journey to the past at the Grafton Historical Society.
• Sample local cheese varieties at the Grafton Village Cheese Company .
• Browse locally produced gifts and home goods at Mercantile and adjacent Dover House Antiques.
• Wander into the Turner Hill Interpretive Center to learn the story of Alec Turner, who settled in Grafton and to raise his family after escaping slavery.
• Check out the Nature Museum to learn about native New England flora and fauna and wander down various nature trails.
• Discover unique copper sculptures honoring Northeastern Native Americans at Jud Hartman Gallery .

If you get hungry, the Grafton Village Store has you covered for coffee, pastries, and simple meals. For a sit-down dinner, book a reservation at the rustic Phelps Barn Pub or the cozier 1801 Tavern at The Grafton Inn .

Day 7: Complete Your New England Road Trip Itinerary at Boston Logan Airport

Just as the leaves must eventually fall to the ground, this New England road trip itinerary must reach its end too. Hopefully you had the fall foliage experience you’ve been dreaming about and are already planning your return trip!

If you drove from your house, then it’s time to make the trek back home. Otherwise, the drive from Woodstock, Vermont to Boston Logon International Airport will take about two and a half hours. I recommend arriving two to three hours before your flight to have time to drop off your rental car, check any bags, and find your gate.

Is Your New England Road Trip Itinerary Longer Than 7 Days?

There are so many options for New England itinerary add-on’s:

• Consider spending one extra day in Boston.
• Stay in Salem, MA for two days and day trip to nearby Danvers (formerly Salem Village) to see even more witch trials sites!
• Explore additional charming towns along the Vermont and New Hampshire border, including White River Junction, Windsor, Hanover, and Battlebro.
• Add an extra day to New Hampshire to take advantage of countless more hiking trails.
• Add an additional state: Maine! Explore trendy Portland, eat lobster rolls in Bar Harbor, or go hiking at Acadia National Park .

There you have it – the recipe for a dreamy and memorable 7 day road trip itinerary through New England. It’s the best combination of the bustling Atlantic coast of Massachusetts, the mountains of New Hampshire, and the farms of Vermont. You’ll see exactly why New England is beloved by leaf peepers, maple syrup addicts, and outdoor lovers alike!

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The perfect New England fall-foliage road trip for 2023

Oct 2, 2023 • 7 min read

On this 424-mile drive through New England, the foliage will dazzle © Chun Chen / 500px / Getty Images

Touring New England in search of autumn’s changing colors has become so popular it has grenerated its own subculture of “leaf-peepers.”

While admiring the leaves during foliage season is possible everywhere in the the region, here’s one road trip that will immerse you in the best of those glorious colors.

New England’s best fall-foliage road trip

Trip length : 5– 7 days; 424 miles (682km) Best time to go : Late September to mid-October Essential photo : Kent Falls set against a backdrop of autumnal colors Top experience : Zip-lining through the tree canopy in Bretton Woods

Scarlet and sugar maples, ashes, birches, beeches, dogwoods, tulip trees, oaks and sassafras all contribute to the carnival of autumn color in New England. But this trip is about much more than just flora and fauna: expect to embrace the harvest spirit makes at family outings at pick-your-own farms, leisurely walks along dappled trails and tables groaning beneath delicious seasonal produce.

1. Lake Candlewood, Connecticut 

With a surface area of 8.4 sq miles, Candlewood is the largest lake in  Connecticut . On its western shore,  Squantz Pond State Park is popular with leaf-peepers who come to amble along the pretty shoreline. In Brookfield and Sherman, quiet vineyards with acres of gnarled grapevines line the hillsides; at  White Silo Farm Winery , the focus is on specialty wines made from farm-grown fruit. For the ultimate bird’s-eye view of the foliage, consider a late afternoon hot-air balloon ride with GONE Ballooning  in nearby Southbury.

The drive: From Danbury at the southern tip of the lake, you have a choice of heading north via US 7, taking in Brookfield and New Milford (or trailing the scenic eastern shoreline along Candlewood Lake Rd S); or heading north along CT 37 and CT 39 via New Fairfield, Squantz Pond and Sherman, before reconnecting with US 7 to Kent.

2. Kent,  Connecticut

Picturesque Kent ranks among the top spots for fall foliage in all of New England. Situated in the Litchfield Hills on the banks of the Housatonic River, the village is surrounded by dense woodlands. For a sweeping view, hike up Cobble Mountain in Macedonia Brook State Park , a wooded oasis two miles north of town. The steep climb to the rocky ridge affords panoramic views of the foliage against a backdrop of the Taconic and Catskill mountain ranges.

The 2175-mile (3500km) Georgia-to-Maine  Appalachian National Scenic Trail  also runs through Kent and up to Salisbury, on the Massachusetts  border. Unlike much of the trail, the Kent section offers a mostly flat five-mile walk alongside the Housatonic, the longest river walk of the entire trail. The trailhead is accessed on River Rd, off CT 341.

The drive:  The 15-mile drive from Kent to Housatonic Meadows State Park along US 7 is one of the most scenic drives in Connecticut. The single-lane road dips and weaves between thick forests, past Kent Falls State Park  (with its tumbling waterfall, visible from the road) and over West Cornwall’s picturesque covered bridge, which spans the Housatonic.

3. Housatonic Meadows State Park, Connecticut

During the spring thaw, the churning waters of the Housatonic challenge kayakers and canoers. By summer, the scenic waterway transforms into a lazy, flat river perfect for fly-fishing. In the Housatonic Meadows State Park, campers vie for a spot on the banks of the river while hikers take to the hills on the Appalachian Trail. Housatonic River Outfitters runs guided fishing trips with gourmet picnics.

Popular with artists and photographers, one of the most photographed fall spots is the Cornwall Bridge (West Cornwall), an antique span that stretches across the broad river, framed by vibrantly colored foliage.

The drive:  Continue north along US 7 toward the Massachusetts border and Great Barrington. After a few miles, you’ll leave the forested slopes of the park behind you and enter expansive rolling countryside dotted with large red-and-white barns. Look out for hand-painted signs advertising farm produce – and consider stopping overnight in Falls Village, which has an excellent B&B.

4. The Berkshires,  Massachusetts

Blanketing the westernmost part of Massachusetts, the rounded mountains of the Berkshires turn crimson and gold as early as mid-September. The effective capital of the Berkshires is Great Barrington, a formerly industrial town whose streets are now lined with art galleries and upscale restaurants.

It’s the perfect place to pack your picnic or rest your legs before or after a hike in the nearby Beartown State Forest . Crisscrossing its 12,000 acres, hiking trails yield spectacular views of wooded hillsides and pretty Benedict Pond. Further north, October Mountain State Forest is the state’s largest tract of green space (16,127 acres), also with ample hiking trails. The name – attributed to Herman Melville – gives a good indication of when this park is at its loveliest, with its multicolored tapestry of hemlocks, birches and oaks.

The drive:  Drive north on US 7, the spine of the Berkshires, cruising through Great Barrington and Stockbridge. In Lee, the highway merges with scenic US 20, from where you can access October Mtn. Continue 16 miles north through Lenox and Pittsfield to Lanesborough. Turn right on N Main St and follow the signs to the park entrance.

5. Mt Greylock State Forest,  Massachusetts

Massachusetts’ highest peak is not so high (only 3491ft / 1064m) – yet a climb up the 92ft-high War Veterans Memorial Tower rewards you with a forested panorama stretching up to 100 miles across the Taconic, Housatonic and Catskill ranges and over five states. Even if the weather seems drab, driving up to the summit may well lift you above the gray blanket, and the view with a layer of cloud floating between tree line and sky is simply magical.

Mt Greylock State Reservation has some 45 miles of hiking trails, including a portion of the Appalachian Trail. Frequent trail pull-offs on the road up – including some that lead to waterfalls – make it easy to get at least a little hiking in before reaching the summit.

The drive:  Return to US 7 and continue north through the quintessential college town of Williamstown. Cross the Vermont border and continue north through the historic village of Bennington. Just north of Bennington, turn left on Rte 7A and continue north to Manchester.

6. Manchester, Vermont

Stylish Manchester is known for its charming architecture. For fall-foliage views, head south of the center to 3828ft-high  Mt Equinox , the highest mountain accessible by car in the Taconic Range. Wind up the 5.2 miles – with gasp-inducing scenery at every hairpin turn – seemingly to the top of the world, where the 360-degree panorama unfolds, offering views of the Adirondacks , the lush Battenkill Valley and even Montréal ’s Mt Royal . 

If early snow makes Mt Equinox inaccessible, visit 412-acre Hildene , a Georgian Revival mansion once home to the Lincoln family. It’s filled with presidential memorabilia and sits nestled at the edge of the Green Mountains, with access to eight miles of wooded walking trails.

The drive:  Take US 7 north to Burlington. Three miles past Middlebury in New Haven, stop off at Lincoln Peak Vineyard for wine tasting or a picnic lunch on the wraparound porch.

7. Lake Champlain, Vermont

With a surface area of 490 sq miles and straddling  New York , Vermont and  Québec , Lake Champlain is the largest freshwater lake in the US after the  Great Lakes . On its northeastern side, Burlington is a gorgeous base from which enjoy the lake. Explore the lively city by foot, then scoot down to the wooden waterfront promenade, take a swing on the four-person rocking benches and consider a bike ride along the 7.5-mile lakeside path.

For the best off-shore foliage views, we love the  Friend Ship sailboat at  Whistling Man Schooner Company , a 43ft-sloop that accommodates a mere 13 passengers. Next door, ECHO Lake Aquarium & Science Center explores the history and ecosystem of the lake, including a famous snapshot of Champ, Lake Champlain’s mythical sea creature.

The drive:  Take I-89 southeast to Montpelier, passing  Camels Hump State Park and  CC Putnam State Forest . At Montpelier, pick up US 2 heading east to St Johnsbury, where you can hop on I-91 south to I-93 south. Just after Littleton, take US 302 east to Bretton Woods.

8. Bretton Woods, New Hampshire

Unbuckle your seat belts and step away from the car. You’re not just peeping at leaves today: you’ll be swooping past them on zip lines that drop 1000ft at 30mph. The four-season Bretton Woods Canopy Tour includes a hike through the woods, a stroll over sky bridges and a swoosh down 10 cables to tree platforms.

If this leaves you craving even higher views, cross US 302 and drive six miles on Base Rd to the coal-burning, steam-powered Mount Washington Cog Railway  at the western base of Mt Washington , the highest peak in New England. This historic railway has been hauling sightseers to the mountain’s 6288ft (1916m) summit since 1869.

The drive:  Continue driving east on US 302, a route that parallels the Saco River and the Conway Scenic Railroad, traversing Crawford Notch State Park . At the junction of NH 16 and US 302, continue east on US 302 into North Conway.

9. North Conway, New Hampshire

Many of the best restaurants, pubs and inns in North Conway come with expansive views of the nearby mountains, making it an ideal place to wrap up a fall-foliage road trip. If you’re traveling with kids or skipped the cog railway ride up Mt Washington, consider an excursion on the antique Valley Train with the Conway Scenic Railroad , a short but sweet round-trip ride through the Mt Washington Valley from North Conway to Conway, 11 miles south. The Moat Mountains and the Saco River will be your scenic backdrop. First-class seats are usually in a restored Pullman observation car.

This article was first published September 2019 and updated October 2023

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5+ Amazing road trips in New England: Scenic drives you’ll love

The beautiful northwestern region of the United States makes the perfect place for a road trip and there are so many different routes you can take to get the best of each season.

From chasing the best fall colors to mesmerizing coastal drives, national parks, and cities. New England has it all. In this post, travel bloggers share their favorite road trips in New England to inspire your own adventure.

So get ready to explore some of the best places in New England !

Disclosure: This post may contain affiliate links. That means that if you make a purchase through one of those links, I will get a small commission at no extra cost to you. As an Amazon Associate, I earn from qualifying purchases.

Table of Contents

What to prepare for a road trip in New England

To make sure you get the most successful road trip in New England you need to be well prepared. Not only do you need to make sure you have a big enough car, but if you travel with children or pets, you need to make sure they have everything they need to assure a comfortable trip for everyone.

Will you be camping or staying in hotels along the way? Will you be doing any outdoors activities you need to pack for? Here are the main things to think about before you head off.

Before you head off for a New England road trip, you need to make sure you have an adequate car. Make sure you have a car that is big enough for the people that are going including all the luggage. If you travel with dogs, you need to think about space for them too.

When driving for several hours in a row, it’s crucial to be comfortable, so enough space for everyone in the car is a must. You can check out different rental cars to fit your need here .

Travel insurance

Travel insurance is essential whenever you go on a road trip through New England. Make sure you’re covered for your needs. If you go hiking, diving, or do other adventure activities during your trip, you need to assure that your travel insurance covers it.

World Nomads is my go-to for travel insurance. They are super easy to understand and you can buy what you need in only a few moments. The good thing with World Nomads is that you can add only the coverage you actually need.

Cover your camera gear, electronics, and adventure activities during your trip in an instance here .

While World Nomads is easy it’s also a responsible travel insurance company giving back to local communities through its Footprint Program. You can choose to give a micro donation when you buy travel insurance that will go to the project you choose.

Buy World Nomads travel insurance HERE .

Accommodation

When you plan your New England road trip itinerary, you need to decide what kind of accommodation you want to stay in during your trip.

If you prefer staying in high-end hotels it’s a good idea to book it upfront so you make sure you find one that suits your needs and can plan your overnight stops accordingly.

Some rural places might only have B&B’s or campgrounds to stay at. If you like car camping, then you might want to spend the night in different destinations. You can also read my complete camping packing list here .

No matter what your thing is, make sure you check for accommodation so you don’t get stranded sleeping in your car, especially in high season.

You can search for and book accommodation here .

If you plan on camping, make sure you check out the best pop up tents here and the best tents for camping with dogs here .

You might also like: Best weekend trips from Boston

Best road trips in New England

Now, let’s check out some amazing New England road trips for your next vacation.

Recommended by Karen Warren of Outdoor Adventure Sampler

• Length of the road trip: 332 km/206 mi
• Start and endpoint: Brattleboro to South Hero Island
• Recommended number of days: 2-3 days
• Best time of year: Fall

For a New England road trip full of cultural experiences and astounding natural beauty, driving through Vermont is an incredible option. With its world-famous foliage, fall is definitely the best season for a road trip through Vermont and makes for one of the best road trips in the US .

Starting in Brattleboro, drive up Route 30 to see the West Dummerston Covered Bridge, one of over 100 covered bridges in Vermont. Continuing north on scenic Route 100, drive through picturesque villages with no stoplights in the heart of the Green Mountains.

Stop at any general store to get a dose of Vermont culture with your coffee. Don’t miss the Vermont Country Store in Weston for a dose of Americana and unique travel gifts .

The charming village of Stowe is worth a visit. A destination for skiers in the winter, Stowe is also lovely in the fall with foliage colors ablaze on the surrounding mountains. The gondola ride gives marvelous views of Mt. Mansfield, the highest peak in Vermont.

As you leave Stowe, make sure to stop at Ben & Jerry’s in Waterbury for a tasting and tour of Vermont’s most famous ice cream.

The next stop is vibrant Burlington, the largest city on your Vermont road trip. Grab a maple creme and stroll the walkways along Lake Champlain for views of the Adirondack Mountains across the water. 

Be sure you stay overnight here so you can watch the best sunset in New England and then catch the nightlife on pedestrian-friendly Church Street. The Hilton Burlington has rooms with a view of Lake Champlain.

Finish your trip with a drive through the bucolic  Champlain Islands .  Search for the roadside miniature stone castles of South Hero Island. Visit one of the apple orchards or the Snow Farm Vineyard and Winery for a taste of local agrotourism. Stay at the Crescent Bay Farm Bed & Breakfast, a restored 1820’s farmhouse.

READ: Best waterfall hikes in Brevard NC

Kancamagus Highway

Recommended by Jamie Andreson of Travel Addict

• Length of the road trip: 60 km/36 mi
• Start and endpoint: Conway, NH to Lincoln, NH
• Recommended number of days: 1 – 2 Days
• Best time of year: Autumn: last week of September or first two weeks of October

The Kancamagus Highway is a beautiful scenic drive that makes one of the best fall foliage drives in New England. While it’s prettiest in autumn during the  fall foliage peak in New Hampshire , it can be visited during any season of the year. It’s a fantastic experience in New Hampshire for all of its rural beauty.

You find some of the most beautiful East Coast hiking locations , viewpoints, and picnic spots along the route that are worth stopping at. There are also a few traditional covered bridges worth viewing and visiting on the route as well.

One of the hikes not to miss is the Moat Mountain Trail, located near Conway. It is roughly 10 miles long and leads past Diana’s Baths.

Another fantastic hike is Sawyer Pond Trail, located near Lincoln, it’s a shorter route of 3 miles to Sawyer Pond on a densely forested, and shaded path.

The Albany Covered Bridge is one of the few covered bridges near the Kancamagus Highway. It’s located towards the Lincoln side of the route and right next to the Boulder Loop Trailhead, another great hike, and with two local campgrounds nearby.

There are no hotels along the route, but plenty at either end (Lincoln or Conway). There are plenty of campgrounds along the route though, for those who fancy a bit of a rustic trip.

Acadia National Park

Recommended by Neha from Travelmelodies 

• Length of the road trip: 27 mi/43,5 km (Park Loop Road)
• Start and endpoint: Loop from Hulls Cove Visitor Center
• Recommended number of days: 1-2 days
• Best time of year: Spring to Fall with summer being the busiest

Acadia National Park in the state of Maine is one of the sought-after national parks on the East Coast for its diverse landscape.

A road trip across this 47,000-acre wide area by the Atlantic Coast gives you an opportunity to experience the rugged coastline, beautiful lighthouse, and mountain with magnificent vistas that will leave you mesmerized. And for sure to come back again for more. 

The best way to explore the area is by driving the 27-mile Park Loop Road beginning near the Hulls Cove Visitor Center. The road traverses through diverse terrain and making it a memorable drive.

There are multiple scenic spots on the route that are worth stopping and enjoying the beauty like Thunder Hole, Sand Beach, Otter Cliff, and many more. Jordon Pond in the park is another attraction that is a must-visit.

There is no better place to eat except the Jordan House restaurant with mesmerizing views of the Jordon Pond and delectable food.

If adventure attracts you then, there are many scenic hikes that take you through some untouched parts of the park.

One of them is to the summit of Cadillac Mountain. It is the highest point in the national park that offers some scintillating views of the waters and the flora and fauna around. Cadillac Mountain is also accessible by road and is worth visiting in the dawn for views of the sunrise.  

Bass Harbor Lighthouse is not on the Park Loop Road but is one of the most photographed lighthouses. 

There is an entrance fee to avail the pass to Acadia National Park which is valid for 7 days of purchase. There are campgrounds inside the national park that need to be booked well in advance.

But if campgrounds are not the choice then the town of Bar Harbor is the best place to stay. Bar Harbor Inn & Spa is one of the  best places to stay near Acadia National Park .

Fall Foliage Route

Recommended by Jenny of Limitless Hiker

• Length of the road trip: 400 mi/644 km
• Start and endpoint: Start in Maine and finish in Vermont
• Recommended number of days: 1-2 weeks
• Best time of year: Last week of September to the first few weeks of October

New England is a must visit destination in the fall . Since fall colors change North to South, it’s best to start as far North as you can. Every year fall comes at a different time.

To maximize your New England road trip itinerary, it’s best to be flexible so you can adjust accordingly to the leaves changing. Local tourism boards will update their websites with information on the status of the leaves.

It’s best to plan this trip from the last week of September, through the first few weeks of October.

To really be able to capture the full essence of fall on this trip, one to two weeks is recommended.

Start in Maine and explore Acadia National Park. You can drive through the park, or get out and hike as much as you want. Explore all of the nearby lighthouses, before heading to New Hampshire.

Stop by Dixville Notch State Park in New Hampshire. There are fall foliage photo opportunities everywhere! From there head to the White Mountains and drive along Kancamagus Highway, which is 37 miles through the White Mountains.

There are stops and hiking trails along the entire drive that take you through some of the most beautiful fall foliage in New England.

From New Hampshire, head to Vermont, which looks like it was taken right out of a storybook.

Woodstock, VT is full of photogenic farms to take photos of. Plus you can support some of the local farms by grabbing some maple syrup!

Woodstock is also a cute town to explore in itself. There are several restaurants and shops to enjoy wandering through.

Boston to Portland

Recommended by Tegan and Alex of Why Not Walk

• Length of road trip: 112 miles (180 kilometers)
• Start and end point: Starting in Boston, ending in Portland, Maine
• Recommended number of days: 4-5 days
• Best time of year: All year round

For an ideal mix of New England’s best coastal cities and towns, consider a road trip beginning in Boston, Massachusetts and ending in Portland, Maine.

This trip is very easy to do, as it hardly strays from Interstate-95, but is also highly customizable, allowing you to plan stops and brief detours along the way to explore some of New England’s most quintessential towns. 

Be sure to stop in Salem, Massachusetts to learn about the history of the Salem Witch Trials, as well as in Plymouth to visit the infamous Plymouth Rock.

Nearby, Gloucester, Newburyport, and Rockport have adorable town squares and ample opportunities to gaze at the rocky outcroppings that make New England beaches so renowned.

Rockport in particular is home to Motif #1, the most-painted building in America.

Not too far away, the town of Ipswich is known as “America’s best-preserved Puritan town”. Mainly due to its fabulous period architecture dating all the way back to the 17th century. But also the Crane Estate is a great example of the opulence of post-Industrial Revolution summer homes.

Continuing north, stop in Portsmouth, New Hampshire for more architectural splendor and perhaps some tax-free shopping, as well as many boutique hotels to stay for the night. A particular favorite is the centrally-located Ale House Inn . 

Portsmouth is located right on the border with Kittery, Maine, also an outlet-shopping haven, as well as very close to the gorgeous beach communities of York, Ogunquit, and Old Orchard Beach.

If you’re seeking lighthouses, don’t miss Maine’s unparalleled variety, perhaps stopping at the Cape Neddick Lighthouse in York and of course, the Portland Head Light in Cape Elizabeth, Maine’s oldest lighthouse, prior to arriving in Portland.

While in Portland, be sure to check out the Old Port area, as well as walking around Commercial Street.

READ: Best day trips from Boston

Boston to Hanover

Recommended by Nicole Hunter of Go Far Grow Close

• Length of the road trip: 200 km/126 mi
• Start and endpoint: Boston to Hanover
• Recommended number of days: 5 days
• Best time of year: Late spring and early fall

A road trip that captures the beauty of New England is the one between Boston, Massachusetts and Hanover, New Hampshire.

You will get to experience Boston, a large city with lots of history, food, and shopping, and then Hanover, a charming small College town with a Main street and all the lovely restaurants and shops that it has to offer. 

Boston is a fantastic walking city. There are lots of amazing hotels in downtown Boston, including the Hyatt Regency which is ideally situated so you can explore the Freedom Trail – a 2.5 mile walk that connects 16 historically significant sites – or take a food tour of Little Italy or the Boston Public Market. 

The drive between Boston and Hanover is relatively flat and mostly through forests and rolling hills. If you want to experience the outdoors, for camping and hiking, make sure you stop at Bear Brook State Park and Mt. Kearsarge State Forest Park. Lake Sunapee is wonderful for relaxation but also swimming, kayaking, or paddleboarding.

Hanover is another lovely walking town right on the border of Vermont. One of the best places to stay is at the Hanover Inn, right across from Dartmouth College and at the start of Main Street. Dartmouth College offers daily tours to explore the beautiful historical buildings.

If you are feeling particularly active, you can access the Appalachian trail and go for a beautiful hike. If you go in the spring or fall, don’t forget to bring a packable rain jacket in case it rains .

On the other hand, if you are in love with Ben & Jerry’s Ice Cream, you can take a day trip to its factory in Waterbury, Vermont and take a delicious tour.

IF YOU HAVEN’T GOT A RENTAL CAR YET, MAKE SURE YOU

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Reflections on these New England road trips

There are so many amazing options for road trips in New England and no matter what you opt for it will be a wonderful experience. From mesmerizing New England scenic drives to towns and cities where you can spend days exploring, this corner of the US is absolutely worthwhile for your next driving vacation. I definitely know I’ve got a few new ideas for my bucket list!

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10 Best Summer Road Trips in New England

Dreaming of a New England road trip? From back roads and small towns to coastal spots, these are the best summer road trips in New England.

By Tracey Minkin

Jul 07 2022

Get ready for a summer road trip!

Rangeley Lakes Scenic Byway Maine

Mount Desert Island Loop Acadia National Park, Maine

Coastal Crossing New Hampshire

Green mountain ribbon vermont, alpine drama vermont.

Mohawk Trail Massachusetts

Housatonic valley connecticut, the quiet corner connecticut.

Shore of Dreams Rhode Island

Kingly cape cod massachusetts, see more: 10 prettiest coastal towns in new england the 25 best beach towns in new england 10 best seaside inns in new england.

New England Wanderlust

Connecticut , Maine , Massachusetts , New Hampshire , Rhode Island , Vermont  ·  March 28, 2024

31 Best Places To Visit In New England In 2024

Planning a trip to the northeast and wondering what the best places to visit in New England are? Well, I’m happy to say you’ve come to the right place 😊 I live locally in the northeast, and have been exploring the New England region for over 15 years now. I’ve been all over this area, scouting out the most beautiful towns, finding the most exciting cities, have taken tons of road trips, and set sail to visit the islands off the coast. And this post is a compilation of my absolute favorite places in New England that I’ve visited over the years that I think are worth your time.

Ready to explore this beautiful region with me? Great! I’m happy to show you around 😊 Under each destination, I’ll share why I love it, and what I think are the top things to do.

On this list, you’ll find a mix of popular places you’ve likely heard of because well, they’re popular for a very good reason! And then I’ve also included some off-the-beaten-path gems that you may not have come across that I think are so beautiful.

So with that, let’s get started!

New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our  Privacy Policy .

Best Places To Visit In New England

1. mount desert island & acadia national park.

Acadia National Park always tops everyone’s list of things to see in New England, and as someone who’s been there tons of times, I can say that it lives up to its reputation. This is where you’ll find that postcard-worthy, dramatic coastline Maine is famous for, so if you’re looking for the most iconic views in the state, Acadia is very much worth your time.

Acadia is located on Mount Desert Island, which is actually home to a lot of other beautiful places in New England to see, including the closest town to the park – Bar Harbor. This charming little coastal town is where most people stay when visiting the park, and it’s a worthy destination on its own.

On Mount Desert Island, you’ll also find Southwest Harbor, Tremont, and Somesville, all of which have their own fun things to do, and gorgeous scenery to enjoy.

Inside the park, I recommend driving Park Loop Road, walking Ocean Path for the best views for the the least amount of effort, having lunch at Jordan Pond House, enjoying sunrise (or sunset!) at the top of Cadillac Mountain, and taking on a few hikes (Great Head, Beehive, Gorham, and Bubble Rock are some of my favorites.

Psst! I have some guides on visiting Acadia and Bar Harbor, which go into more detail on how to plan your trip, including:

• My Perfect Acadia National Park Itinerary
• Visiting Bar Harbor In The Winter

2. Whale Watching In Stellwagen Bank National Marine Sanctuary

Did you know that New England is home to some of the best whale watching in the world? Yep, that’s right! Off the coast of this region is the Stellwagen Bank National Marine Sanctuary , which is known for its very active marine life, including different kinds of whales ranging from humpback to minke. In fact, it’s quite common to have a humpback sighting in this region, so make sure to have your camera ready 😉

And what’s even better is that you can hop on a whale watch tour that heads out to Stellwagen from a few different places around New England. My favorite is Dolphin Fleet , which sails out of Provincetown on Cape Cod, MA. Another great option is Cape Anne Whale Watch , which departs from Gloucester, MA.

3. The Cape Cod National Seashore

Cape Cod is known as one of the best places for a beach vacation in New England, and while a lot of that has to do with the charming coastal towns, amazing seafood, and beautiful scenery, I think it’s a special place because of the Cape Cod National Seashore.

This area on Cape Cod is so picturesque and undeveloped, that it was designated as protected land by President John F. Kennedy in 1961. It’s home to some of the most beautiful beaches in New England, lighthouses, scenic trails, and lots more. In fact, this is the top thing I suggest to everyone visiting Cape Cod.

Within the national seashore, my favorite things to do are walk the Nauset Marsh trail to Coast Guard Beach (my favorite beach on Cape Cod), see Nauset Lighthouse, and hike out to Race Point Lighthouse.

Psst! I have a detailed guide all about the 6 Cape Cod National Seashore beaches , including a breakdown of each one, and my tips on which you should visit on your trip.

4. The Brewster Flats, Cape Cod

Most people haven’t heard of the Brewster Flats on Cape Cod, but they’re actually the largest tidal flats in North America! And honestly, it’s such a cool thing to experience, and definitely one of the most beautiful experiences to have in New England.

So, what does that mean, exactly? Well, every day at low tide, the tide goes so far out that you can walk on the ocean floor for about a mile. Not only does it feel like you’re at the end of the world, it’s great for spotting marine wildlife and getting a first-hand look at what lives at the bottom of the ocean floor in this region.

The Brewster Flats, despite their name, expand further past the town of Brewster along the Cape Cod Bay side of the peninsula, and you can find them at beaches between Dennis and Eastham.

5. Provincetown, MA

I’ve already mentioned Provincetown as a great launching point for a whale watch tour, but it’s such a cool destination on its own that it’s very much worth its own spot on this list.

Provincetown is located at the very trip of the Cape Cod peninsula, and honestly, there’s no other place quite like it. It’s both a lively and peaceful beach town, packed with character, and you’ll find picturesque scenery at every turn.

Provincetown has long been known as a haven for artists and the LGBTQI+ community, and the welcoming nature of the town can be felt once you arrive. The main street that runs through town is called Commercial Street, and it’s filled with art galleries, independent shops, restaurants, and cabaret clubs. And honestly, everyone is always in such a good mood while here! I have to spend time in Provincetown every time I visit Cape Cod, and it’s almost indescribable, so definitely go experience it for yourself 😊

6. Chatham, MA

Known as the most idyllic and charming town on Cape Cod, Chatham is also one you don’t want to miss while visiting the region. Home to a lovely Main Street with great shopping and dining, the side streets are filled with gorgeous houses, and perfectly manicured gardens bursting with hydrangeas in the summer.

In Chatham, you’ll also have beaches to explore, a lighthouse to see, and this is also one of the best places to spot seals on Cape Cod . The Chatham Fish Pier and Market is where many of the local fisherman dock, and well … the seals know what’s on those boats 😂 So, they hang out there waiting for some treats, and they get so close to the pier, allowing you to enjoy their cuteness up close.

Psst! I have lots of guides about Cape Cod, and here are some of my most popular ones:

• Best Towns To Stay In On Cape Cod
• Visiting Cape Cod For The First Time: Must-See Things, And My Top Tips
• The Best Time To Visit Cape Cod & The Islands
• Unique Things To Do On Cape Cod
• Scenic Walking & Hiking Trails That I Love On Cape Cod

7. Nantucket, MA

As one of my all-time favorite places in New England to visit, Nantucket is one I always recommend to people looking for one of the most idyllic places in the country. This island off the coast of Cape Cod is just so charming that it’ll be tough to not snap pictures of it your entire visit.

Once you step off the ferry and onto the cobblestoned streets of downtown, you’re greeted with storefronts covered in traditional Cape Cod shingles, and you’ll start to wonder if you’ve been transported into a Hallmark movie.

But in additional to the gorgeous downtown area, Nantucket is also home to some of the best beaches on the East Coast, as well as charming rose-covered cottages, beautiful lighthouses, and impressive hydrangeas in the summer.

Nantucket is one of the most expensive destinations on this list, and unfortunately, hotel prices can be prohibitive for a lot of people. However, spring and fall offers some savings, and day trips are always a great way to experience the island (and are easy to do from Cape Cod).

I have a few guides about visiting Nantucket if you need more information, including:

• Ultimate Nantucket Day Trip Guide
• How To See Nantucket’s Lighthouses
• Cape Cod vs. Nantucket: Which Is Best For You?

8. Aquinnah Cliffs – Martha’s Vineyard

The other Cape Cod island is no less special, and a bit different than Nantucket in some ways – but also very beautiful! One of the best places to visit in New England is absolutely Martha’s Vineyard, and one of the pretties places on the island to experience is the Aquinnah Cliffs.

The famous Aquinnah Cliffs offer dramatic coastline views with towering bluffs and a beautiful lighthouse. The beach below the cliffs, Moshup Beach, is also open to the public, and includes a short scenic trail that leads down to the shoreline, making the entire experience worth the effort to get to this part of the island.

But that isn’t the only reason Martha’s Vineyard is worth visiting. It’s also known for its gorgeous gingerbread cottages in Oak Bluffs, the stunning South Beach, lovely lighthouses, charming towns, Jaws Bridge (yep, from the movie!), and amazing rural scenery (and as a result, awesome farm stands!).

I have a few guides about visiting Martha’s Vineyard if you need more information, including:

• Best Things To Do On Martha’s Vineyard
• How To See Martha’s Vineyard Without A Car
• Best Beaches On Martha’s Vineyard
• Ultimate Martha’s Vineyard Day Trip Guide

9. Newport, RI

Heading over to Rhode Island, Newport is definitely a destination to have on your radar as you plan your trip to New England.

This “City by the Sea,” as it’s often called, doesn’t really feel like a city at all, and more like a charming town on the water. Known for its Gilded Age mansions, incredible culinary scene, beautiful scenery, amazing coastal walks and drives, and awesome shopping, there’s something to do here for just about anyone.

Of course, The Breakers mansion is one thing you don’t want to miss during your visit. This mansion serves as a “summer cottage” for the Vanderbilt family, and the entire state is just one impressive, opulent room after another, including a gorgeous veranda overlooking the ocean.

During your trip, I also recommend doing the Cliff Walk, which a pedestrain path along the coast that offers some of the best views in Newport. And if you have time after exploring downtown, definitely cruise along Ocean drive for more coastal views.

Psst! I have a detailed guide on planning a Newport, RI day trip , which includes top things to do!

10. Block Island, RI

Off the coast of Narragansett in Rhode Island is the beautiful little Block Island. This is one that can often get over-shadowed by Nantucket and Martha’s Vineyard, but I really love exploring this little island.

The island is very small, which makes it easy to see in a day, or offers a relaxing vacation if you have more time to spend here. Built around the main town that has cute shops and dining options, you’ll also find beautiful beaches that are free to visit, great hiking trails, lots of gorgeous coastal scenery, awesome sunsets, lighthouses, and even the Block Island National Wildlife Refuge .

My favorite places to see on the island are the Clay Head Trail, Mansion Beach, lunch at The Oar overlooking the water, the Mohegan Bluffs, and North Lighthouse.

Psst! I have a detailed guide on taking a Block Island day trip , if you’re looking for more information 😉

11. Westerly & Watch Hill, RI

Lastly for Rhode Island, it’s hard to not include Westerly and its village of Watch Hill on this list. While it’s one of the most expensive and exclusive places to visit along New England’s coast, it makes for a gorgeous vacation if you have the budget for one of the hotels in the area. Or, even a fun day trip!

I this this is where you’ll find the best beaches in Rhode Island outside of Block Island, and combine that with cute downtowns and luxury hotels, and you’ve got a recipe for a wonderful New England beach vacation. In fact, Taylor Swift loved it so much, she bought a mansion in Watch Hill, so I’m definitely not the only one who loves it here!

My favorite beaches in Westerly are Misquamicut State Beach, which is the easier one to visit, and Napatree Point in Watch Hill, which has more limited parking. And if your budget allows, definitely book a room at the famous Ocean House resort in Watch Hill, which has its own private beach, incredible rooms, and is home to one of the world’s best waterfront restaurants, as chosen by CNN Traveler .

I also recommend you visit both downtowns in Watch Hill and Westerly, and head over to Grey Sail Brewing for a unique atmosphere and local craft beers.

Psst! I have a detailed guide on the best things to do in Westerly and Watch Hill, RI , if you’re looking for more ideas 😉

12. Boston, MA

New England’s largest city is also one of the top places to visit when exploring the area, and for so many wonderful reasons: the history, the charming character, beautiful parks, waterfront scenery, amazing hotels, and incredible food are just a few!

Even though I’m not a big city person, it’s hard to deny what an amazing destination Boston is, and the best part is that it feels very New England . There’s lots of historic architecture to enjoy, and the quaint neighborhoods with cobblestone streets just add to the ambience.

During your visit, I highly recommend visiting the Public Gardens (which were the first in the U.S.!), walking around Beacon Hill (my favorite neighborhood), exploring the Freedom Trail, walking the Charles River Esplanade, and making reservations at some of the top-rated restaurants.

I have a few guides all about Boston, including:

• Boston In The Fall
• Best Boston Food Tours
• Best Boston Hotels Near The Aquarium

13. Rockport, MA

Heading north of Boston, the next few places will all be located along the Massachusetts North Shore, which is one of my favorite places in New England to visit. And the charming fishing town of Rockport is one you should have on your radar.

Rockport is small, but what it lacks in size, it makes up with picturesque and unique scenery. Home to Motif 1, which many say is the most painted building in the country (some say the world), this red fishing shack stands guard over the town in the harbor, and is one of the most idyllic New England moments to photograph.

Along the harbor, you’ll find Bearskin Neck, which sounds a bit alarming 😂, but it’s really just a street where you’ll find the colorful storefronts and art galleries – all of which are independently owned, and feature all kinds of unique finds.

Outside of the main town area, you can also admire the town’s impressive rock quarry landscapes, and one of the best places to do that is at Halibut Point State Park.

Psst! I have a detailed guide on the best things to do in Rockport, MA , if you’re looking for more ideas 😉

14. Crane Estate & Crane Beach, MA

There are quite a few mansions and castles around New England, and the Crane Estate is one of my absolute favorites. Located along the North Shore in Ipswich, this Tutor-revival mansion was built in 1928, and sits on 2,100 acres of beautifully manicured lawns.

The grounds and mansion are open to the public, and most people choose to visit the grounds to explore the beautiful gardens, and the walking trails around the property. However, the interior of the mansion is open for guided tours at certain times throughout the year, too, but it does require the purchase of a separate ticket.

In addition to the immensely impressive grounds, the Crane estate is also home to Crane Beach, which I think is the most beautiful beach on the North Shore. This 4-mile long sandy beach seems to stretch on forever, and there are also over 5 miles of scenic trails to enjoy here.

15. Newburyport, MA

A lesser-visited destination along the North Shore is Newburyport, and here, you’ll find an incredibly charming downtown, beaches and parks on Plum Island, and some of the best shopping in New England. When I first visited Newburyport, I immediately fell in love with it, and I’m so surprised more people don’t recommend visiting.

The town center of Newburyport sits along the Merrimack River, and you’ll find a beautiful waterfront park where you can enjoy the views. From there, you’re steps away from town center and all the incredible shops, most of which are independently owned. I always describe the scenery as a movie set, because everything from the brick-lined streets to the beautiful window displays at the shops just feels so cozy and charming.

From Newburyport, you can also head out on a whale watch to Stellwagan Bank (although, sometimes from here, they cruise out to Jeffreys Ledge, depending on what the experts think is the best option that day).

Psst! I have a detailed guide on the best things to do in Newburyport, MA , if you’re looking for more ideas 😉

16. Salem, MA

Known as one of the top Halloween towns in the entire U.S., Salem is undoubtedly a popular fall destination in New England, and rightfully so. With its Haunted Happenings event that takes place all throughout October, as well as being home to several Hocus Pocus filming locations, and it’s very haunted past, it checks all the boxes for a perfect fall getaway.

However, Salem is incredible year-round, too! While the witch trial attractions and haunted tours are definitely worthy of your time, the towns is also filled with gorgeous and historic New England architecture, picturesque streets, fantastic museums, lighthouses, and tons of charm.

One off-the-beaten-path location in Salem I love to share with people is Winter Island Park, which has a cute little lighthouse and some trails to enjoy. During your visit, be sure to also see the House of Seven Gables, where Nathaniel Hawthorne was born (and where he pulled inspiration from when he wrote the book of the same name!), explore the Peabody Essex Museum, and enjoy the views from the Salem Maritime National Historic Site.

Oh, and if you can squeeze in a lobster martini from the Lobster Shanty, I definitely recommend that, too 😉

Psst! I have some extra guides on Salem, including the best time to visit Salem, MA , and how to plan a day trip to Salem!

17. The Berkshires, MA

Located in the northwest corner of the state, The Berkshires is a region comprised of 30 towns, mountain ranges, and beautiful rural scenery. It’s also home to fantastic museums, amazing dining options, cozy inns, and endless outdoor activities, making this a wonderful region to see on your trip to connect with nature. I especially love it in the fall season to enjoy all the incredible foliage color.

One of the most famous towns in The Berkshires is Stockbridge, which was put on the map when artist Normal Rockwell painted his Stockbridge Main Street at Christmas piece. And while a few things have changed since then, most of Main Street feels very much the same, so you can feel as though you’re stepping into a real-life painting!

Some of my favorite things to do in this region are drive the auto road (or hike! I’ve done both) to the top of Mount Greylock, drive the scenic Mohawk Trail, visit the incredible farm stands, explore the beautiful Naumkeag Estate (which often puts on seasonal events like a pumpkin display in the fall), and meander through the charming towns like Lenox and Great Barrington.

18. Kennebunkport, ME

Moving into Maine, Kennebunkport is one of the best places in New England to visit to enjoy picturesque coastal scenery, beaches, and a charming downtown. Kennebunkport has long been a big vacation spot for New Englanders, but President Bush made it even more famous with his summer vacation house and compound, which is still there for you to admire from a distance.

I’ve been to Kennebunkport more times than I can count, and it just never disappoints. Built around Dock Square, the main part of town, you’ll find colorful store fronts, idyllic waterfront scenery, and beautiful side streets filled with traditional colonial houses.

If you venture a bit outside of town center, you’ll find the beautiful beaches, as well as a scenic, coastal walking trail called Parsons Way. There’s also the option to visit Cape Porpoise, which is packed with postcard-worthy moments at every turn, as well as one of the best places to get a lobster dinner – Langsford Road Lobster & Fish House.

One of the best part of Kennebunkport, too, is that it had tons of fantastic hotel options, including historic colonial homes-turned-cozy-inns, luxury resorts, cottages, beach resorts, and upscale escapes in the woods.

19. Ogunquit, ME

Very close to Kennebunkport is another fantastic coastal town – Ogunquit. This town is known for having one of the best beaches in Maine, but it’s also home to a very charming downtown and gorgeous scenery. My very first visit to Ogunquit made me fall immediately in love with it, and because it offers so much to do, it’s definitely one of the best places to visit in New England.

The star of the show here is definitely the beach, and one of the best features of the beach is that it’s walkable for most places in town. Since Ogunquit is rather small, it makes getting around on foot very easy, and therefore, offers a truly relaxing vacation.

My absolute favorite thing to do in Ogunquit, and even all of New England, is the Marginal Way pedestrian coastal walk. This path hugs the coastline and stretches for over a mile one-way, and connects Ogunquit town center with a cute little harbor called Perkins Cove. I also love to meander through the shops downtown, visit the art galleries, and spend most of my time at the gorgeous beach.

Psst! I have a detailed guide on visiting Ogunquit, Maine , if you’re looking for more information 😉

20. Lubec, ME

Located in the northeastern most corner of Maine, Lubec is such an underrated destination in New England. This small, authentic fishing village is just minutes from the Canadian border, and offers incredible hiking and nature trails, an awesome lighthouse, beautiful coastal scenery, and easy access to Campobello Island, where you can find President Franklin Roosevelt Eleanor’s summer home (as well as a lighthouse and some beaches).

Now, Lubec isn’t for everyone. The town is very small, and there’s not a ton to do, but it’s one of my favorite places in New England to visit to get away from everyday life, and not plan to do a whole lot. That said, I find it incredibly charming, and I always get excited to visit.

My favorite things to do here are visit West Quoddy Head State Park to see the lighthouse, tackle the scenic coastal trails, visit the brewery, and take afternoon excursions to Campobello Island.

Psst! I have an entire guide on visiting Lubec, Maine , if you’re looking for more info and tips 😉

21. Boothbay Harbor, ME

Along Maine’s Midcoast region is the wonderful town of Boothbay Harbor, and as the name suggests, it’s built around a beautiful harbor, making this an idea destination to enjoy the rugged coastline Maine is known for.

Boothbay Harbor is also very small, so the downtown is entirely walkable, making it an idea place for a relaxing getaway. And the colorful storefronts that line the streets add to its charm. Both sides of the harbor are connected by a footbridge, which just makes it even more picturesque here.

I always love to recommend that you get out on the water as much as you can when you visit Boothbay to enjoy the surrounding natural beauty, and there are tons of wonderful tours you can take here, including puffin tours, sailing cruises, and lighthouse excursions.

Lastly, Boothbay Harbor is minutes away from the Coastal Maine Botanical Gardens, which is such a treat to visit.

Psst! I have an entire guide on the best things to do in Boothbay Harbor, Maine , if you need more ideas!

22. Camden, ME

Also along Maine’s Midcoast is gorgeous Camden, and this town almost always ranks at the top of every list of the best places to visit in New England, and the hype is justified. Much like Boothbay Harbor, Camden is built around the harbor, creating an idyllic coastal escape, and you’ll find a wonderful downtown with great shops and restaurants, cozy places to stay, and opportunities for amazing sailing tours.

Nearby is also Camden Hills State Park, and one of the best things to do is drive up the auto road, or hike to the top of Mount Battie, and enjoy a birds-eye view of the harbor.

23. Portland, ME

Portland is another one of my favorites cities in New England, and much of that has to do with the lighthouses. In fact, it’s home to one of the most photographed lighthouses in the northeast – Portland Head Lighthouse. Located in South Portland, just a few minutes from downtown, you’ll find this incredible lighthouse park with trails that offer different viewpoints of the lighthouse, and stunning, dramatic coastline to admire.

Nearby are also two smaller lighthouses that are worth visiting – Spring Point Ledge Light, and Bug Light.

That said, Portland is so much more than its lighthouses. Once an old port city (as the name suggests!), part of the city has maintained its charm and authenticity, and you’ll find lots of fishing boats and lobster traps down picturesque alleyways in the Old Port district.

But Portland is also an incredible culinary destination, and there are so many up and coming chefs and restaurants making named for themselves here, too. Taking a food tour is a great way to introduce yourself to the city, and don’t forget to get some of the famous donuts, too!

24. St. George Peninsula, ME

An under-the-radar destination in Maine, the St. George peninsula is a stunningly beautiful area of the state. While it does have one famous landmark, Marshall Point Lighthouse, many people overlook the rest of it, but it’s actually a wonderful place for a getaway, and to explore.

And of course, Marshall Point Lighthouse is one of the top things to see! Located at the very end of the peninsula, the lighthouse was featured in the movie Forrest Gump, and it’s one of my favorites in the region.

Driving around the area, you’ll see fishing boats bobbing in the water backdropped by pine-tree covered islands, quaint seafood shacks, and quiet town centers. But if you’re looking for more things to do, Rockland and Camden are just a short drive away, as is the beautiful Owls Head State Park and lighthouse.

25. The White Mountains In New Hampshire

One of the absolute best places to visit in New England for fall foliage is the White Mountains region, but because of it’s impressive scenery, it really is wonderful year-round. Home to the White Mountains National Forest, incredible hiking, fun attractions, and cute little towns, it’s easy to see why so many people visit each year. It’s also where you can find New England’s highest peak – Mount Washington.

During your visit, you’ll definitely want to cruise along the Kancamagus Highway, which is known as being one of the most scenic drives in New England – and I couldn’t agree more. This is especially beautiful in the fall, but the road goes through the heart of the White Mountains forest, making the views during the drive memorable.

Some other wonderful things to do in the area are visit the cute town of Littleton, hike the Artist Bluff Trail, visit Flume Gorge, ride the Cannon Mountain Aerial Tramway, and also take a ride on The Cog to the top of Mount Washington for an incredibly unique experience.

26. Portsmouth, NH

In southern New Hampshire, Portsmouth is one of the most charming places to see in New England. While the White Mountains have more of a cabin/alpine atmosphere, the New England charm is alive and well in Portsmouth!

This coastal city also feels more like a quaint town, and most of it is very walkable. Streets are lined with traditional New England colonial architecture, the downtown area is filled with amazing shops and picturesque streets, and there are tons of wonderful restaurants to choose from.

I like to start my trips to Portsmouth with a walk along the waterfront at Prescott Park, and be sure to head over to Pierce Island for awesome views of the city. Then, walk over to the Strawbery Banke museum to see history come to life (open seasonally), and admire all the historic houses. Finally, head over to Market Square downtown, where you’ll find all the shops and restaurants, and be sure to pick up a cup of coffee and a pastry from Elephantine Bakery in Commercial Alley!

27. Woodstock, VT

It’s continually named the prettiest town in Vermont, and I have to agree. Woodstock is where you want to go in Vermont to feel like you’re in a Hallmark movie because it has all the ingredients: a town green, covered bridges, independent shops, idyllic side streets, and cozy places to eat. It really all does live up to the hype.

On the outskirts of town, you’ll also find postcard-worthy rural landscapes, as well as the gorgeous Billings Farm & Museum, and Sugarbush Farms.

Psst! I have an entire guide on the best things to do in Woodstock, VT , if you need more ideas!

28. Stowe, VT

A very close second when it comes to my favorite places in Vermont is Stowe, which is known as being a top town for fall foliage and skiing in the winter. This is one of the most popular places to visit in Vermont, but I really do think it’s worth braving the crowds for because the scenery really is that beautiful.

Stowe is home to Vermont’s highest peak, Mount Mansfield, and is also surrounded by mountain ranges. In the fall during peak foliage season, seeing them dripping in autumnal color is really something special.

But the actual town itself is incredibly charming, and you’ll find covered bridges, a quaint Main Street with great shops and country stores, scenic walking trails, and awesome hiking and nature walks nearby at Smugglers Notch.

Psst! I have an entire guide on the best things to do in Stowe, VT if you need more information!

29. Lake Willoughby, Vermont

An under-the-radar destination in Vermont in Lake Willoughby, which offers incredible scenery of the surrounding mountains, and is another impressive fall foliage destination. Located in the North East Kingdom of the state, the actual lake itself is gorgeous, and stretched for over 2 square miles.

For a quiet getaway in Vermont, it’s really hart to beat. The main town along the lake, Westmore, offers tons of cabins to rent for a relaxing vacation, and the area also has awesome hiking nearby in Willoughby State Forest that offers fantastic views of the lake and surrounding mountains.

But even if you visit just for the day, the drive around the lake is really amazing, and there are some fun places to eat nearby, including The Gap Pub and the Parker Pie Company.

30. Mystic, CT

Heading into Connecticut, Mystic is such a wonderful place to visit in New England! Most people know it from movies like Mystic Pizza and Mystic River , but it has so much to offer, making it worthy destination to experience when you visit the area.

Built around the actual Mystic River, the small town offers beautiful waterfront scenery as you explore. It’s also home to a charming Main Street for shopping and dining, and a cute little shopping village called Olde Mistick Village, where you can find all kinds of unique stores and tons of charm.

Some of the bigger attractions in Mystic, like the Mystic Seaport Museum and the Mystic Aquarium, add to the appeal, too. In fact, the Mystic Seaport Museum is the largest maritimes museum in the U.S., and is mostly an outdoor exhibit along the river. It features historic tall ships that you can climb onto before walking through an authentic New England maritimes village from the 19th century.

Driving a bit outside of town, you can also visit part of the Connecticut wine trail in Stonington, which includes Saltwater Farm Vineyard, and Stonington Vineyard.

Psst! I have an entire guide on the best things to do in Mystic, CT , if you need more ideas!

31. Litchfield Hills, CT

Last on my list is perfect for any Gilmore Girls fans out there because it’s the region that Amy Sherman-Palladino based Stars Hollow on. But even if you have no idea what I’m talking about, the Litchfield Hills region of the Connecticut countryside is filled with idyllic rural scenery, beautiful drives, state parks, and lots of quaint and charming towns.

Towns in this region like Kent, Litchfield, and New Milford all feel like they could have inspired Stars Hollow, but many claim the beloved TV show town was modeled after Washington Depot (which oddly enough, isn’t my favorite town in the region!). You’ll find cozy cafés, bookshops, town greens with gazebos, and lovely scenery at every turn.

This region is also small and can easily be visited in a weekend, and if you’re ambitious, a day. The drive along from one town to the next is scenic, and with stops to make on the way at Kent Falls State Park, Lover’s Leap Bridge, and Mount Tom, it’s not hard to see why someone would have based an entire show on this area.

Visiting New England FAQ

Is New England Worth Visiting?

As I’m sure you’ve gathered from this list, there are so many incredibly picturesque places to see in New England, which very much makes it worth visiting.

Between exciting cities, historic towns, quaint fishing villages, lighthouses, and charming destinations, there’s truly something for everyone, and there’s a reason why this region is a bucket list place for lots of people.

What’s The Best Way To Get Around New England?

Unless you just plan to visit a big city, you really need to have a car to explore New England.

I wish the U.S. in general had a better transportation infrastructure, but it just doesn’t, and New England is no exception. Getting to a lot of these places requires a car, but this will allow you the most freedom to stick to your own schedule.

What’s The Best Airport To Fly Into In New England?

Boston Logan is the best airport for most people, especially if you’re flying in internationally. This airport is the biggest in New England, and most often offers the cheapest flights, most options, and is centrally-located to most destinations in the region.

There are some smaller airports around New England that may work best for you, including Portland, Providence, and Portsmouth. However, Boston Logan is usually the best option.

What’s The Best Season To Visit New England?

The great thing about New England is that all four seasons offer a different vibe, so this really depends on what kind of trip you’re hoping for. Here’s a very general breakdown for you:

→ The first two weeks of October for fall foliage.

→ July and August for a coastal or beach trip (but this is peak season for these areas, so prices and crowds will be at their highest). This is when you’ll get the best weather, and all seasonal businesses along the coast will be open.

→ June and September for shoulder season along the coast. You’ll experience fewer crowds, but the weather is generally still very nice.

→ May is a great option if you’re looking for a cheaper and less crowded time to visit, and don’t mind weather that’s a bit rainy.

→ January and February for a winter wonderland or ski vacation.

I do have a very detailed post on the best time to visit New England , if you’re looking for more info 😉

Is New England Expensive?

Unfortunately, yes. This area tends to be more expensive than many other parts of the U.S., so expect to pay a bit more for everything, including hotels, tours, and food. “Budget-friendly” will also likely run a bit more than average, too. However, you can still cut costs by staying in motels with efficiency kitchens to prepare your own meals, camping, etc.

Planning A New England Road Trip

Oh boy, do I have some great suggestions for you! I’ve done a lot of road trips around this region, and continue to do them because it’s one of my favorite ways to explore. My favorites I’ve ever done are a Boston to Bar Harbor, Maine road trip, as well as a beautiful fall foliage road trip.

I’ve created a few different road trip itineraries for this website, which you can find here:

• My Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary
• My 7 Day New England Road Trip Itinerary
• My Perfect New England Fall Foliage Road Trip Itinerary
• My Epic Maine Lighthouse Road Trip Itinerary

My Top Tips For Visiting New England

→ Know that weather can change … a lot 😂 New England is known for moody weather, and while it’s not quite as bad as places like Iceland or Scotland, it does change a lot. July and August are known as the driest months, but rain is still likely at least a few days of each summer month. And the spring and fall season can being a wide variety of weather, so definitely check the forecast a few days before your trip.

→ The highways have paid tolls . If you’re planning a road trip, or even a longer drive to a different location, it’s good to know you’ll have to pay tolls on many of the highways. However, they’ve all recently switched over to electronic, contactless tolling. If you’re renting a car, or from out of state, you’ll get a bill in the mail to pay, so you don’t need to worry about stopping to pay tolls each time.

→ Expect a lot of crowds and book well in advance if you visit during peak season . Hotels and tours fill up months in advance if you plan a visit during a peak time, so you’ll want to book as soon as you can. For example, the first two weeks in October in New Hampshire, Vermont and The Berkshires, or in July and August on Cape Cod.

→ You can dress casually for the most part . Despite its reputation for being preppy, most people dress very casually in New England. Unless you plan to go out to eat at a nicer, upscale places, you don’t really need to dress up.

→ Have some cash on you, depending on where you go . Most places will take cards, but a surprising number of smaller seafood shacks and ice cream places will still be cash only. Many will have an ATM on-site if that’s the case, but to avoid pricey fees, it’s good to just have some cash on you.

More posts you may find helpful:

• Best Day Trips In New England
• Incredible New England Resorts & Spas
• Gorgeous New England Islands Worth Visiting
• Must-See Towns On The New England Coast
• Best Beach Towns In New England
• Ultimate Guide To Fall In New England

That’s A Wrap On The Best Places To Visit In New England

And there you have it! My guide to all the best places to visit in New England, including some of my helpful tips and suggestions on things to do. I hope you’ve found this helpful as you begin to plan your trip. Whether you’re excited to explore all the most epic fall foliage spots in the region, drive up the coast of Maine, or take a road trip around the entire region, one thing’s for sure – all of the places mentioned in this post will provide you with incredible memories along the way. Happy planning!

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10 Routes That Make For The Perfect New England Road Trip

Cross through valleys and marvel at gorgeous lakes in the best road-tripping routes that New England has to offer.

With imposing mountain ranges on one side, and a beautiful coastline that overlooks the Atlantic Ocean , the New England region definitely has to be on anyone's bucket list when it comes to wanting a versatile road trip that could be as short as cruising along Connecticut, to as lengthy as following all the way along the region's coastal landmarks .

Whatever the case may be, some of the most famous United States road trip routes can be found in New England, serving as relaxing pathways and being a great way of showcasing both the land's natural beauty and the charming towns along the way .

10 Olympic Trail Scenic Byway

Starting off strong, and entering from the east side of New York, the Olympic Trail Scenic Byway begins with a first-hand view of the majestic Lake Ontario and ends at the Vermont side of Lake Champlain.

• The trail gets its name due to going straight through the historic village of Lake Placid , which is known for having hosted the Winter Olympic Games several times in the 20th century.

The whole length will be met by cozy mountainous villages, towns, and peaceful lakes to stop by and turn a trip into an adventure. And, if that wasn't enough, the whole route has the Adirondack Mountains follow along in the distance for the perfect landscape in the background of each picture taken.

• Length: 170 miles
• Route: Sackets Harbor → Keeseville

There's a much shorter version of the trail that connects Keeseville with Lake Placid.

9 Maine's Coastal Tour

Maine's coastline is a long and beautiful stretch of land that perfectly meets with the ocean for amazing views every second of the way.

The whole road can be either taken in small sections or just going from one point to another and turning into a several-day vacation that takes the best from the most picturesque side of Maine .

• Length: 272 miles
• Route: Kennebunkport → Bar Harbor

Related: Discover The Charm Of New England: 10 Essential Stops On The New York City To Boston Route

8 Vermont Route 100

Out of all the states that make the region of New England, Vermont has got to be the most stunning when it comes to natural landscapes comprised of huge forests, beautiful lakes, and picturesque mountains throughout the whole state.

Route 100 makes for a drive that goes from one end of Vermont to the other, going through all sorts of highlights like magical roadside castles and amazing views of the Green Mountains basically from start to finish.

• Length: 217 miles
• Route: Moss Glen Falls → Stamford

Related: Exploring The Beauty Of The Florida Keys On A Road Trip Along The Overseas Highway

7 Kancamagus Scenic Byway

Making for a totally surreal experience to be lived during fall, the Kancamagus Scenic Byway consists of a much shorter drive that can still be considered a perfect New England road trip.

Filled with the aesthetic beauty and rich history of New Hampshire, the route has been designated an American Scenic Byway, with the main highlights of the trip being the luscious forest pathways inside the White Mountain National Forest and first-hand encounters with clear rivers and waterfalls.

• Length: 34.5 miles
• Route: Bath → Conway

6 Mohawk Scenic Byway

As a route that showcases Massachusetts' history, culture, and natural beauty, the Mohawk Scenic Byway joins the Connecticut River Valley with the historical venues of the Berkshire Mountains .

The route goes through what once was a footpath used by Native Americans, well before it was turned into the state’s first designated scenic auto touring road, and along historic villages to make for great attractions that serve as marvelous breaks between driving.

• Length: 69 miles
• Route: Connecticut River Valley → Berkshire Mountains

5 Old King's Highway

Following along historic route 6A, Old King's Highway is famous for being both the oldest road leading to Cape Cod and for having been a massive part of the region's history, serving as a trail for Native Americans to pass by and later becoming a cart path for farmers to transport their produce.

Nowadays, it's used as a scenic driveway along the coastline of Massachusetts for a short road trip or to get to one of the many beautiful beaches .

• Length: 58 miles
• Route: Sandwich → Cape Cod

4 Park Loop Road

Passing right through Acadia National Park on Mount Desert Island , Park Loop Road takes visitors on a 3-hour-long trip through the park's most scenic route and most popular attractions to be found, such as the Heart of Acadia, Cadillac Mountain, and Jordan Pond.

However, due to being such a popular route, there's bound to be a lot of traffic, especially during peak travel seasons such as summer and fall, so be prepared to share the road with plenty of people.

• Length: 27 miles
• Route: Paradise Hill Road → Sand Beach

Related: Road Trip Rules: 10 Towns You Need To Visit On Route 93

3 Skiers Paradise

As a much shorter alternative to experience the snowy side of Vermont, this route goes by what's known as Skiers Paradise , a set of mountains, slopes, and wonderful ski resorts perfect for daredevil tourists .

It's not necessary to go up the mountains to fully appreciate the landscape, though, as being able to ride across this snow wonderland is more than enough to make for an unforgettable road trip.

• Length: 80 miles
• Route: Stowe → Woodstock

2 Bold Coast Scenic Byway

Also turning a much longer route into a more manageable drive, the Bold Coast Scenic Byway goes through 125 miles of Maine's coastline from the southeast region and passes by the bordering area of Acadia National Park for amazing views throughout the whole way.

What makes this one of the best road trips in New England, is that it also celebrates the Bold Coast way of life by going through the most prolific fishing villages for a chance to taste some of the best seafood in the country .

• Length: 125 miles
• Route: Milbridge → Eastport

1 Rural Connecticut

For a more quaint and peaceful drive along farms and meadows, why not travel across the rural side of Connecticut? Sure, it might be much flatter and quieter than every other route on the list, but that's exactly what makes it stand out.

Just pass by farmsteads and peaceful towns as the wind slowly blows on the fields.

• Length: 40 miles
• Route: Old Norwich → Woodstock

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Perfect New England Fall Road Trip: 10, 5, 3 Day Itinerary 2024

May 31, 2023

Your Influencer Coach & Fellow Content Creator

I'm a travel creator and influencer coach based out of Arizona. This blog is where I share the best itineraries for US & beyond, 63 US National Parks , and influencer tips . Read More About Me ⟶

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What do fiery oranges, sultry yellows, candy-apple reds, quaint cabins, and Gilmore Girl towns all have in common? New England in the fall.

The best way to experience all that and more is with a New England fall road trip itinerary.

So in this post, we’re going to spill all the tea (or pumpkin spice?) on how to pull off the best NE itinerary including information I’ve gathered from three separate New England fall trips I’ve taken over the years.

We’ll cover multiple itineraries: 10 days, 5 days, and 3 days—mainly focused on Vermont, New Hampshire, and Maine (maps included).

To start, we need to cover some must-know planning details before you embark on your trip!

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Disclaimer: Hey, pumpkin spice lover! This blog contains affiliate links which means I earn a v small percentage of every purchase at no additional cost to you. These affiliate links help support me and my blog, but there is absolutely no pressure to use them!

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Planning Your New England Fall Road Trip

Let’s start with a quick peep at some planning 101’s.

Where is New England📍 — New England is a compilation of US states: Maine, New Hampshire, Vermont, Massachusetts, Connecticut, and Rhode Island.

States with the Best Foliage🍁 — New Hampshire, Maine, Vermont—all covered in this post.

When to Go❓ — Late September, Mid-October—First week of October is usually a good ballpark.

Trip Length⏰ — 10 days is ideal—5 to 7 is great too (all covered in this post)

Fly✈️ — Start in Boston or Albany, New York. Check KAYAK for flights starting at $53.

Rental Car🚗 — Also check KAYAK for the best prices in Albany or Boston !

Now, we need to dive into my top “need to knows” for planning your trip.

When is the Best Time to See Fall Colors in New England in 2024?

The best time to see fall colors in New England is beginning to mid-October.

After three years of experience, I have always had the best luck exploring the first week of October.

The peak time to see colors can change depending on how much water the trees receive leading up to the fall season. A dry season can result in less vibrant leaves!

Insider Tip: As you plan, keep a daily eye on the New England peak fall foliage map —which leads us to the next must-know.

Fall Colors Are (Semi) Unpredictable

Planning fall trips to New England can be a tricky business. You see, you’re playing with a season, and seasons can be unpredictable. 

My advice: be as flexible as possible with your New England fall trips.

Daily, you’ll want to keep an eye on the leaf monitors to ensure you’re getting the most accurate reading of colors.

During my trips, I found that sometimes the leaves would change color overnight! 

Insider Tip: Don’t get tied up in going to a single spot for New England fall foliage. Instead, have a general list of places you want to see and go from there. This blog will provide you with plenty of options!

Choosing Your Starting Point

From experience, starting your New England fall road trip itinerary in Albany, NY or Boston, MA (Boston-Logan International) will give you the best flexibility and EPIC itineraries .

My favorite trips have always been a loop, beginning in NY, heading North, and ending in New York’s Adirondacks .

I want to make sure you have options, though.

So first, we’ll cover a 10-day itinerary from Albany, NY. Then as a bonus, we’ll cover starting from Boston (in case you want to do that instead).

Let’s start with the Albany itinerary.

Insider Tip: Leaves tend to change north first and gradually work their way south. When in doubt, hit your northern fall foliage destinations first and move down! 

10-Day New England Fall Road Trip Itinerary Starting in New York

• Day 1 — Arrive in Albany, NY ; Berkshires
• Day 2 — White Mountains ; Kancamagus Highway
• Day 3 — Franconia Notch State Park
• Day 4 — Crawford Notch State Park
• Day 5 — Acadia National Park
• Day 6 — Acadia National Park
• Day 7 — Dixville Notch State Park
• Day 8 — Stowe, VT ; Smuggler’s Notch
• Day 9 — Lake Placid, NY ; Adirondacks
• Day 10 — Head to Albany, NY

Below is a map that includes all the destinations I listed for the ten-day New England fall road trip and the bonus locations we’ll cover later. 

The map has layers for our alternative itineraries (coverd later), recommended things to do, and places to eat we’ll cover in this post!

Click here for a live version of the map!

You can thank me later ;).

Let’s dive in! Each day has its own list of things to do, places to eat, and where to stay.

Day 1 — Berkshires, MA

Day 1 in Sum (Total Drive Time: ~2 hours)

• Morning: Arrive in New York and pick up car
• Afternoon: Drive to Berkshires, ~2hrs
• Evening: Visit Mount Greylock
• Stay: Tourists , The Williams Inn

Now let’s look at the details!

After flying into New York and picking up your car , your New England foliage adventure will begin in the Berkshires, MA. 

I suggest arriving to Albany the evening before day one OR early to late afternoon on day 1 .

This way, you have enough time to drive to the Berkshires and explore the area.

Insider Tip: I love this itinerary so much because starting in Albany allows you to explore the NY Adirondacks too (we discuss this in the post)!

Your drive to the Berkshires from Albany, NY, will be about 1 hour and 20 minutes—it’s a great place to start the fall fun!

Start by heading to Mount Greylock, the highest peak in Massachusetts, which stands at 3,489ft.

Don’t worry; I’m not making you hike the very first day you get here.

Drive up to the top of Mount Greylock and admire the fall views from above!

For food in the area, Korean Garden is the place for tasty Asian dishes!

Another option is Pera Bistro which offers a Mediterranean menu.

Insider Tip: To and from Mount Greylock, you’ll have stores like Walmart available in case you need supplies and snacks!

Where to Stay Near The Berkshires

Adams and Williamstown are where you’ll find amazing mountain resorts tucked away in the woods—perfect for fall.

Here’s a quick list of places you’d like:

Tourists ($$$) — Luxury accommodations that will make you think you’ve just entered the mountain escape of your dreams. Pet friendly, great food, great music, even BETTER vibes.

The Williams Inn ($$$) — Luxury hotel nestled in the mountains that will make you feel like east coast royalty. Great for couples with spacious, clean rooms and super cozy beds—check out the bar and The Log restaurant!

If camping is more your vibe, you’ll be a bit out of the way, but the Savoy Mountain State Forest has options for tent camping, car camping, and log cabins.

You must reserve a spot ahead of time, though before choosing to camp here during your fall road trip in New England.

Insider Tip: Tomorrow will be one of the longer driving days because you’ll want to head to the White Mountains from here, so rest up!

Day 2 — White Mountains, New Hampshire

Day 2 in Sum (Total Drive Time: ~5 hours)

• Morning: Drive the Mohawk Trail Scenic Drive
• Afternoon: Drive to White Mountains, New Hampshire
• Late Afternoon: Explore Kancamagus Highway
• Stay: The Stonehurst Manor , Ledge & Lake Chalet , North Conway Grand Hotel

If day one didn’t satisfy your hunger for pumpkin spice and fall vibes, day two will!

Drive the Mohawk Trail

Before leaving Massachusetts, you’ll drive the Mohawk Trail —one of the most scenic New England foliage drives! 

The entire trail stretches about 69 miles.

The drive includes plenty of mountainside vistas that’ll make you fall in love with MA—see what I did there ;).

Insider Tip: Make sure you bring something like a Sony a6400 and 24-70mm f/2.8 lens for some pictures!

Lincoln, NH

After 4 hours, you’ll arrive in Lincoln, NH — a town in New Hampshire’s White Mountains and a well-known hub for visitors.

Once there, grab something to eat at Gypsy Cafe or a coffee at Half Baked & Fully Brewed ( The Moon Cafe & Bakery is a great alternative)!

Alternative: None of that your vibe? Black Mtn Burger Co is another popular place to eat in Lincoln, NH!

Explore the Kancamagus Highway

Today, you’ll explore some popular attractions along the Kancamagus Highway !

Driving the entire Kancamagus Highway takes about an hour.

The Highway goes 37 miles through the White Mountains, starting in Lincoln, NH, and ending in Conway , NH (where you’ll be staying next). 

Unfortunately, there are no gas stations or food options along the Highway, so bring snacks!

All vehicles must pay a $5 entrance fee. You can read more online at KancamagusHighway.com

Here are a couple of my favorite stops:

Hancock Overlook —Located along the Kancamagus Hairpin Turn, Hancock Overlook will seriously leave you in awe with its view of rolling hills and mountains COVERED in vibrant fall foliage.

Sabbaday Falls —One of New Hampshire’s most visited waterfalls!

Click here to grab a Kancamagus audio tour!

Insider Tip: Lincoln, NH is pretty small, so you’ll be better off driving the entire Highway and staying in the Conway, NH, area.

Flume Gorge

A MUST on your drive is to stop at what’s called Flume Gorge.

It’s famous for its red covered bridge which makes a great photo spot.

To enter Flume Gorge , you’ll have to pay $18 (if you grab your pass online).

In-person passes are $21.  Click here for more details !

Fun Fact: covered bridges are known as “kissing bridges” because of their privacy. Make your way through the Highway until you reach Conway.

Where to Stay in Conway, NH

Conway, NH is a fairly big city and you’ll probably find more things to do in the North Conway area.

So when considering accommodations, try to stay there!

Here are some places to consider:

The Stonehurst Manor ($$$) —A glorious mansion in North Conway where you’ll enjoy a romantic-style room complete with a fireplace! With your stay you can enjoy free dinner and breakfast.

Ledge & Lake Chalet ($$) —A cozy chalet nestled in the White Mountains. Enjoy a fall foliage view from your windows before taking a short walk to Echo Lake!

North Conway Grand Hotel ($$) —A great hotel with everything you could ask for! Enjoy the spa, pool, and proximity to outdoor adventures. You can even cozy up in a king room complete with a personal hot tub (if that’s your style).

Insider Tip: Want a cabin getaway? Check out this guide: Cozy Cabin Rentals in North Conway, NH

Day 3 — Franconia Notch State Park (Amazing New England Fall Road Trip Sunrise)

Day 3 in Sum (Total Drive Time: ~2 hours)

• Morning: Artist Bluff
• Afternoon : Explore Franconia Notch State Park
• Evening: Check out more of North Conway

On Day 3 of your New England fall road trip itinerary you’ll get to see the popular Franconia Notch State Park and explore one of my favorite New Hampshire towns: Conway—woohoo!

Hiking Artist Bluff Trail

First stop: Artist Bluff Trail for some leaf peeping in New England this morning!

I’ve gone here for sunrise in the past, but a mid-morning hike is a great choice too!

The drive here from Conway will be about 1 hour, but it’s worth it!

The trail is about 1.9 miles round trip with very minimal elevation gain.

Artist Bluff is where you will get the famous New England foliage view of Echo Lake — prepare for your jaw to DROP . I mean, just look at the pictures.

Insider Tip: The trail gets SO windy at the top, so don’t wear anything that can fly away. 

Franconia Notch State Park

After your hike, take some time to explore the rest of the park!

Below are some attractions to consider:

Echo Lake Beach —You already saw the lake from above. Now go explore the fall-covered shoreline! Click here to book parking reservations —parking is limited.

Hike More Trails —Lonesome Lake Trail, Mt. Pemigewasset Trail, and the Appalachian Trail are more fall hikes you can enjoy.

Cannon Mountain Aerial Tramway —Enjoy fall views from 4,000 feet in the sky! Taking the sky tram up Cannon Mountain will give you views of New Hampshire, Vermont, New York, AND Canada.

This is a pretty scenic area of New Hampshire—I enjoyed just driving around!

Insider Tip: If you don’t have time to see too much, I at least recommend exploring Echo Lake — it’s just too pretty!

North Conway, NH

After your adventures, head to North Conway . 

Since you already explored the Highway yesterday, you can go straight through!

North Conway, New Hampshire like the New England mountain town of your dreams, complete with a little railroad *choo choo* and boutique shops.

It’s a gem nestled in the White Mountains.

Surrounded by endless trees that go orange in the fall, North Conway is the perfect place to snack on pumpkin spice everything while you cozy up in oversized knit scarves and sweaters.

So, duhhhhhh, it has to be a stop on your itinerary.

You can shop, eat, or hang out at Schouler Park —a large grassy area perfect for a picnic.

Make time to check out the Conway Scenic Railroad. 

If you didn’t get coffee earlier,  The Met  is the place to be! Want something sweet to end your day?

I also recommend you check out the  White Mountain Cupcakery ! Chocolate peanut butter cupcakes— SIGN ME UP.

Insider Tip: Popular food spots for when you arrive in Conway include Chef’s Bistro , Vito Marcello’s Italian Bistro , and Muddy Moose Restaurant & Pub .

Black Cap Trail (Optional)

If you’re in the mood for another hike, Black Cap Trail is great for fall foliage!

Black Cap Trail is about 610ft in elevation gain and a 2.3 miles round trip .

At the top, you’ll have sweeping mountain views of the Presidential Range .

You’ll stay in Conway again— tomorrow will be your last night here!

Insider Tip: Black Cap is a pretty easy hike, so if you didn’t feel like doing Artist Bluff Earlier, this is a great alternative.

Day 4—Crawford Notch State Park (My Fave New England Fall Foliage Stop)

Day 4 in Sum (Total Drive Time: ~1.5 hours)

• Morning: Drive to Crawford Notch State Park
• Afternoon: Visit Mount Willard Trail
• Late Afternoon: Frankenstein Cliffs & other major attractions

Today we’re heading a little bit north and going to Crawford Notch State Park where you’ll be deep in the White Mountains—prime spot for fall colors!

Crawford Notch State Park Hiking

Crawford Notch makes up a large pass that carves straight through the White Mountains.

In New Hampshire’s smallest town, Hart’s Location , Crawford Notch State Park, is the hidden mountain gem you didn’t know you needed in your life.

If everything aligns, you could see peak fall colors here, which is a once-in-a-lifetime experience.

Fall will paint the trees with the most intense red color, leaving any fall lover speechless!

One of the best parts about Crawford is that you can bring your furry friends there!

On my last trip to NE, I brought my pup along, and he LOVED this portion of the White Mountain National Forest.

And if you’re heading to Crawford Notch, you must do at least one hike !

That’s the best way to see the colors.

Here are a couple of trails to consider:

Mount Willard Trail —Hike for a jaw-dropping valley full of fall colors. The trail is approximately 3.2 miles round trip with 950ft of elevation gain. 

Frankenstein Cliffs —A more challenging trail that will take you to Arethusa Falls. Some parts of the trail will take you close to parts of the park’s railroad (Frankenstein Trestle)! 

Insider Tip: Since the park lines a small section of the White Mountain Highway, it’s pretty easy to get around.

Crawford Notch Scenic Stops

If hiking isn’t your thing, though, there are plenty of other neat fall experiences you can enjoy here:

Enjoy a Scenic Overlook —You can enjoy tons of overlooks and pullouts as you drive around Crawford. Some have views of fall foliage along the Saco Rover (the river that lines the whole park).

Ride the Conway Scenic Railroad —From Crawford Station, you can ride the Conway Scenic Railroad’s Mountaineer route, which is a ridiculously scenic fall ride through the mountains.

Go Back in Time at Willey House —Visit the historical Willey House and look at old park photographs, eat ice cream, or enjoy the surrounding outdoor scenery.

Saco River —Enjoy exploring the Saco River and the gorgeous foliage around it!

Insider Tip: For the night, you’ll stay in   Conway   again before we continue on your New England fall road trip itinerary—Maine is up next and it’ll be a longer drive!

Day 5—Acadia National Park, Maine

Day 5 in Sum (Total Drive Time: ~4 hours)

• Morning: Drive to Acadia National Park
• Afternoon: Bar Harbor
• Evening: Bass Harbor Head Lighthouse for sunset
• Stay: The Primrose , The Inn on Mount Desert , Bar Harbor Grand Hotel

Today’s leg of the road trip will take you all the way up to Maine!

Bar Harbor, Maine

Maine has to be one of my favorite states for New England fall foliage because you get a unique mix of autumn colors and ocean views.

While this is a 4-hour drive, you don’t have to be anywhere until sunset hits. 

So if you have some time to spare, grab some food in Conway and some snacks for the road before continuing your leaf-peeping New England adventures!

And the drive up to Acadia will be beautiful!

You’ll be in the mountains LITTERED with fall colors—ooo la laaa!

Bar Harbor is a town on Mount Desert Island, surrounded by gorgeous cliffs and the ocean.

Known for its stunning coastal vibes and boating, Bar Harbor is the perfect place to enjoy a lobster roll after a full day of exploring the park.

If that sounds like your vibe, you must check out  The Travelin Lobster !

You’ll spend two nights in Bar Harbor—the gateway to Acadia National Park.

Insider Tip: While you’re here, I recommend you take a tour around Bar Harbor and Acadia NP !

Bass Harbor Head Lighthouse

For your first sunset in Acadia National Park, I suggest visiting the classic Bass Harbor Head Lighthouse . 

Bass Harbor Head was constructed in 1858 and was considered significant for its aid, making transportation possible in Maine.

You may not see much New England fall foliage here, but it’s the easiest way to enjoy your first evening in Acadia National Park.

Expect parking to be limited and hectic! 

For dinner, I recommend checking out  Cafe This Way !

They have something for everyone, from fresh lobster to a vegan burger!

Cafe This Way also has a great breakfast menu, just saying.

Insider Tip: Bass Harbor Head is a popular photography spot but a must-see for visiting the park—plan to get here almost an hour before sunset.

Where to Stay in Bar Harbor

The hotels in Bar Harbor are just as dreamy as the views—check them out:

The Primrose ($$) —An elegant hotel where you’ll be just a mile from Acadia! The Victorian-style rooms will leave you in awe, but so will the fluffy pumpkin pancakes!

The Inn on Mount Desert ($$) —A charming guest home is an adorable Bar Harbor neighborhood. You’ll love staying here for its proximity to downtown and cozy beds that practically hug you to sleep.

Bar Harbor Grand Hotel ($$) —A gorgeous hotel property modeled after the elegant 19th century Bar Harbor homes that used to line the city. It’s centrally located to the beach, park, and downtown—everything is within walking distance!

You’ll start tomorrow with a sunrise mission, so get plenty of rest!

Day 6—Acadia National Park

Day 6 in Sum (Total Drive Time: ~1 hour)

• Morning: Adventure through Acadia National Park
• Afternoon: Cadillac Mountain, Jesup Path
• Evening: Beehive Trail for sunset

Today will be your time to see as many things to do in Acadia National Park as possible!

Cadillac Mountain

While exploring Acadia National Park in the fall, you may as well see the first sunrise in the USA!

During October, the sun rises over Cadillac Mountain before anywhere else in the country, so it’s a popular park attraction! 

Staying in Bar Harbor will put you about 15 minutes away. 

After sunrise, I suggest driving 15 minutes back into Bar Harbor for some breakfast! Try  Jordan’s Restaurant !

Insider Tip: To ensure you get parking, head there about an hour before sunrise. 

Hiking Jesup Path and Hemlock Path Loop

In the afternoon, head to  Jesup Path and Hemlock Path Loop !

It’s an AMAZING trail for seeing New England fall foliage.

The trail is only 1.5 miles round trip and pretty much flat the entire time. 

The loop takes about 30-60 minutes to complete, and you’ll walk along tall trees covered in color the entire time.

If you’re not up for going on Jesup, try one of these awesome things to do:

3-Hour Private Tour —Take a private tour that’ll bring you through the best of what the park has to offer including Park Loop Road, Cadillac Mountain, and Sand Beach!

Foodie Tour —Spend the afternoon exploring Bar Harbor and eat your heart out! This highly rated foodie tour will have you eating lobster rolls, crab cakes and more.

Bike Around —See all of Acadia’s best views by biking around! Rent an e-bike and you’ll get to explore the entire park on your own time all while enjoying a breezy ride through fall colors.

You can also just explore more of Bar Harbor!

Insider Tip: You don’t have to hike the entire Jesup Path if you don’t want to— turn around at any point!

Beehive Trail for Sunset

And now it’s time for sunset—hit that  Beehive Trail ! Make sure you wear sturdy hiking boots !

Beehive Trail is relatively short, sitting at about 1.5 miles round trip , and will take you up a cliffside where you’ll see coastal views and an ocean of fall colors .

You can make a loop out of the hike or turn around at the top of the main cliff.

When I hiked Beehive Trail, rather than making a loop out of it, I went to the top of the cliff and then back down the same way.

It was easier to navigate back to the car since the trail was pretty dark after the sun went down.

So pro tip, bring a headlamp for your sunset excursion! 

Insider Tip: I should also note that this hike includes ladders , which adds to the adventure, hehehehe, but if that scares you, then skip this trail.

Jordan Pond (Alternative)

An alternative would be to head to Jordan Pond and hike a 3.3-mile moderate loop around it.

You can get there by parking at the Jordan Pond parking lot on Park Loop Road.

Parking can get busy, so you’ll still have to get there early.

At Jordan Pond, you’ll get views of The Bubbles , two identical mountain formations that (you guessed it) look like bubbles—they’ll be covered in fall foliage!

Insider Tip: Tomorrow you won’t have to be anywhere until sunset for your leaf peeping New England adventure, BUT this will be a long driving day since you’ll be heading back to New Hampshire.

Day 7—Dixville Notch State Park (Best New England Fall Foliage Sunset Hike)

Day 7 in Sum (Total Drive Time: ~4 hours)

• Morning: Relax and eat in Bar Harbor, Maine
• Afternoon: Drive to Dixville Notch State Park
• Evening: Visit Dixville Notch, hike Table Rock
• Stay: Northwoods House , Home with a View , Private Cabin

Dixville Notch is pretty out of the way, but trust me when I say the trail you’ll be exploring is a once-in-a-lifetime hike.

Colebrook, NH

Tonight, you’ll be staying in Colebrook, NH.

There isn’t a whole lot going on in this part of New Hampshire, but Colebrook will have everything you need to fuel up for the next leg of the trip.

Since you don’t have to be anywhere until sunset, you could take your time getting here .

However, you also could drive to Colebrook early (about 15min from Dixville Notch), check into your stay, get something to eat, then make your way towards your sunset hike: Table Rock.

Colebrook is a small town. Some shops and restaurants close early, so this may be a good time to stop at a grocery store for snacks or food you can eat in your hotel room!

Hiking Table Rock New Hampshire

It’s one of the best hikes for New Hampshire fall foliage, and it’s easy to see why—look at the pics! 

The view sits above Lake Gloriette and is a short 1.5-mile trail . 

The only downside to this hike is that it is relatively steep in a very short distance (about 750ft in elevation gain). If you’re weak on the knees, bring trekking poles .

The parking lot for Table Rock is SMALL—plan to be there about 1 to 1.5 hours before sunset. 

Getting to the trailhead early will give you more time to relax at the top! 

When you finish your hike, I suggest going to Colebrook and grabbing some dinner;  House of Pizza  is a popular food option.

Not in the mood for a hike? You can also make a pit stop at Lake Gloriette to have a shoreline view of the colors.

Insider Tip: I imagine Table Rock would look equally great for sunrise, so if that works out better for your New England fall road trip itinerary, you could go that route. 

Where to Stay in Colebrook

For accommodations, Vrbo could be your best bet. Check out these rentals:

Northwoods House ($$) —Stay in this cozy, updated home nestled in the woods! After you explore for the day, you can come back to this home away from home and watch Netflix while you snuggle up on your extra comfy king bed. Pet-friendly.

Home with a View ($$$) —Breakfast and panoramic views of fall colors? Sign me up! Enjoy incredible views of NH from above while you make breakfast, sit on the patio, or look out your window—pictures don’t do it justice.

Private Cabin ($$) —Escape to the woods in this private cabin. A great property to stay for the night while you fall asleep to the sounds of the running stream.

Insider Tip: Tomorrow you’ll be heading into Stowe, Vermont, which will be about a 2 hour drive, so you won’t have to be up super early to continue your leaf peeping New England adventure!

Day 8—Stowe, VT and Smugglers Notch

Day 8 in Sum (Total Drive Time: ~3 hours)

• Morning: Drive to Stowe
• Afternoon: Explore Stowe, VT attractions
• Evening: Smugglers Notch
• Stay: The Stowehof Hotel , Timberholm Inn , Green Mountain Inn

I know I’ve talked about pumpkin spice, Gilmore Girls, and fall vibes a lot, but this place feels like it is meant to celebrate fall and ONLY FALL. You’ll see.

Things to do in Stowe, Vermont for Fall

There are plenty of things to do in Stowe, VT in the fall ! So let’s talk about ’em:

Eat —If you’re a veggie lover like me, then give Green Goddess Cafe a try! Not feelin’ in? Head to Piecasso pizza ! They even have vegan cheese you can sub with.

Get Lost in a Maze —The Percy Farm Corn Maze is the place to be if you want some spooooooooky fall vibes—ooooooo, enter if you daaaaAAAre.

Grab a Coffee — Black Cap Coffee and Beer is hipster AF, and we love it, but PK Coffee is where you’ll find a bomb @$$ apple crumble that tastes like an explosion of fall in your mouth—I will NEVER FORGET IT.

Sip on Some Cider —Did I mention you can drive to an APPLE CIDER MILL WHERE YOU CAN HAVE APPLE CIDER? Scott and I love Cold Hollow Cider Mill and would recommend it to anyone as a stop on their New England fall road trip itinerary.

Hop on a Zipline —get up close and personal with the fall foliage by hopping on one of the longest ziplines in the country!

Take a Brewery Tour —Enjoy some hard cider and locally brewed beers on a 5 hour, small group tour!

Click here to book your Stowe day tour!

Insider Tip: Want to see it all? Book an epic day tour that will take you to Smuggler’s Notch, the Cider Mill, Ben & Jerry’s, downtown Stowe, and the Outdoor Center at the Trapp Family Lodge for some epic views of the Green Mountains!

Smugglers’ Notch State Park

Most folks come here to explore Smuggler’s Notch Pass.

Smuggler’s Notch Pass goes through Vermont and has some fantastic New England views!

It’s well-known for its extremely windy road that bobs and weaves through endless fall colors in Vermont’s Green Mountains —don’t skip the drive!

You can spend a chill day in nature enjoying one of the Smuggler’s picnic areas.

To learn more about the park, visit  VTStateParks.com .

Insider Tip: If you want to hike around, check out Hellbrook Trail, Sterling Pond Trail, or Long Trail.

Where to Stay in Stowe, VT

Stowe is the place to book a BOUJIE hotel. This is a bucket list type town, and there are some beautiful resorts!

Check them out:

Timberholm Inn ($$) —The Timberholm Inn is tucked away in the Stowe mountains. This is the perfect place to get your cabin fix in a cozy environment that’ll put you in the middle of prime fall foliage! 

The Stowehof Hotel ($$) —Staying at The Stowehof will make you feel like you’re in a European country. The views here are spectacular, but the interior is extra special. The beautiful fireplaces and library you can enjoy will be the perfect places to rest up after a long day of exploring! Fab location too.

Green Mountain Inn ($$) —Located in Stowe’s Historic Center is this magical inn with an ornate lobby, romantic rooms, and a heated pool you’ll love! Being in the center of town will put you in the middle of all the action.

Insider Tip: If you want a shorter trip, check out my guide on a fall weekend in Vermont !

Day 9—Lake Placid and the Adirondacks

Day 9 in Sum (Total Drive Time: ~3 hours)

• Morning: Drive to Adirondacks
• Afternoon: Explore Heart Lake or Indian Head
• Evening: See Lake Placid
• Stay: Crowne Plaza Lake Placid , Mirror Lake Inn , High Peaks Resort

The drive from Stowe, VT to the Lake Placid, NY area will be about 2 hours! This is outside of New England but it’s worth the drive.

Adirondacks

When you arrive, head into the High Peaks Wilderness and hike  Indian Pass and Heart Lake Loop Trail .

Heart Lake Loop is a little over a mile and is a GORGEOUS fall foliage hike! 

You can read about parking for the trailhead on the  Lake Placid website .

Another hike I highly recommend you do is  Indian Head and Rainbow Falls . It’s an easy 11mi hike that will lead to a stunning fjord-type formation surrounded by fall colors! 

After your hike, grab a caffeine fix at  Old Mountain Coffee Company  in Keene, NY. 

They sell chocolate bars there, and I have never had better chocolate—grab one!

Insider Tip: Alternatively, you can go to Mirror Lake and walk the shoreline—another popular destination in the area.

Lake Placid

Lake Placid, New York, is known for its access to the outdoors and, more notably, the winter Olympics—and it’s where you’ll stay for the night!

Mirror Lake sits in the town center.

When you get here, I recommend taking a walk in the downtown area.

It is quaint, cute, and ADORABLE in the fall and has lake views everywhere.

You can shop along Main Street, grab a pastry, or  rent a canoe  and coast along Mirror Lake.

OR, if you want an authentic New England fall foliage adventure, you can get a view of the foliage from above by booking a scenic flight with Payne’s Air Service.

Insider Tip: For food, I suggest capping off your last official day in your fall road trip in New England with a drink and some food at  Lisa G’s !

Woodstock, Vermont (Alternative)

If seeing the Adirondacks doesn’t feel like your vibe, I recommend staying in Stowe, VT, another night and taking a day trip to Woodstock, Vermont .

The drive will be about an hour.

You can enjoy more of Vermont’s fall foliage when you’re there and explore the quaint Woodstock area.

We’ll talk more about Woodstock, VT in our “BONUS” stops section—keep reading!

Insider Tip: Woodstock is also home to the Sleepy Hollow Farm—a must-see for spooky fall vibes!

Where to Stay in Lake Placid, NY

Like Stowe, Lake Placid has some amazing places to stay.

Here are my recommendations based on previous trips I took here:

Crowne Plaza Lake Placid ($$) —This amazing hotel includes all the amenities you need for an extra comfortable stay and has a GORGEOUS view overlooking Mirror Lake.

Mirror Lake Inn ($$$) —A fantastic property overlooking Mirror Lake that has the perfect spa to end your trip with. The entire time you’re there, you’ll enjoy panoramic views of the Adirondacks!

High Peaks Resort ($$) —Located right in the middle of all the action, this gorgeous resort has private beach access you can use to enjoy Mirror Lake and the surrounding foliage. Pet-friendly too!

Insider Tip: Tomorrow will be a travel day back to Albany, New York!

Day 10—Drive to Albany, NY

Day 10 in Sum (Total Drive Time: ~2 hours)

• Morning: Drive to Albany, NY
• Stay: Albany, NY, or depart

Now it’s time to wrap up our New England fall road trip!

Drive to Albany

This day is short and sweet.

You’ll be driving the 2-hour drive back to Albany, New York, where you might be departing, or you will stay the night and leave the next day. 

Either way, plan your travel accordingly!

If you have time to grab coffee before leaving Lake Placid, I suggest trying  The Coffee Bar !

The lake views here are *chef’s kiss* and will be a great way to cap off your leaf-peeping New England adventure.

Otherwise, that’s a wrap!

Let’s quickly discuss what this trip would look like if you started in Boston, MA.

Insider Tip: Additionally, you can head to the New York Catskills to see more fall foliage (covered in the bonus sections).

BONUS New England Fall Road Trip Itineraries

Let’s quickly go over the other ways you call pull this trip off.

After this, we’ll talk about bonus stops!

10-Day Fall Road Trip in New England Starting in Boston

Alternatively, you can arrive at the Boston-Logan International Airport and drive 2 hours to Conway, NH. 

This would mean your first night would be in Conway, NH. 

You would then proceed with days: 2 through 8 from the Albany itinerary.

Then, on day 9, head towards Boston and stop in Woodstock, VT.

Woodstock, VT is where you can see the Sleepy Hollow Farm. 

Finally, on day 10, you can explore Boston, MA, and prepare to depart!

The map below illustrates what your route would look like.

5 Day New England Fall Road Trip Itinerary

Only have five days?

I recommend flying into Manchester, NH, and focusing your time and efforts on seeing New Hampshire and Vermont.

In that case, fly into Manchester, NH, and drive about 2 hours to Conway, NH.

With Conway as your hub, you can have a BLAST exploring the White Mountains (days 2 through 4) AND make a stop in Stowe, VT (day 8).

If you end in Stowe, you’ll have a 2.5-hour drive back to the Manchester area. 

3 Day Fall Foliage Trip

If you only have three days to work with, I suggest exploring New Hampshire fall foliage.

You can spend three days going around the White Mountains and have a fantastic time!

A road trip like this would look similar to days 2 through 4 on our extensive itinerary.

You’d fly into Manchester, NH, and stay in Conway, NH.

If you’re up for it, take a day trip to Stowe from Conway (about a 2.5-hour drive).

New England Fall Foliage Bonus Stops

Regardless of where you start your trip, you should know that there are plenty of unique places we didn’t cover!

Want to switch things up or add additional destinations to your fall road trips in New England?

This section is for you.

Sleepy Hollow Farm in Woodstock, VT

Spend an extra night in Stowe and take a day trip to Woodstock’s Sleepy Hollow Farm. It’s possibly one of the most photogenic farms in Vermont. The best part?

The farm is less than an hour from Stowe, so you don’t have to drive too far! 

If you can, I recommend exploring Woodstock during the day.

You’ll enjoy some hella New England vibes and great coffee (like at Soulfully Good Cafe ). 

Connecticut

If you’re looking to  switch it up , add Connecticut to your list!

During your East Coast fall road trip, you can opt to take Route 9 through the Connecticut River Valley. 

And if you want a unique way to see fall colors, ride on the historic  Essex Steam Train ! 

The Essex will take you on a scenic journey through some of Connecticut’s most beautiful fall views. 

For an authentic leaf-peeping New England experience,  try a fall foliage cruise  (available in other New England states too).

Portland, Maine

There is so much to do in Portland, Maine !

You can go apple picking or even take a tour of a Sugar House where a farmer will let you try some of their fresh maple syrup. 

For example, Merrifield Farm and Sugar Shack have maple cotton candy and fresh vanilla ice cream with maple syrup visitors can buy.

Of course, you can get pancakes here too!

AND…AND, if you want to have a real Portland, Maine experience, you can  book a fall foliage private sightseeing cruise . 

Honestly, I don’t think it gets any more New England than that.

Make sure you grab a lobster roll and head to Portland Head Light too!

Catskills, New York

This region ended up being one of my favorite spots during my fall road trips in New England!

The Catskill Mountains Scenic Byway is a great place to end your fall foliage adventure. 

Minnewaska State Park will make all your leaf-peeping dreams come true! For some of the better foliage views,  hike to Kaaterskill Falls . 

If you’re into cabin vibes, I suggest booking a stay in a luxe country home like this for the night.

It is spacious and has a hot tub, one of my favorite ways to end a long trip. 

The Lake Minnewaska area is about 2 hours from Albany airport.

Finger Lakes Area

In New York, I suggest visiting Taughannock Falls State Park or Watkins Glen at some point on your New England fall road trip itinerary. 

Both of these stops are in the Finger Lakes National Forest area.

It’s a bit out of the way, but it could be worth the visit if you want to explore more of New York.

You can also opt to visit the Seneca Lake area and do a whole  Seneca Lake Wine Tasting Tour . 

I have PACKED this New England fall road trip itinerary with some of my best fall color recommendations.

Whether you’re a fellow PSL lover or just a fan of autumn, I genuinely hope you enjoy your East Coast fall road trip! If you want to see more epic fall adventures, I recommend checking out my New England blogs!

If you enjoyed this blog, please share it on Pinterest !

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When is a great time to go in the fall?

Very helpful. Thanks a lot for posting this!

Amazing recommendations! Thank you so much for doing this!

Amazing post…Thanks for sharing…

Hi Dani, Help ,,, need your clarification please, is table rock – Dixville notch state park, is it located in New Hampshire or Vermont ? By any chance if you could remember what state highway or Interstate freeway you took, your help will be greatly appreciated and thank you in advance Sally

Your itinerary is a great help, we’ll follow your suggestion. Thanks for sharing and greatly appreciated !

Hi Dani, this is the best new england trip suggestion I’ve read. Thank you so much for sharing and appreciate every detail you put in!

I have used your New England itinerary for our upcoming fall color tour. However I am having a hard time printing it out. We are arriving inAlbany, New York via Amtrak and continuing on for your 10 day trip starting at the Berkshires and ending in Lake Placid. If you can would you be so kind as to email it to me so I can print it off. I want to follow most of your recommended places to visit and would like a printed copy( seniors, lol) to take along with us. We are leaving on 10-1 21 from Chicago. Any additional tips would be appreciated. Thanks so much.

Sandra Loerop

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I watched about 10 traveling videos this week trying decide where to go. And this post the best one by far best. Shows pics and personal videos, didn’t spend to much time on each place

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I'm a burrito loving explorer who got fired from corporate America and turned that into my dream career as a photographer and blogger. Now I'm here to help you explore life's magic. Thanks for stopping by!

Planning a New York to Maine Road Trip Itinerary

Whether you are going for the beaches and the lobster rolls, or trying to hit peak fall foliage and everything pumpkin and apples, May through October is the perfect time to plan a New York to Maine road trip.

While it is tempting to rush through Southern New England on your way from New York to Maine, take some time to stop and see the sights along the way. This New York to Maine road trip itinerary was designed for a one-week trip, but can easily be extended to include more time at each destination or you can continue up the Maine Coast to see more of Vacationland.

This road trip is designed to go from New York City to Portland, Maine. However, if you want to include more stops between New York and Boston, you will also want to look at my New York to Boston itinerary for additional ideas.

Or, if you want to see more of Maine, you can continue north for a road trip through the Maine Highlands . This itinerary will take you from New York City to Maine, with stops in:

• Mystic, Connecticut
• Newport, Rhode Island
• Boston, Massachusetts
• Portland, Maine

New York to Maine Road Trip

If you are taking a New York to Maine road trip, the quickest route will be under six hours through Hartford, Connecticut. This makes the best return trip from Maine, but on your way, I’d recommend taking a slightly longer and a smidge more of a scenic route on your way to Maine.

From New York City, take Interstate 95 approximately 3.5 hours (traffic can vary) to the historic seaport town of Mystic, Connecticut. If you need a pitstop along the way, downtown Stamford and New Haven both offer great dining options, or grab some lobster rolls at Ford’s Lobster in Noank, Connecticut.

Stop #1: Mystic, Connecticut

Your first overnight stop should be in the charming seaside town of Mystic. I’m not sure if it is more famous for Mystic Pizza, the 1988 film starring Julia Roberts, or the historic Mystic Seaport, a must-see family attraction. You will probably want to stay here for two nights, as there is plenty to do in town and nearby.

Mystic Seaport is a recreated 19th Century seafaring village, complete with ships, shops, and workplaces staffed with costumed interpreters ready to tell you about their craft and day-to-day life in a 19th Century town. The cooperage, print shop, and general store are all popular stops with kids. Visitors can also step on board the Charles W. Morgan, the last wooden whaling ship in the world, or get out on the water on a Mystic River boat ride.

Downtown you can grab an ice cream and watch the drawbridge go up and down as ships pass by, browse the shops, or get something to eat at one of the many seafood restaurants. In addition to Mystic Pizza, I’m a huge fan of the Engine Room for lunch or dinner, or Kitchen Little for breakfast.

Kids will also love watching the beluga whales at the Mystic Aquarium or exploring the trails at the Denison Pequotsepos Nature Center. If you are visiting in the fall, it is worth waiting in line at B.F. Clyde’s Cider Mill for some hot, fresh apple cider donuts.

If you have time to spend a couple of days, nearby you can enjoy a ride on the Essex Steam Train, a visit to the Pequot Museum on the land of the Mashantucket Pequot Nation, a lighthouse tour from New London, a day at the beach in Misquamicut State Beach in Westerly, Rhode Island, or some wine tasting at Jonathan Edwards Winery near Stonington, CT.

Read more: things to do in Mystic with kids

Where to stay: Hyatt Place Mystic (includes free breakfast) and Mystic Marriott Hotel & Spa (not in downtown Mystic but a good full-service hotel option).

Stop #2: Newport, Rhode Island

From Mystic, it is about one hour drive to your next stop in Newport, Rhode Island. You can potentially just visit for the day and continue on to Providence or Boston, but staying overnight will give you more time on the Classic Coast.

Whether you are visiting in the spring, summer, fall, or winter , there is always something to do in the historic town of Newport, Rhode Island . Once a summer getaway for the wealthy New York industrialists, Newport still attracts the yachting crowd as the “sailing capital” and the classic coast. You can do Newport in a day, as it is only an hour from Mystic, but if you want to enjoy nearby beaches, farms, or take a day trip to Providence, Rhode Island , plan on staying one to two nights.

Two must-do things when you are in Newport are paying a visit to at least one of the famous Newport Mansions and getting out on the water for a sailing tour. The Newport Mansions are former homes of the business titans like the Vanderbilts, which were once used as “summer cottages” but more closely resemble palaces than a beach house. The largest and most famous is The Breakers, but I also enjoy visiting Marble House.

If you don’t want to tour the homes, take a drive down Bellevue Avenue to see them from the front and then walk along the three-mile Cliff Walk to get a glimpse of some of the backyards, along with gorgeous ocean views.

There are many sailing options in Newport, from sunset schooner sails to seal-watching eco-tours (in the winter). Leave time to enjoy shopping and strolling along Thames Street and Broadway in downtown Newport. You can also pop into the International Tennis Hall of Fame or one of two car museums around town. There are plenty of options for a great meal, including Bowen’s Wharf, the Black Pearl, Diego’s, and Midtown Oyster Bar.

In the evening, be sure to take a drive along Ocean Drive and try to catch a sunset from either Brenton Point, the Lawn at Castle Hill Inn, or Newport Island Harbor Resort on Goat Island. On your second day, either hit the beach (my favorites in Newport are Gooseberry Beach and Second Beach) or take a drive over to the neighboring island of Jamestown to visit my favorite spot in Rhode Island, Beavertail State Park. If you prefer an urban outing (or if you are visiting on a Waterfire night), head up to Providence for the day or afternoon/evening.

Where to stay: Newport Marriott has a great location and nautical decor, The Brenton Hotel is a hip hotel in central waterfront location, and The Vanderbilt is an upscale, historic property with a great rooftop bar.

Stop #3: Boston, Massachusetts

When it is time to bid adieu to Rhode Island, drive two hours north to Boston. Now if you have extra time, you will want to spend three days in Boston, especially if you want to take some day trips to Gloucester , Rockport, or Salem, or stop at Plymouth along the way.

Boston is rich in history and charm, and like any large city, it has its fair share of great museums too. If you are interested in history, taking a walk along the Freedom Trail is a must-do. Of course, you may get more out of it if you sign up for a tour with a costumed guide.

To better understand Boston’s pivotal role in the Revolutionary War and founding of the country, pay a visit to the Boston Tea Party Ships & Museum . Kids will especially love tossing the tea into the Boston Harbor or a snack at the tea shop.

Within a short walk of the Boston Tea Party Museum, you can also visit either the Boston Children’s Museum or the New England Aquarium. If you are visiting in the summer, I’d recommend booking a whale-watching cruise in advance for an afternoon on the water and a glimpse of some magnificent creatures. If you don’t have time for a whale watch, you can still enjoy some time on the water with a harbor cruise or a ferry around the Boston Harbor Islands.

Afterward, take a walk along the Rose Kennedy Greenway and either enjoy some of the food trucks congregated there, or walk over to the North End, Boston’s “Little Italy” and pick up some cannoli at Mike’s Pastry. And while it is touristy, the street performers around Fanueil Hall are always entertaining and there are plenty of places to grab a quick bite. For a more upscale food hall, drop into the Boston Public Market or head across town to Eataly Boston.

Sports fans should try to book a tour of the “Green Monster” and Fenway Park or try to catch a Boston Red Sox game in this classic stadium. If you appreciate art, visit the Museum of Fine Arts, or the intriguing Isabella Stewart Gardner Museum nearby (and learn about the famous heist that took place there.)

While you are in town, take a stroll through the Boston Common and Public Gardens, and take a ride on a Swan Boat before you visit the famous “Make Way for Ducklings” sculpture. You can also pop into Cheers on Beacon Hill and see if anyone knows your name. Movie and television fans would also enjoy a tour with On Location Tours of popular Boston filming sites from Good Will Hunting, Ted, The Departed, and others.

Read more: Things to do in Boston with teens

Where to stay : Boston is notoriously pricey, so for a family, you may want to consider one of the following options: Residence Inn Boston Downtown/Seaport Hotel has a convenient location to downtown, North End and harbor; Element Seaport is in newer seaport district with family size rooms; and Hyatt Place Boston/Seaport District has free breakfast and a good location in popular Seaport District.

Stop #4: Kennebunkport, Maine

On your way to Portland, head two hours north of Boston to the charming coastal town of Kennebunkport, Maine. As soon as you pass into Maine, get off the highway and hightail it to Bob’s Clam Hut for some of the best lobster rolls and fried clams in New England. Then meander up the coast, taking your time to stop into a few of the best towns in the Maine Beaches region.

If you need to stretch your legs, stop in York for a walk along the 1.5 mile Cliff Walk or stock up your kitchen pantry at the Stonewall Kitchen company store. Another must-stop destination on your road trip to Maine has to be in Cape Neddick at the Nubble Lighthouse. Located on an island just off the coast, this is one of the most photographed lighthouses in Maine. If you are hungry, you can get some fresh lobster at Fox’s Lobster House right next door or Dunne’s Ice Cream down the street.

Just a little further along you will arrive in Kennebunkport (you might want to drive past the Bush Family compound along the way.) In town, you can enjoy shopping and dining at the many restaurants such as Federal Jack’s, Allison’s, Mabel’s, or the famous Clam Shack.

We also like to head out of town to Cape Porpoise Chowder House, which is popular with locals and tourists alike. Just be warned that parking is hard to find so you may need to walk a bit. You can stay in Kennebunkport or drive another 40 minutes to Portland, Maine. Your final destination on this New York to Maine road trip.

Where to stay: The Boathouse is a waterfront hotel right in Dock Square is perfect for when you want to be in the center of the action. If you prefer a bed and breakfast, try the The Inn at English Meadows .

Stop #5: Portland, Maine

Portland , Maine is one of the best small cities on the East Coast . Plan to spend at least a couple of days exploring Portland and the surrounding area. The park and area around Portland Head Light in Cape Elizabeth is a perfect spot for a picnic and to clamber over the rocks and watch the boats go by. When you are there, be sure to pick up a lobster roll from the Bite into Maine food truck.

Back in Old Port, take an afternoon to explore the boutiques along the harbor and wharves. There are so many amazing restaurants in Portland to try including Luke’s Lobster, Duckfat, Eventide, and Fore Street. There are also many craft breweries in the Portland area and you can board the Brew Bus for a tour if you don’t want to risk driving.

On your second day, you can take a ferry around the Harbor Islands or try a lobster cruise where you learn all about lobster fishing and even get to keep and cook what you catch. Or, spend a day shopping up in Freeport, home of the flagship L.L. Bean store.

Read more: Things to do in Portland in winter

Where to stay: Press Hotel or the AC Hotel Portland

While this New York to Maine road trip itinerary only takes you into Southern Maine, it is easy to extend this to head up to the coast with a stop at either Boothbay Harbor or Rockland before reaching Bar Harbor and Acadia National Park .

This road trip gives you a great introduction to Southern New England and includes some of the region’s highlights. If you are looking for more road trip ideas and want to dig a little deeper into New England, I’d recommend:

• New England road trips to take in the fall
• Vermont road trip itinerary
• Off-the-beaten path Maine road trip

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Tamara Gruber is the Founder and Publisher of We3Travel. A former marketing executive and travel advisor, Tamara is an award-winning travel writer and recognized expert in family travel. Tamara is a member of SATW and the Adventure Travel Trade Association, and serves on the Board of the Family Travel Association. She is also the publisher of YourTimetoFly.com and the co-host of the Vacation Mavens travel podcast.

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Publish Date: March 23, 2024

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