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10 Most Charming & Best Towns in the Berkshires (+ Places to Visit)

Looking for the best towns in the Berkshires to visit? You’re in luck! We are breaking down the best places to visit in the Berkshires, the gorgeous region in Western Massachusetts bordering the state of New York. 

Famous for its performing arts scene, Gilded Age mansions, sprawling landscape, and outdoor recreation, not to mention the beauty that’s inspired creatives for generations, as well as a place for peace and retreat from the chaos of New York City dwellers.

There are many incredible things to do in the Berkshires that make this an ideal getaway, including the incredible towns in the Berkshires dotted along Route 7. For the purposes of this guide, we will focus primarily on the best-known towns in the Berkshires along Route 7.

We will also recommend some of the best attractions and things to do in each of these towns that make these destinations some of the best places to visit in the Berkshires!

To get your bearings, the town of Pittsfield, Massachusetts is a good central point for the region. Anything north of Pittsfield is considered ‘North County’ and anything south is considered ‘South County’. 

There are plenty of incredible places to stay and visit in the Berkshires, but if you’re looking for where to base yourself for exploring the entire region, this is a great central point and we will give our hotel recommendation at the end of this guide.

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Towns in the Berkshires to Visit

On the southern end of Route 7, you’ll find Sheffield. It’s the oldest town in Berkshires, incorporated in 1733. It’s set on the lush banks of the Housatonic River and its many offshoots. The town includes the Village of Ashley Falls to the south before you reach the Connecticut/Massachusetts border.

Route 7 runs through the middle of the entire town, and if you drive along the length of it, you’ll find a variety of different things to do. It’s one of the best places to visit in the Berkshires if you are interested in antique shops, which you can find all along the highway!

Art fans will want to check out the seasonal Butler Sculpture Park and its modern metal sculptures. The artist, Robert Butler, owns the land and if he’s around he’ll happily show you around the property.

Or if you’re interested in the unexplainable, there’s the fascinating  Thom Reed UFO Monument Park off Cook Road. It’s the only UFO incident site that’s been recognized by multiple departments of the US government!

There are also a few historic sites, like Shay’s Rebellion Memorial Monument on Sheffield-Egremont Road. The site is also along the portion of the Appalachian Trail that runs through South County.

And further south in Ashley Falls is  Ashley House , the oldest home in South County. It was built in 1735 for Colonel John Ashley House, who was largely responsible for settling the region. Today it’s a museum you can visit.

Adjacent to the house is  Bartholomew’s Cobble , a nature preserve. If you are a fan of local fauna and flora, this is the place to come to in South County. It’s a unique bio-reserve full of plants and animals that you don’t normally find in the same region! You’ll find nature trails and moderate hiking trails that are especially great if you come in the fall.

• Great Barrington

Heading north on Route 7 the next Berkshires town to check out is Great Barrington. This is definitely the happening scene for South County! The town has a few claims to fame. Its Main Street was the first in the US to have electric lights! And the Civil Rights activist W.E.B. Du Bois was born here. You can visit The Homesite  which commemorates his life and accomplishments.

The downtown area is really what makes this one of the best towns in the Berkshires. Great Barrington’s Main Street merges with Route 7 through Great Barrington for about 4 miles of great shops, restaurants, art spaces, and more.

Check the lineup at the  Mahwaie Performing Arts Center . It’s a gorgeous century-old theater that hosts concerts, theatrical performances, comedians, and even cultural events.

Or there are several art galleries like the  Bernay Fine Art Gallery . They do an impressive job of showcasing contemporary artists across many different mediums.

If you have the shopping bug, there are tons of fun shops downtown ! You’ll find vintage clothing stores like The Boho Exchange, so many women’s boutiques, and designer home goods stores like Sett. It’s also a great food scene with pubs, ice cream shops, and restaurants. 

The Prairie Whale   is famous for its elevated American food and you should definitely reserve a table for dinner! If you’re looking for something more casual, check out Barrington Brewery & Restaurant, they make some great beers!

Downtown is home to the  Housatonic River Walk , which is a nice half-mile natural trail along the water with informational and historic plaques about the area. And if you’re willing to drive a few miles out,  The Egremont Barn  is a must. It’s a great bar with a fun atmosphere and excellent drinks. 

Just north of Great Barrington is Monument Mountain where you can enjoy easy-to-follow hiking trails that are color coded for difficulty. You’ll see interesting quartzite formations and great views of the Housatonic Valley.

And for more outdoorsy attractions, there’s also East Mountain State Forest where Butternut Ski Area offers different activities every season.

• Stockbridge

If you’re looking for places to visit in the Berkshires to get away from it all, consider Stockbridge. It’s home to the Kripalu Center for Yoga and Health , which is the yoga mecca for the US. People come here on retreats, for workshops, or even to receive professional training. You can plan a whole vacation here or just a day visit.

Fans of Norman Rockwell will want to take a walk along Main Street in Stockbridge. It almost feels like you’re stepping back in time with 19th-century storefronts and American flags. If it feels like a Norman Rockwell painting, that’s because it was! Rockwell had his home and studio here until he passed away. You can visit the  Norman Rockwell Museum  and see where he worked.

Those interested in Gilded Age Mansions will not be disappointed when visiting the Berkshires. In Stockbridge, there’s  Naumkeag  and  Chesterwood , both of which you can tour and see the mansions and gardens. Or take a drive to the  Berkshire Botanical Gardens  with its themed gardens and contemporary art gallery.

A really cool place to stay in Stockbridge is the  Red Lion Inn . It’s a gorgeous New England-ambiance hotel offering elegant rooms that feels frozen in time and is one of the best places to stay in the Berkshires! The Widow Bingham’s Tavern at the hotel dates back to 1773! This is actually one of the oldest continuously operated hotels in the country that’s hosted numerous notable figures throughout its long history, including presidents, authors, and artists.

And if you want to see a classic Berkshire theatrical performance , check out the Unicorn Theater on East Street or the Fitzpatrick Main Stage on East Main.

• West Stockbridge

West Stockbridge is a small town along the Massachusetts Turnpike between Route 7 and the New York/Massachusetts border. It’s the perfect rustic Berkshire town with green pastures, rivers, ponds, and forests surrounding it.

And small as it is, the town has made a name for itself with unique art attractions, not to mention you’re just a few minutes’ drive to all the great attractions in Stockbridge too.

Downtown there are a handful of art galleries, and then there’s the  TurnPark Art Space . This is a cool sculpture park with an art museum. The presentation is stunning with sleek, modern sculptures positioned among the textures of nature.

Or if you prefer historic sites, check out  Shaker Mill Books  on Depot Street. Locals call the 170-year-old grist mill The Barn. Today it’s a beautiful setting for a unique bookstore!

Graham Farmhouse Winery in West Stockbridge is just one of the many amazing wineries in the Berkshires. They sell honey-based wine at  the local farmers market  and at their tasting room on Woodruff Road and W Center Street (by appointment only).

Or if you want to try  Charles Baldwin & Sons’  famous extracts, head downtown. You’ll find the historic storefront that dates back to 1888! Stop in and peruse all the unique extracts, syrups, souvenirs, and more. They are most famous for their vanilla extract, so this is a great souvenir or gift to pick up while you’re in town!

If you want to get outdoors, Olivia’s Overlook is a nature reserve less than 3 miles from town. There, you can explore 6 miles worth of trails that include homestead ruins. And Stevens Glen nearby is a hidden gem of West Stockbridge! There’s a moderate 45-minute trail in a stunning ecosystem full of waterfalls, hemlocks, mushrooms, spring salamanders, and more.

We think the perfect end to a day in West Stockbridge is an evening at  The Foundry . It’s a cozy, intimate performance art space with indoor and outdoor spaces. 

One of the most gorgeous places to visit in the Berkshires is Lenox. Back on Route 7, it’s just a few minutes from West Stockbridge! It’s the fanciest of the Western Massachusetts towns, with a cluster of Gilded Age Mansions and luxury resorts.

Take a tour of  The Mount , the circa-1902 mansion owned by writer Edith Wharton. Or study the beautiful brownstone architecture of the 19th-century  Ventfort Hall .

And if you’ve ever wanted to know what it feels like to live in a Gilded Age Mansion, you’re in luck! One reason why Lenox is one of the best towns to visit in the Berkshires are the number of resorts, hotels, and wellness retreats are set in their historic manors and mansions!

Blantyre  is stunning with sprawling grounds, tennis courts, and ivy-covered buildings. This was built in 1902 as a summer retreat for Robert W. Paterson and has since been meticulously restored to preserve its original grandeur, showcasing the Gilded Age charm and architectural splendor of the era.

Wheatleigh  is a stunning ivory Italian-style mansion that’s famous for Portico, its super exclusive French gastronomy restaurant. This is where you can enjoy Old World elegance (with modern amenities of course) at this refined, luxury hotel that was built in 1893 as a summer cottage for the daughter of a wealthy New York financier.

There’s also the holistic retreat at   Eastover  that offers different kinds of retreats, the estate dates back to 1910 and was the summer mansion for a prominent New York attorney at the time.

And massive, luxury  Canyon Ranch Lenox  contains the Bellefontaine Gilded Age Mansion. 

Most people associate the Berkshires with the prestigious  Tanglewood , which is located in Lenox. It’s the summer home of the Boston Symphony Orchestra but the institute hosts events all year round across multiple venues, it’s actually considered one of the top attractions in the region.

And a huge attraction in Lenox itself is the Shakespeare & Company  program. They have a popular summer season, but host actor workshops and performances the rest of the year!

Enjoy the beauty of nature around Lenox by visiting the  Pleasant Valley Wildlife Sanctuary . You can go on easy to strenuous hikes and see forests, wetlands, and fields of wildflowers. Many beavers make the sanctuary their home and you can see their dams and read educational markers to learn more about the animals!

Or book a ride on a train at the  Lenox Station Museum . You can choose between modern or vintage train cars, book a fall foliage train in the fall (which actually departs from the town of Adams, not Lenox), or visit the seasonal museum during the summer.

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Lee is a very small town in the Berkshires that’s really close to Stockbridge and Lenox along the east end of Route 7 along the Massachusetts Turnpike. Today, it’s known as “the gateway to the Berkshires,” because of the area’s rivers, streams, forests, and reserves. There are several inns, cute bed and breakfasts, and resorts in and around Lee that would make for a great launch pad for your Berkshire adventures!

You’ll find the October Mountain State Forest on the northeast side of Lee. This massive state park is the perfect place for hikers and cyclists of all skill levels. You can go camping in a tent, RV, or even a yurt! And the forest is also the starting point for many taking the Appalachian Trail, which runs north and south through the center of the park.

Back in Lee, you’ll find several cute shops, cafés, and restaurants along Main Street . Joe’s Diner is a super charming spot to grab a bite to eat. And a lot of people go to the Lee Premium Outlets while they’re here.

Or you can also visit the South Lee Historic District , a mile-long stretch of Pleasant Street along the Housatonic River. You’ll see white picket fences, 19th-century inns, taverns, churches, and a centuries-old paper mill.

While you’re in the area, make sure to drive south about 4 miles to  Santarella Gardens . Also called “The Gingerbread House,” it was built in 1920 by the English sculptor Sir Henry Hudson Kitson. It features the Arts and Crafts style that was popular at the time. The entire property and all of its buildings look like something out of a fairytale!

While Santarella Gardens is a private event venue that’s not open to the public, you can see it from the road when you drive by or stay at their other building on the property from their Airbnb listing .

Pittsfield is the center point of western Massachusetts and our this was our first introduction to small towns in the Berkshires! When you’re planning places to visit in the Berkshires, this is a great central area to stay and use as your base since it’s smack dab in the middle of the region. Plus, there are tons of great things to do in Pittsfield worth checking out!

Downtown you can visit the small but impressive Berkshire Museum . Or just take a stroll in the area between North Street and First Street. There are so many beautiful churches, old storefronts, and a great foodie scene.

You might not know that Pittsfield is also where baseball was first mentioned.  This is a relatively recent discovery . A historian came across a law dating back to 1791 referencing baseball in Pittsfield. This predates previously known baseball references by almost 50 years! Plus, the first college baseball game was historically played in Pittsfield between the locals Amherst and Williams College in 1859. 

There are also many historic sites in Pittsfield, which attracted creatives for centuries with their natural beauty. Fans of Herman Melville can visit his home,  Arrowhead , where he wrote Moby Dick and other famous works!

Or you can see how Shakers lived over 150 years ago at the  Hancock Shaker Village , a living museum with an active agricultural community just a short drive away.

Snow bunnies can hit the slopes at the small but historic Bousquet Ski Area . Or you can enjoy scenic views and miles of trails at Pittsfield State Forest .

In the summer, there’s swimming and canoeing on Onata Lake . And just north, Pontoosuc Lake is a stunning place to go boating. There’s also  The Proprietor’s Lodge  restaurant where you can dine with great views of the lake.

Another one of the best towns in the Berkshires to explore moving further up to North County is the town of Adams. This town is historically known for its industrial past, specifically its role in the manufacturing of textiles and paper.

This Berkshires town is nestled between the picturesque Mount Greylock State Reservation and Savoy Mountain State Forest and offers beautiful landscapes and views along with a charming New England countryside ambiance.

Adams boasts several attractions and historic points of interest, including the Susan B. Anthony Birthplace Museum , which showcases the life and achievements of the prominent suffragist.

Another notable landmark is the Adams Free Library , an architecturally stunning building that houses a collection of books and artifacts.

Adams is also located near Mount Greylock , the highest peak in Massachusetts, providing opportunities for outdoor activities like hiking and scenic views with a very scenic drive to the top.

And one of our favorite things we did in Adams was take the a scenic Hoosac Valley train ride . The Berkshire Scenic Railway Museum (whose museum location is in Lenox) offers seasonal scenic train rides along the Ashuwillticook Rail Trail on a historic train and is not to be missed! We enjoyed our ride in the summer, but the fall is stunning with all the foliage!

And speaking of the Ashuwillticook Rail Trail , you can enjoy a scenic walk along the old railway line that runs 12.7 miles in total! There’s a paved path next to the train tracks and this is an especially scenic walk any time of the year.

• North Adams

From Pittsfield, continue north on Route 7 and turn west on Route 2. Known as “The Town of Steeples and Peaks,” you’ll enjoy the iconic views as you arrive in North Adams, Massachusetts .

It’s truly one of the best Berkshire towns offering a beautiful downtown and it’s a great base for the North County ski resorts. North Adams is also mere miles from Williamstown, another great Berkshire town.

Along Route 2 as you enter downtown, you’ll love the rolling foothills of the Hoosac Mountain Range . There are red brick New England buildings and 19th-century storefronts downtown and the striking MASS MoCA , the enormous and impressive contemporary art museum housed in an old factory complex. We spent 3 hours here and it wasn’t enough and we wish we had more time!

A block south along Main Street are more quaint historic buildings, shops, churches, and restaurants. From here, if you turn south on Church Street, it’ll take you to the Massachusetts College of Liberal Arts which was established in 1894. 

Natural Bridge State Park   is a must-do, with its stunning white marble formations, interesting hiking trails, gorgeous waterfalls, and cool bridges!

And while you’re in North Adams, it’s the perfect time to visit the famous Mount Greylock , Massachusetts’ highest peak. There’s an incredible scenic drive with hairpin turns as you make your way to the top, this is where you’ll find the Veterans War Memorial Tower and scenic vantage points.

Plus, if you want to hike a small part of the Appalachian Trail ,  there’s a trailhead in North Adams  that takes you across the peak of Mount Greylock! But be ready for a challenging hike!

• Williamstown

Next to North Adams in North County is Williamstown. Like North Adams, it’s a great base for the North County ski resorts, like  Berkshire East Mountain Ski Resort . Or closer to Williamstown is  Jiminy Peak Mountain Resort . These are actually really close to the Southern Vermont border, which also has great ski resorts too!

There’s a huge cultural arts scene in this small town, despite looking like a sleepy Berkshire village! That’s probably because Williamstown is most famous for being home to Williams College , a liberal arts college that dates back to 1793. They make Williamstown one of the top places to visit in the Berkshires for art education, not to mention the campus is stunning.

Visit the Williams College Museum of Art  for tours and exhibits across genres and eras. And the  Clark Art Institute  is another incredible museum and gallery to visit featuring a beautifully curated collection of European and American artworks spanning from the Renaissance through the early 20th century, featuring masterpieces by artists such as Renoir, Monet, Degas, Turner, and Winslow Homer.

If books are more to your liking, stop by the  Chapin Library  on campus. It’s famous for its huge collection of rare books and original manuscripts. You can even see original copies of famous writings like the Bill of Rights and the Articles of Confederation.

And if you’re in the Berkshires during the summer, make sure to attend the  Williamstown Theatre Festiva l . This is a Tony Award-winning theatre fest with performances and events held across July and August.

Where to Stay in the Berkshires

There are so many amazing towns in the Berkshires to visit, if you’re looking for a centrally located base, we recommend staying in Pittsfield. We stayed at Hotel on North , a local boutique hotel that really honors its small town roots through its design and is a really great stay.

Local owners David and Laurie Tierney have done an outstanding job restoring and preserving the original architectural details and curating individually designed rooms featuring works by local artists in the historic building. Speaking of that art, if you LOVE the art you see on display, you can purchase it!

Choose from a range of standard and premier rooms, as well as suites. If you want a truly unique experience, see if the Library Suite is available during your stay. This room is surrounded by books and looks like a library!

All of the rooms feature impeccable interior design with early American elements combined with modern textures and shapes. Our room had a great clawfoot tub which was really nice to soak in after all of the fun things we did during our weekend in Pittsfield.

During your stay, enjoy The Gallery. It’s a small, curated art museum inside the hotel! There’s also a fitness center, as well as The Atrium, a sun-filled private lounge on the upper floors. Hotel on North also hosts a restaurant and is a pet-friendly hotel. Book Hotel on North here.

And if you’re looking to stay in one of the North County Berkshire towns, check out Hotel Downstreet in North Adams. This is the only hotel in North Adams on Main Street and you’re only steps away from some of the amazing things to do in this town.

The location is great and they offer spacious rooms with an art focus. Since you’re in such a culturally rich region of the United States, it’s only fitting that there are also galleries located on the first floor of the hotel too. There’s also an indoor pool and hot tub on the lower level, which has a fun mural painted down there.

We stayed here on our second visit to the Berkshires and really enjoyed the location as we were such a short distance away to soo many cultural institutions and Berkshires attractions. Book Hotel Downstreet here.

Best Towns & Places to Visit in the Berkshires (Post Summary):

Pittsfield is the largest town in the Berkshires, known for its vibrant arts scene, historic architecture, outdoor recreational opportunities, and cultural attractions such as the Berkshire Museum and Barrington Stage Company.

The best town to stay in the Berkshires to explore the region is Pittsfield since it’s in the center of the Berkshires. Another popular town to stay in is Lenox, which is famous for its hotels and resorts in Gilded Age Mansions. North Adams is also an excellent choice and pick for best towns to stay in the Berkshires as it’s one of the most charming downtowns.

The Real Housewives of New York stayed at the Blue Stone Manor in the Berkshires town of Great Barrington.

The Berkshires are famous for their stunning natural beauty, cultural institutions like Tanglewood and Jacob’s Pillow, thriving arts scene, historic sites, and as a popular destination for outdoor activities and scenic drives.

The best time of year to visit the Berkshires is from June to August when there’s pleasant weather for outdoor activities as well as when many of the performing arts festivals and programs take place. Fall is also considered the best time to visit the Berkshires due to the gorgeous New England fall foliage lanscapes.

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Home » Travel Guides » United Kingdom » England » 15 Best Places to Visit in Berkshire (England)

15 Best Places to Visit in Berkshire (England)

One of the Home Counties, Berkshire’s bucolic rural scenery coupled with being close to London makes it a place where most people will pay handsomely for property.

The county can be extremely fancy, and has been home to royalty since the early 1100s when Windsor Castle was built.

The presence of royalty can be felt in many places, including the distinguished racecourse at Ascot.

And as we work our way through Berkshire you’ll see how much the county’s waterways contribute to its charm.

The Thames meanders west to east, broadening as it goes and nourishing verdant water meadows beside the towns and villages.

The Kennet and Avon Canal was also an important shipping route from the West Country to London, and is now navigated by holidaymakers on barges.

Lets explore the best places to visit in Berkshire :

Two of the most visited attractions in the country are in this regal town on the Thames.

Windsor Castle hardly needs introduction: Since the reign of Henry I in the early 12th century this has been residence for the royal family, which makes it the oldest occupied royal palace in Europe.

You could easily get lost in the 5,000-hectare Great Park, while you can spend a few hours idling around the town, seeing sights like Christopher Wren’s 17th-century Guildhall.

And then for little guys there’s LEGOLAND Windsor, which in 2016 became the UK’s favourite theme park and promises a day of LEGO-themed amusements and rides for kids up to 12.

A well-preserved historic town, the centre of Newbury makes for an agreeable walk, and the grassy tow paths on the Kennet and Avon Canal are wonderfully serene . Newbury Racecourse hosts the Lockinge Stakes in May, one of the most valuable races on the calendar.

The stately home, Highclere Castle is majestic, and is in a sweeping 2,000-hectare estate.

It needs to be part of your plans if you’re a fan of Downton Abbey, as one glance will tell you that this was where the TV show was filmed.

The house is newer than it looks, from the 1800s, and has a “Jacobethan” design inspired by the 16th and 17th-century palaces.

Ramble on the downs in the surrounding country parks, and get to Donnington Castle, where an 18-month siege took place in the English Civil War.

Without knowing about its culinary pedigree, Bray would seem like any other well-to-do and charming village in the South of England.

There are almshouses from the early 1600s and the handsome Church of St Michael, which was constructed in the 1290s and has a lot of riveting medieval artefacts within, including a monumental brass on the tomb of Sir John Foxley.

But Bray’s modern reputation comes from its restaurants, as two of the four three Michelin-starred establishments are in the this village.

The older of the two is the Waterside Inn, founded by the Roux brothers in 1972, while Heston Blumenthal’s Fat Duck has won acclaim for its molecular gastronomy since opening in 1995.

Although it doesn’t get a lot of credit for its looks, Reading is a large and thriving urban centre with a high-ranking university and all the shopping you can handle.

Being close to London it became a manufacturing town in the 1800s and was endowed with perfect transport links, where the Kennet and Avon Canal joins the Thames.

You’re also just a couple of miles east of the North Wessex Downs, with their lush green hills and crystal-clear chalk streams should you crave the countryside.

In the town, poke around the ruins of Reading Abbey and drop by at attractions like the Museum of Zoology, Museum of Berkshire Aviation and the Museum of English Rural Life.

5. Wokingham

In Tudor times Wokingham was a centre for silk spinning, and small hints of this industry remain.

Have a stroll along Rose Street, where the half-timbered houses with taller bottom floors would have contained looms.

The Victorian Gothic revival town hall in the middle of Market Place is still at the heart of the community, with a stylish cafe in its courtyard, and the historic buildings around it house a mix of locally-owned shops and high street brands.

There are a few walks you can begin right in the town, like the path up to Fichampstead Ridges, clad with woodland and heather.

6. Hungerford

Close to Wiltshire in the North Wessex Downs, Hungerford is a little way from Walbury Hill, which at almost 300 metres is the highest point in the Southeast.

The Kennet and Avon Canal curves past the northern side of the town and in the 19th century transported coal and stone quarried from Somerset up towards Reading on the Thames.

Hungerford Wharf is achingly pretty and a wonderful place to see the narrowboats gliding up and down the canal on a sunny day.

Cross the bridge in the town for a taste of southern rural England on the high street, with lots of 17th and 18th century properties, including the Hungerford Arcade, an antiques centre with more than 100 dealers under one roof.

Opposite Windsor on the north bank of the Thames is the town of Eton, synonymous with Eton College.

This is the most famous and prestigious of all of England’s Public Schools, founded by Henry VI and with 19 former British Prime Ministers among its alumni.

If you’re in any doubt about how posh this place is the school has its own Natural History Museum, open on Sundays, but you can arrange a visit at other times.

Eton’s high street has rows of historic brick and half-timbered buildings housing upmarket shops like a delicatessen and antique bookshops, and to stretch your legs there’s lovely green space at the Brocas and South Meadow next to the Thames.

8. Pangbourne

Anybody who recalls the children’s book the “Wind in the Willows” will be interested to learn that its author Kenneth Grahame retired in Pangbourne in the 1920s.

The village is full of handsome old houses with one-off shops, and made all the more picturesque by the Thames.

On the banks are large green water meadows owned by Pangbourne and where the village fete takes place every June.

For the rest of the summer they’re a dreamy spot for a picnic in the shade of the willow trees.

If you’re travelling with little ones they’ll have a fun time at Beale Park, a gentle attraction with farm animals and more exotic species like meerkats, lemurs and mongooses.

The three villages that make up the town of Ascot are very well-heeled and are mostly geared towards Ascot Racecourse, which is surely the most prestigious in the country.

So for visitors who show up for the 26 days of racing each year in need of accommodation there are plenty of hotels and restaurants.

The course has close links to the royal family, having been established by Queen Anne in 1711 and  is situated just a few miles from Windsor.

Royal Ascot Week in June remains wildly popular, packing in 300,000 spectators and attended without fail by Queen Elizabeth.

Since the 18th century this event has been a mainstay of the “London Season” for the country’s social elite.

10. Streatley

At an ancient crossing on the Thames, Streatley is a stunning village right next to the larger town of Goring, across the county line in South Oxfordshire.

The landscape is one of steep wooded hills that are outcrops of the Chiltern Range on the eastern cusp of the North Wessex downs.

A lot of the surrounding countryside is owned by the National Trust so you’re free to walk up and admire of the views of the river and village, while Ridgeway National Trail crosses the Thames at Goring and Streatley on its way east.

In this very upmarket spot you have a fine selection of pubs and restaurants, and there’s also a golf club open to visitors and running since 1895.

11. Maidenhead

The large town of Maidenhead is just across the river from  Buckinghamshire, and links to the neighbouring village of Taplow via the Maidenhead Bridge.

This structure gives us one of the loveliest sights in the town, and was built in the 1770s with seven arches and wrought iron lanterns.

You could walk a small stretch of the Thames Path up to Boulter’s Lock, which is also from the 1700s and is a wonderful spot to sit and ponder the river and its weir, or watch the barges go by.

And between Boulter’s Lock and Bray Lock is the Maidenhead Railway Bridge, designed by the revered Isambard Kingdom Brunel in 1839. The Maidenhead Heritage Centre can clue you in on the town’s connection to the Air Transport Auxiliary, which was based near the town in the Second World War and helped move vital RAF machinery around the country.

12. Cookham

One of Britain’s most acclaimed 20th-century painters, Stanley Spencer was born in this Thameside village where he also spent a great deal of his life.

Now in the Wesleyan Chapel that he attended when he was growing up there’s a museum with more than 100 of Spencer’s paintings and drawings.

Give yourself time to see a bit more of the village and its common, where there a blend of timber-framed houses and adorable cottages with flint walls.

You’ll be looking at some of the most expensive property per square-metre in England, in what is often described as the richest village in the country.

13. Kintbury

In the green rolling hills of the North Wessex Downs, the small waterside village of Kintbury polls among the best villages in the country.

You won’t be blown away by any amazing sights, but can see rural England at its primmest in one of the most coveted addresses around.

On the high street the older part of the village looks much as it did a century ago, with delightful brick cottages and a rustic medieval church.

Stop at the 18th-century Dundas Arms next to the Kennet and Avon Canal for a pub lunch with a gentrified twist.

14. Sulhamstead

Another understated pick for an excursion, Sulhamstead does have one high-profile visitor attraction in the Thames Valley Police Museum.

You can just show up on a Wednesday, and on other days of the week you’ll need to phone ahead.

But if you’re fascinated by one of 20th century Britain’s most notorious heist’s, this museum in a beautiful neoclassical mansion has artefacts relating to the Great Train Robbery in 1963. On the Kennet and Avon Canal is the endearing Tyle Mill, which was originally for flour and later became a sawmill, loading and shipping timber with the help of the wharf.

Just up from Eton and Windsor, this workmanlike town doesn’t have the same reputation for history and architecture; rather it’s a place of business and industry that complements the more genteel places nearby.

The bricks for Eton College were baked in Slough, and the Industrial Estate remains a hive of activity and a base for international companies like LEGO and McAfee.

People head to the centre for the Observatory Shopping Mall, which has 120 stores, and Slough is right by the Colne Valley Regional Park, a large, mostly undeveloped space that acts as a green buffer around the M25.

15 Best Places to Visit in Berkshire (England):

• Sulhamstead

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With so many places to visit in Berkshire, you can easily forget you're right on London’s doorstep. Just 45 minutes by train from London, you'll discover a wealth of towns, villages and countryside to explore, making this county the perfect antidote to UK city life.  A county with unique connections to the British Royal Family, where you will find the River Thames meandering along its northern edge and beautiful parks and gardens ablaze with colour. 

The North Wessex Downs (AONB) to the west of the county, a rich mosaic of chalk habitat, woodland, pastures and common land and the world famous historic town of Windsor to the east.  You'll find a year round events calendar, along with vibrant riverside towns of Reading and Maidenhead, the famous college of Eton and the place where the historic Magna Carta was signed.  Today this romantic county offers the perfect escape from the everyday, combining royal heritage, a slice of luxury with the great outdoors.  To get the most out of your stay, start planning your days out in Berkshire here.

Visit Berkshire

Windsor , Berkshire, the weekend home of the British Royal family, home to the iconic Windsor Castle, the world famous long walk and the beautiful Windsor Great Park.  With history and heritage at every turn, beautiful parks and gardens, riverside walks and great shopping, this beautiful historic town makes for a great South East short break destination.

Berkshire is the birthplace of the Duchess of Cambridge, Kate Middleton, raised in the quaint village of Buckleberry where her parents’ home is still located today. It was in the village of Pangbourne in Berkshire where she spent her school days at St Andrew’s School. Situated on the River Thames, Pangbourne has been cited as the inspiration of many famous authors’ novels including Kenneth Grahame and Jerome K. Jerome.  Full of character, Pangbourne is a great place to visit.

Vibrant Reading , Berkshire, a modern destination with a medieval history, packed full of in or on the water activities, adrenaline fuled attractions, rich history and great places to stay.  Located on the River Thames it is home to the 900 year old Reading Abbey ruins, the Reading Festival, and the departure point for modern pilgrims and walkers retracing the steps of medieval pilgrims along St James’ Way to Southampton.  

Berkshire is also home to many other picturesque towns and villages such as  Newbury , Hungerford ,  Ascot , Hurley, Cookham, Bray, Littlewick Green, and Waltham St Lawrence. Find out more about towns and villages in the county with our interactive map of Berkshire .

Things to do in Berkshire this weekend

Many of Berkshire's tourist attractions are open all year round so find the best days out in Berkshire with activities listings each showing a map and opening times for your convenience. Or why not browse our Berkshire events guide to find out what's on this week.

Top 10 things to do in Berkshire

For things to do in Reading, Newbury, Maidenhead , Bracknell and other Berkshire towns, browse our pick of the best attractions below or find a more comprehensive list of what to do and places to visit at the bottom of the page.

• The Savill Garden , Windsor
• Windsor Castle and the Changing of the Guard , Windsor
• Thames Rivercruise Boat Trips , Caversham
• Kennet Horse Boat Company , Hungerford
• Kris Cruises , Slough
• Newbury Racecourse , Newbury
• Norden Farm Centre for the Arts , Maidenhead
• The Coconut Tree , Reading
• Ascot Racecourse , Windsor
• Museum of Rural Life , Reading

List of things to do & places to visit for days out in Berkshire

For more about Berkshire, including ideas on days out, where to stay and things to do in Berkshire, browse through the below selection of attractions and towns and villages that collectively make Berkshire such a memorable destination to visit. Use the 'map view' button to find something near you.

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Streatley-on-Thames

The village of Streatley-on-Thames stands on the opposite side of the River Thames to Goring; Oxfordshire on one side and West Berkshire on the other, linked by a bridge which was built in 1923

St Thomas' Church

Church / Chapel

Alabaster nobles and wall paintings in a rural idyll.

This simple little church, with pre-Norman origins, stands in an idyllic spot beside a water meadow next to the River Lambourn.

Its village has long since vanished, but the spirit of the…

Holme Grange Craft Village

Craft Centre

We offer a wide range of goods and services and a fabulous tea shop in a historic barn opening onto a beautiful enclosed courtyard where you can sit and relax while you enjoy your refreshment.

Waltham St Lawrence

One of the most westerly parishes in the borough, Waltham St Lawrence includes the hamlets of West End and Shurlock Row and contains many fine examples of domestic architecture.

The village is centred on its cattle pound, around which are many…

Norden Farm Centre for the Arts

Gigs, comedy, film, theatre, gallery, classes, cafe bar. Since September 2000, Norden Farm has offered the people of the Royal Borough of Windsor and Maidenhead, and beyond, the best in entertainment and the performing arts.

Despite much modern development, Datchet still manages to retain many features of the quiet riverside settlement it once was. The older buildings cluster around The Green with its central oak tree commemorating Queen Victoria’s Jubilee.

Greenham and Crookham Common

Nature Reserve

After many years as a military site, Greenham and Crookham Common has been restored and reopened to the public. The area is a Site of Special Scientific Interest (SSSI) and cattle and Exmoor ponies graze here.

What's happening in Newbury?

Set along the banks of the River Kennet and the Kennet and Avon Canal, Newbury has a fresh, rural atmosphere combined with great shopping facilities and new attractions.

Thatcham is a town in the historic county of Berkshire and is situated just three miles east of Newbury.

While the magnificent Windsor Castle is this majestic town's main attraction, don't miss the tranquil Savill Garden, or the family-friendly Legoland just a short drive away.

Windsor Road, Egham

Runnymede is famous for its monuments, the most famous being the one to commemorate the Magna Carta. The area is a riverside setting of meadows, grassland and woodland with a network of pleasant paths and pleasure gardens.

Sunninghill

Sunninghill means 'the home of Sunna’s people'. Most of the development around the large country houses of the 18th century was accelerated by the discovery of health-giving salt springs and rapidly increased with the advent of the railway in 1841.…

Earley is a town and civil parish in the English county of Berkshire and lies some 2 miles  south and east of central Reading.

Changing the Guard

Sightseeing

The Changing of the Guard is one of the highlights of a visit to Windsor. A band usually accompanies the Guards, although this is subject to weather conditions.

The Guards can be watched as they march up the High Street and into the Castle, but…

Pretty riverside Hurley lies halfway between London and Oxford, being 55 miles from each by river. The river has always been an important part of the village’s history with records of a ford as early as the 6th century.

Cobbs Farm Shop

Cobbs was founded out of a passion for supplying quality food with provenance to our customers as well as providing a platform to the immense volume of artisanal producers on our doorstep. You will find a fantastic farm shop, delicatessen, butchery,…

The Kennedy Memorial at Runnymede

Historic Site

Set in a symbolic acre of land donated to the United States of America by Queen Elizabeth II in 1965, this seven tonne block of Portland stone commemorates the life of President John F Kennedy following his tragic assassination.

Kennet Horse Boat Company Ltd

Traditional horse-drawn and motorised canal boats. Kennet and Avon Canal. Refreshments, coach parking. Suitable for all age groups.

Despite the rather unfortunate Saxon meaning of its name, Hor-tun or 'Dirty Farm', the village today is a clean and wholesome place clustered around its small triangular green, but with more modern houses on the roads to Wraysbury and Colnbrook.The…

The Reading Room

Opened in 2020, The Reading Room at the Roseate Hotel Reading  offers delicious modern cuisine revolving around the freshest, seasonal ingredients and best of British produce from Executive Chef Rajesh Maharjan.

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The 7 Best Towns to Visit in the Berkshires

Our travel recommendations are based on personal experiences and research.

Seven of the best and most popular towns in the Berkshires to visit. Add these to your itinerary to experience the best of what the region has to offer.

You’ve heard the Berkshires are a spectacular region in Massachusetts – full of natural beauty, art, culture, and quaint New England towns.

But you’re probably wondering which Berkshires towns are worth visiting.

Nearly every stretch of this westernmost Massachusetts county is stunning, with rolling hills and charming villages sprinkled throughout.

But a few Berkshire towns stand out – not only for their aesthetic beauty but for what they have to offer within them.

Below, we share the seven best Berkshires towns to focus your itinerary on when you visit. But before we start, let’s get better acquainted with this area.

Where are the Berkshires?

In the United States, the Berkshires are the westernmost county in Massachusetts.

To the north, Berkshire County borders Vermont. To the west it borders New York State, and to the south, Connecticut.

The region to the east of the Berkshires is known as Pioneer Valley, a portion of the Connecticut River Valley. It consists of the Massachusetts counties of Hampden, Hampshire, and Franklin.

Like most other governmental counties in Massachusetts, Berkshire County has no active legal governmental or legal function. It only serves as a historical geographic region except for certain offices such as sheriff and registry of deeds.

The U.S. Berkshires are named after Berkshire County in southern England, the former home county of Sir Francis Bernard, who served as the royal governor of Massachusetts from 1760-1769 and named the county.

While the written name, Berkshire, is the same in both countries, the British pronounce it Bark-sheer while Americans say Berk-sheer .

A Map of the Berkshires

This map illustrates where the Berkshires are in relation to the rest of Massachusetts. It also highlights the location of the seven best towns to visit in the county.

What are the Berkshires known for?

First and foremost, the Berkshires are known for its natural beauty.

Western Massachusetts is known for its gently rolling hills that, while less dramatic than the mountain ranges of Vermont or New Hampshire, still feature wide-sweeping, dramatic vistas that come alive with vibrant color in fall.

From this backdrop, you’ll find some of the most charming villages in New England – another characteristic of the Berkshires. Each community showcases an assortment of architectural styles and time periods, reminiscent of previous eras gone by.

The picturesque setting of the Berkshires inspired wealthy families in the late 19th and early 20th century, a time known as the Gilded Age, to make the Berkshires their late summer retreat. Today, the legacy of these opulent mansions and gardens lives on in the form of museums and tourist destinations.

While an art community existed before the Gilded Age, during this period, the Berkshires also became known as a destination for artists and art lovers alike. An influx of wealth brought with it support for the arts, and this small region boasts an oversized number of impressive museums, performing arts venues, and is the summer home of the Boston Symphony Orchestra.

Today, former city dwellers from New York and Boston in particular, have made the Berkshires their home. With them, or among them, has come an influx of culinary expertise resulting in exquisite farm-to-table restaurants, cozy cafes, and several food coops and farmer’s markets.

To summarize, the Berkshires are known for:

• Gorgeous rolling green hills in the summer that showcase vibrant foliage in the fall.
• Art, art, and more art – of all mediums, venues, and variety.
• Quaint New England towns that harken to previous eras.
• Opulent Gilded Age mansions once referred to as summer “cottages”
• Fantastic hiking opportunities with panoramic views that go on for miles
• A foodie culture of outstanding farm-to-table restaurants and cafes

The best towns in the Berkshires to visit

You’ll find beauty around every corner of the Berkshires, but a few towns in particular draw the most visitors each year. These communities have well-regarded cultural attractions, shopping, restaurants & cafes, and the most popular hiking spots or outdoor recreation.

Listed by popularity (with our preference mixed in), here are the seven best Berkshire towns to explore when visiting.

Nearly anyone who has spent a small amount of time in the Berkshires has most likely visited Lenox.

Located just south of central Berkshire County, this community is where wealthy industrialists primarily set up their summer homes during the Gilded Age. This influx of cash during the late 18th and early 19th centuries not only developed Lenox’s cultural and artistic center but also put it on the map as a popular tourist destination.

While Lenox’s small downtown is walkable and full of art galleries, high-end clothing boutiques, cafes, restaurants, and a bookstore, the village is most well known for its cultural attractions, including the Tanglewood Music Center, Edith Wharton’s historic home, The Mount , and the historic Ventfort Hall Mansion & Gilded Age Museum , among others.

See related: Top 15 Best Things to Do in Lenox Massachusetts

Great Barrington

Great Barrington is often considered the second most popular town to visit in the Berkshires.

Unlike Lenox, which has more of an old-money vibe, Great Barrington is a mix of Brooklynites, locals, and former hippies. Wandering through the downtown, you’ll find high-end clothing stores, art, gifts, and housewares – on par with what you’d find in urban retail establishments.

The hippie vibe can be seen in rainbow-painted crosswalks, the well-stocked Berkshire Food Co-op , and an outsized number of cannabis dispensaries. High-end restaurants also line Main and Railroad Streets, as do cafes, coffee shops, and a local ice cream shop.

Hiking enthusiasts will also want to check out Monument Mountain ‘s trails. This mountain, the name of which is derived from Mohican tribe stone offerings, is also tied to Herman Melville, William Cullen Bryant, and Nathaniel Hawthorne.

See related: Top 15 Best Things to Do in Great Barrington Massachusetts

Williamstown

Williamstown is most definitely among the best Berkshire towns to visit.

This small community has it all – with its definitive New England college campus, a red brick building downtown, world-class art museums, and excellent hiking opportunities – all set against stunning rolling hills in the backdrop.

Art lovers, in particular, will enjoy a visit here with The Clark and Williams College of Art Museum exhibiting works from celebrated artists such as Pierre-Auguste Renoir, Sandro Botticelli, Claude Monet, Edgar Degas, John Singer Sargent, Edward Hopper, Winslow Homer, and contemporary artists, to name a few.

And hiking enthusiasts will want to check out the magnificent Mount Greylock , the highest peak in Massachusetts. Views from the top of Mount Greylock stretch as far as 90 miles in the distance. And a variety of hiking trails are suitable for both novice and experienced hikers.

Simply strolling through the Williams College campus and the small downtown area is a delight. Although you won’t find as many high-end stores here as you would in Lenox or Great Barrington, the selection is still alluring. A few casual restaurants and an ever-popular coffee house round out the downtown’s appeal.

See related: Top 15 Best Things to Do in Williamstown Massachusetts

Stockbridge

Nestled between Lenox to the north and Great Barrington to the south, Stockbridge is another popular town to visit in the Berkshires.

The biggest attraction in Stockbridge is the museum dedicated to Norman Rockwell , the painter and illustrator known for his heartwarming and nostalgic depictions of everyday life in the 20th-century U.S.. Here, you’ll find hundreds of his renowned Saturday Evening Post covers and numerous paintings, including a portrait of J.F.K. and Rockwell’s Four Freedoms series.

Stockbridge’s tiny downtown is also worth a visit, whether it’s to admire the delightful historic buildings captured in Norman Rockwell’s Main Street Stockbridge painting, wander into a few shops or art galleries, or grab a bite to eat at the Main Street Cafe.

You’ll also want to carve out time to tour Naumkeag , a stunning Gilded Age mansion a short distance from downtown. And serious art enthusiasts will want to visit Chesterwood , the house of Daniel Chester French, the sculptor of the statue of Abraham Lincoln at the Lincoln Memorial in Washington, D.C.

See related: Top 15 Best Things to Do in Stockbridge Massachusetts

West Stockbridge

West Stockbridge isn’t as well-known as the previously mentioned towns, but this sweet community is worth a stop.

One of the central points in town is No. 6 Depot & Cafe , serving some of the best coffee you’ve ever tasted. Located in a former train station, this roastery and cafe is a community hub where friends, families, and coworkers meet over a latte or espresso.

On Main Street, a short distance away, you’ll also find some interesting art galleries, a Shaker furniture store, an antique gallery, a used bookstore, and the Public Market – a good place to pick up a sandwich and drink.

If you’re up for an artistic adventure, stop by TurnPark Art Space’s sculpture park on Moscow Street. Donations of $10 are requested for a self-guided tour of the property.

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North Adams

A former mill town, North Adams is almost double the population of neighboring Williamstown and still a little rough around the edges after the collapse of his industrial center. But undoubtedly, North Adams is worth a visit – especially if your itinerary includes the north of Berkshire County.

Mass MoCA , the largest contemporary art museum in the United States if not the world, is the largest draw in North Adams. Here, you’ll experience art like never before. Housed in an interconnected array of spacious former fabric mills, Mass MoCA allows artists to show works unbounded by the restrictions of traditional museums. Popular exhibits at Mass MoCA include Sol LeWitt’s  Wall Drawing Retrospective  and James Turrell’s  Into the Light  collection.

After visiting the museum, grab a bite to eat in one of the handful of eateries on the property or head downtown for a meal at Public Eat + Drink. If North Adams is the last stop on your trip and you’re heading back east, follow the Mohawk Trail and capture the view from the famous hairpin turn lookout as you leave the city.

As the largest city in the Berkshires and its centralmost point, Pittsfield is a common stop for anyone traveling throughout the county.

While downtown Pittsfield is still up-and-coming, the city has several cultural attractions. First, there’s the Berkshire Museum , which is an aquarium, natural history, and art museum in one and a great destination for families with children.

Another popular destination in Pittsfield is the Hancock Shaker Village – a living history museum showcasing Shaker architecture, lifestyle, and culture, including 20 buildings and multiple acres of gardens and walking trails.

Downtown, you’ll also find a few art galleries and studios, a performing arts theater, and restaurants & cafes. There’s also a teen-run Farmer’s Market held on Saturdays during warm-weather months.

See related: Top 15 Best Things to Do in Pittsfield Massachusetts

How to decide which Berkshire towns to visit

While ideally, you’ll visit all seven Berkshire towns on your trip, not every itinerary allows for such an extensive overview of the region. Given your interests and desired activity, here’s a breakdown of which Berkshire towns are best for you.

If shopping and spending time in restaurants and cafes is at the top of your list, visit Great Barrington. While this downtown is small and certainly walkable, there are a variety of well-appointed retail and culinary options to choose from here.

Museum goers and those interested in visiting Gilded Age mansions will want to spend time in Stockbridge and Lenox. These communities have a plethora of art museums, performing arts venues, and the famous Tanglewood, the summer home of the Boston Symphony Orchestra. There are also a handful of mansions in these towns that serve either as museums or hotels.

Art lovers – particularly those interested in world-class artists and contemporary art – will want to carve out time to visit Williamstown and North Adams. While these communities are a bit far from Lenox and Stockbridge, they pair well by rounding out the art viewing options in the area. A stop at the Berkshire Museum in Pittsfield is also a welcome attraction while traveling between these two areas.

And finally, if hiking or outdoor recreation is high on your list of things to do, nearly every community on this list has much to offer. While spectacular views can be seen from nearly every hill or mountain climb in the Berkshires, it’s worth noting that the climbs get steeper and the views more extensive the further north you travel in the county.

See related:

Top 35 Best Things to Do in the Berkshires

The 10 Best Museums to Visit in the Berkshires

10 New England Small Towns Like Stars Hollow

( As a GetYourGuide affiliate, I earn from qualifying purchases at no extra cost to you. )

About Kerry Flatley

Kerry Flatley has lived in New England for the past 26 years. She has roots in Maine & Massachusetts, family in New Hampshire, and grew up close to the Connecticut border. She loves all that this region has to offer – the ocean, mountains, islands, history, villages, and cities. When she’s not writing about New England, she’s relaxing at home in the Boston suburbs with her two teenage daughters and husband.

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15 Best Things to Do in the Berkshires

From craft brews to cultural hot spots, this beautiful region of Massachusetts has it all.

The Berkshires, a rural mountain region in western Massachusetts, draws countless visitors every year thanks to its fascinating history, ample outdoor activities, burgeoning food scene, and incredible shopping. The area's charming towns, including Lenox, Stockbridge, and Great Barrington, offer a surprising number of activities for every type of traveler.

Culture seekers will appreciate the Norman Rockwell Museum and the Tanglewood music venue, while nature lovers will find no shortage of trails with spectacular views. Whether you're in the mood for history or craft beer, here are some of the best things to do in the Berkshires, no matter the season.

Catch a concert at Tanglewood.

This open-air music venue in Stockbridge serves as the summer home of the Boston Symphony Orchestra. While the lush grounds and expansive lawns are open all year round (free of charge), you'll want to plan your trip during the summertime, when you can listen to music under the stars. (Bringing along a delicious dinner and cozy blanket is highly recommended.) Event programming is always rotating , but previous acts include performances from Ringo Starr & His All-Starr Band, James Taylor, the Juilliard String Quartet, and The Black Crowes, to name a few.

Go shopping in Lenox.

Lenox is famous for its charming downtown area dotted with eclectic boutiques and one-of-a-kind shops. Pick up some unique home goods at Annie Selke Shop, Design Menagerie , or MacKimmie Co. ; add to your wardrobe with staples from Catwalk Boutique , or Purple Plume ; or grab some vacation reading material (and enjoy a glass of vino) at The Bookstore & Get Lit Wine Bar . Meanwhile, gourmands can peruse the aisles of Oliva Gourmet Olive Oils & Vinegars and Dare Bottleshop & Provisions .

Hike Mount Greylock.

At nearly 3,500 feet tall, Mount Greylock is the highest point in the state of Massachusetts. The entire Mount Greylock State Reservation spans around 12,000 acres and boasts several hiking trails, including a stretch of the famous Appalachian Trail. At the summit, visitors can stop at the Veterans War Memorial Tower, a 93-foot granite lighthouse with 89 steps leading to an observation deck. From there, enjoy panoramic views stretching across five states (Massachusetts, New York, Connecticut, Vermont, and New Hampshire).

Eat your way through Great Barrington.

The streets of Great Barrington are lined with tasty restaurants that'll satisfy a range of cravings. Keep it casual at Baba Louie's , famous for its selection of sourdough pizzas. For authentic Mexican staples like mole and margaritas, head straight to Xicohtencatl , which occupies a striking yellow house with a sprawling porch. Prairie Whale is a dinner-only haunt known for its rustic-chic aesthetic, lively ambience, elevated American entrees featuring locally sourced ingredients, and creative cocktails. For a true treat, make a reservation at Number Ten , which serves up all sorts of steaks, poultry, and seafood, plus mouthwatering sides like creamed spinach, mac and cheese, and mashed potatoes.

Check out the Norman Rockwell Museum.

Founded in 1969, the Norman Rockwell Museum in Stockbridge boasts an expansive selection of the artist's work — almost 1,000 original paintings and drawings, to be exact. (Rockwell lived in the town from 1953 until 1978, when he died.) The 36-acre campus is home to 10 galleries, the artist's beloved Stockbridge studio (which was moved here in 1986), and an impressive collection of 100,000-plus items that range from personal calendars to fan mail.

Embark on your own dessert trail.

Grab a sweet treat (or three) at one of the many dessert spots in and around the Berkshires. In Pittsfield, indulge in some summertime soft serve at Dairy Cone . Then, make your way to Lenox to check out the seasonal Sweet Dreams cafe, which sells crowd-pleasing pastries like cinnamon buns and chocolate chip cookies, or the beloved Chocolate Springs Cafe for specially crafted confections like truffles, chocolate-covered pretzels, and marshmallows. Candy lovers of all ages will also appreciate the nostalgia-inducing Robin's Candy , a Great Barrington shop stocked with a curated collection of sweets to suit every palate. Another nearby favorite is the Parisian-inspired Pixie Boulangerie .

Travel back in time at Hancock Shaker Village.

Learn more about Shaker history at Hancock Shaker Village , which dates back to the late 1700s. Today, the site has been transformed into a living history museum with a working farm, a one-mile walking trail, and thousands of fascinating artifacts (think: furniture, tools, textiles, and more). It's also worth noting that Hancock Shaker Village is open seasonally (typically from mid-April through October), so plan your visit accordingly.

Get out on the lakes.

Lauren Breedlove/Travel + Leisure

The Berkshires is home to dozens of pristine lakes for swimming, paddling, boating, and fishing. The 511-acre Pontoosuc Lake is among the region's most scenic, and its bright blue waters make it a popular spot for boating. Pack a picnic lunch, some towels, and a chair to lounge on the grassy lawns along the shore. With the Berkshires being one of the best fall vacation destinations , it's no surprise the lake is also a must-visit for foliage views when the surrounding trees turn fiery red, orange, and yellow. Meanwhile, Lake Onota is slightly larger at 617 acres. Here, you can relax along the sandy beach area before heading into the water to swim, kayak, or canoe.

Wander through Mass MoCA.

The Massachusetts Museum of Contemporary Art (Mass MoCA) in North Adams offers a whopping 250,000 square feet of gallery space, so be sure to carve out enough time to explore it all. Expect to be dazzled by an array of extravagant masterpieces, including eye-catching ceramics, interactive exhibitions complete with lights and sounds, larger-than-life wall drawings, and striking sculptures.

Get a taste of everything at the Berkshire Museum.

Barry Winiker/Getty Images

Get a little more culture during your visit with a stop at the Berkshire Museum in Pittsfield. Here, guests can explore the museum's vast and varied collection of more than 40,000 objects in its exhibits and at community events. According to the museum's website, its founder, Zenas Crane, was inspired by the American Museum of Natural History, the Smithsonian, and the Metropolitan Museum of Art, and decided to combine all their best attributes into one space. Thus, the Berkshire Museum makes it possible to see fine art, natural science, and history exhibits under one roof. 

Indulge your bibliophile dreams at Edith Wharton's The Mount.

Courtesy of The Mount

One of the best things to do in the Berkshires is visit  The Mount , the former home of author Edith Wharton, who wrote books like "The Age of Innocence" and "The House of Mirth." The property is now a National Historic Landmark and cultural center dedicated to preserving the space and her legacy. Guests can come to tour the gardens, the home's interiors, and a rotating list of exhibits showcasing both literature and life during the early 20th century. Visitors can even come for a quick ghost tour of the property — if they dare.

Pluck the perfect apple at Hilltop Orchards.

Courtesy of Hilltop Orchards 

Participate in one of the area's favorite fall pastimes — apple picking — with a visit to  Hilltop Orchards . The farm, located just on the edge of the Massachusetts and New York border, has been a Berkshire institution for more than a century. Guests can pick (and eat) 27 different apple varieties come fall and indulge in a sweet cider donut, too. Not visiting the area during the autumn? No problem — the orchard is open year-round and offers cidery tours and tastings, as well as access to its trail system, spread across the 200-acre grounds, which are ideal for hiking in the spring, summer, and fall, and snowshoeing all winter long.

Seek out more art at The Clark Art Institute. 

Another stellar cultural institution in the Berkshires,  The Clark Art Institute has been open to the public since 1955 and has a dual purpose. In addition to preserving the classics as a museum, it's also a research center dedicated to higher education and expanding the public understanding of art. Come explore its permanent and rotating exhibitions, which have spotlighted international artists such as Edvard Munch and Pierre-Auguste Renoir. If you have some extra time, don't forget to marvel at its spectacular 140-acre campus grounds, too. 

Take a ride at the Berkshire Scenic Railway Museum.

Courtesy of Berkshire Scenic Railway Museum

Weave your way through some of the area's most beautiful landscapes with a ride on a historic railway. The Berkshire Scenic Railway Museum , founded in Lenox in 1984, aims to preserve the railway and its history by maintaining historical data and equipment. It also offers visitors the chance to hop aboard for fun seasonal rides. Excursions include a fall foliage trip, a winter Santa train, and more. Check out the railway's website to see what's available when you visit. 

Toast to a successful trip.

Cap off a fun-filled trip at one of the nearby breweries, wineries, or cideries. Oenophiles will especially appreciate Balderdash Cellars , where you can lounge on a lawn overlooking a lake. For craft brews, make your way to Wandering Star Craft Brewery , Berkshire Brewing Company , or Big Elm Brewing . Alternatively, if you prefer cider, look no further than the Berkshire Cider Project .

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The Berkshires

Choose your own adventure.

Serene mountain vistas, lush forests, and clear blue lakes define the Berkshire landscape, an idyllic setting for your next family vacation, romantic escape, or weekend with friends. Boasting more than 100 world class cultural attractions, superior outdoor recreation, and a famous farm-to-table food scene, the Berkshires promises an unforgettable experience.

Come Play in the Berkshires

All Aboard the Berkshire Flyer

Skip the Thruway and take the view way to the Berkshires this summer. The Berkshire Flyer provides seasonal rail service from New York City to the Berkshires each weekend from June 21st through Labor Day. And the Berkshire Flyer now includes train service from New York City to Pittsfield on Sunday mornings!

Discover Berkshire Stages

Renowned as an artistic playground for creatives of all kinds, you’re guaranteed all the feels when you traverse the stages along this performing arts trail.

Play Outdoors

Everyone living in or visiting the Berkshires is invited to find their next adventure at the NEW BerkshiresOutside.org site. Discover over 550 locations across the county.

Hit the Biking Trails

Biking is a great way to experience the beauty of the region. Challenge yourself on winding through forests or meander leisurely along scenic rail trails.

Picture yourself in the Berkshires

ArtWeek Berkshires

One way to ensure vibrancy regardless of fickle weather is to experience ArtWeek Berkshires, a county-wide celebration of all things creative by local artists. The annual 10-day event has moved permanently from fall to spring - this year the festival takes place May 17-27, 2024.

Plan Your Visit

Inspire wanderlust with the Official Guide to the Berkshires, a year round, comprehensive resource to help you plan your perfect getaway.

Visit in Spring

Spring is a glorious season in the Berkshires, a time of renewal and rejuvenation cast in buttery sunshine.

Explore the Berkshires

Use the Berkshire Brochure to explore by north, central, and south. Includes insider tips, must-visits, and more!

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Places To Visit In the Berkshires, Where Culture Meets Nature

Planning a road trip in the Berkshires, nestled in bucolic western Massachusetts? This is the ultimate guide to all the best places to visit in the Berkshires. It covers the must visit towns, cities, parks, museums, and landmarks.

The Berkshires are a lovely area, almost ripped from paintings at a museum. The Berkshires are dusted with magic, and the perfect place for a New England road trip .

The region evokes an earlier America, with houses and architecture straight from a Norman Rockwell painting.

The Berkshires is a laid back region, quietly unbuttoned without the glitz or cocktail party circuit. The area was made famous by literary figures escaping the city to their turn of the century castle-cottages, set under solitary starry nights.

The Berkshires are full of winding roads with undulating meadows, deep green ellipses of hills, organic farms, and trees ablaze in autumn.

But it’s definitely not just for nature lovers and leaf peepers. The Berkshires are a unique confluence of nature, historic landmarks, cultural gems, and vaunted museums.

In fact, the Berkshires are New England’s premiere summer region for culture-driven travel and road trips. Wherever you go, you’ll be confronted with the choice: art or the great outdoors?

Despite its rural setting, the Berkshires also have a hot foodie scene, with a hip farm to table vibe. In the Berkshires, restaurant owners source food locally from innovative farmers, grow their own herbs and micro-greens, and raise hens.

How Long Should You Spend in the Berkshires?

It depends. You could spend a busy weekend or a laid back week on a road trip through the Berkshires region. Each new mile yields new discoveries. If you’re coming from Boston or New York City, budget 3 hours of driving each way.

If you’re embarking on a weekend getaway, use my list of must see destinations and towns to pick and choose the places that most appeal to you in the Berkshires.

The Berkshires are small enough that you can base in one part and explore the whole region. If you want one base, choose Lenox or Stockbridge.

They’re the prettiest towns, looking exactly as you’d imagine a classic New England village. Both have amazing cultural, culinary, and outdoor options. They’re centrally located and within easy striking distance of the other must see sites in the Berkshires.

If you want two bases to explore the region in depth, pick North Adams in the north and Stockbridge in the south.

When Should You Go To the Berkshires?

The Berkshires are evolving into a year round destination. Summer is the busiest time in the Berkshires, when people are looking to ditch the bustling city for quieter climes.

If you’re looking to attend concerts, shows, and events, aim for summer. Be sure to book festival and theater tickets in advance.

Fall is gorgeous, but also quite busy. The brilliant foliage and pleasant weather also make fall an idea time to take a fall foliage road trip in New England . In the Berkshires, the foliage typically reaches its peak in mid October.

How To Get To the Berkshires

You really need a car to visit the Berkshires. Everything requires driving. Even if you base in a town like Stockbridge, you need to drive to the local attractions.

Most people drive to the Berkshires. Depending on where you base, it’s about a 2:15-2:45 drive from Boston and a 2:45-3:15 drive from New York City.

If you’re flying to the Berkshires, the closest major airport is in Albany, about a 45 minute drive from Stockbridge. There are also bus and train connections to Pittsfield.

Places To Visit In The Berkshires

How best to experience the Berkshires’ arts and eats ethos? Here are all the best places to visit in the Berkshires — sites, attractions, and most beautiful towns.

I’ve put them in the likely order you’d visit them on a Berkshires road trip, along with tips on what to see, do, eat, and where to stay in the Berkshires. And, of course, where to get your cultural fix.

Let’s go sniff the mountain air, at least virtually.

1. Great Barrington

For some of the best fall foliage scenery in the Berkshires, take Route 7 and 8 from Great Barrington to North Adams (1:10 hours without stops).

You’ll go past storybook farms, wooden barns, and stone walls. And through the cute towns of Stockbridge, Lee, Lennox, and Pittsfield.

Great Barrington is a town for foodies and antique hunters. It has a fashionable shopping district and excellent restaurants.

Stop in at the the Berkshire Art Gallery, which features a wide range of 19th and 20th century American and European paintings. If you’re a pottery enthusiast, head 12 minutes south of Great Barrington to the nearby Sheffield Pottery.

In terms of outdoor recreation, You can head to Blueberry Hill to pick wild blueberries. For great views and relatively easy hiking, head to Monument Mountain .

Monument Mountain Summit is a 3.8 mile lightly trafficked out and back trail. It features wildflowers, but no views. If you want a vista, you need to sidetrack to Squaw Peak.

Monument Mountain is famously the setting for a double date between authors Herman Melville and Nathaniel Hawthorne. They met and hiked up the mountain. Legend holds that they were caught in a rainstorm during which Hawthorne convinced Melville to write Moby Dick .

• Where to stay in Great Barrington : The Barrington, Thornewood Inn, Granville House
• Where to eat in Great Barrington : Prairie Whale, Rubi’s Cafe, Cheesemongers & Grocers, Meat Market, Bizen, John Andrews, cafeADAM

2. Bash Bish Falls

From Great Barrington detour 12 minutes to Bash Bish Falls in Egremont. Bash Bish is the largest single drop waterfall in Massachusetts and a must see in the Berkshires. Water is sliced in two by a massive boulder creating a picture perfect double waterfall .

At 80 foot high, it’s not Niagara size. But it’s still pretty. A steep 20 minute trail leads from the parking lot.

Bash Bish is on the Massachusetts-New York border. If you want a less challenging hike, drive 1 mile west to the New York side parking lot.

Picturesque Bash Bish Falls has been a popular Berkshires tourist stop since the mid 19th century. When you come upon the falls, you’ll feel as though you’ve discovered a secret, woodland spot. But, be forewarned, there will be many other waterfall pilgrims at this uber popular hiking spot.

3. Stockbridge

Settled in 1734 by British missionaries, Stockbridge may be my favorite adorable small town in the Berkshires. It’s blessed with simple charm and a fabulous line up of cultural attractions.

Three of the greatest American artists and authors called Stockbridge their home — Edna St. Vincent Millay, Herman Melville, and Norman Rockwell. James Taylor sang about the town in Sweet Baby James .

One of America’s greatest treasures is the Norman Rockwell Museum . Rockwell was one of the greatest artists and illustrators in American history. Stockbridge was Rockwell’s long time residence and what he called his “best studio yet.”

His titular museum is home to a year round series of rotating exhibitions of Rockwell’s art and Saturday Evening Post magazine covers. There are 570 Rockwell illustrations, including the famous Triple Self Portrait and Going and Coming .

A permanent exhibit is the quartet called the Four Freedoms , which will seem comfortingly familiar. The most famous of these gems is Freedom From Wont , depicting a family gathering at Thanksgiving.

Rockwell’s studio was painstakingly moved intact to the grounds as well. There, you’ll learn about his creative process.

At Christmas, Stockbridge charms visitors with a re-staging of Rockwell’s painting from McCall’s Magazine, Stockbridge Main Street at Christmas .

You can also visit Chesterwood , the home Daniel Chester House. It’s the 1920s Colonial Revival house, complete with soaring studio, of the legendary sculptor and landscape architect.

Chester created the statue of President Lincoln seated in the Lincoln Memorial in Washington D.C., and you’ll see plaster models in the museum.

The summer estate is beautiful, but it’s Chesterwood’s hiking trails that are acclaimed. Some say that Chester “sculpted the landscape as well.”

After a stroll through the formal gardens, take the easy Woodland Walk carving through the wilder woods. Or, for more of a challenge, try the Ledges Trail with a steep climb to a viewpoint.

Apart from visual arts and historic, the Berkshire Theater Group provides performing arts entertainment. The IS 183 Gallery has a stash of regional and national art works.

Every summer, Stockbridge (along with the town of Lenox) hosts the Tanglewood Music Festival, a series of concerts across all musical disciplines.

Stockbridge is also home to one of the Berkshires Gilded Age “cottages,” Naumkeag . You can tour this quirky 44 room mansion designed by Stanford White, famed starchitect of the time. It boasts original furnishings, rooms full of angles and curves, and captivating gardens.

To get outside in Stockbridge, drive to the end of Park Street and walk through a stone portal into another world, Ice Glen.

You’ll find romantic rugged landscapes, giant tree roots, and massive Ice Age boulders. You’ll need to be fit and agile to hike either the one mile out and back or two mile loop trail.

• Where to stay in Stockbridge : Once Upon a Table, Truc Orient Express
• Where to eat in Stockbridge : The Red Lion Inn, The Inn at Stockbridge

Lenox is a pretty must visit place in the Berkshires. It’s full of art galleries and upscale boutiques housed in historic buildings. It’s probably the priciest place in the Berkshires.

You’ll find the classic Berkshires experience and some of the region’s most iconic properties — Blantyre, Wheatleigh, Canyon Ranch, and The Mount. At one point, there were so many lavish summer homes that Lenox was known as “the inland Newport.”

In 1902, Edith Wharton, the first woman to win the Pulitzer Prize in Literature, built The Mount in Lenox. It was a stately country retreat for the literary lioness and her then-husband, modeled after European manses but lacking their excesses.

No gaudy entries or vulgar grand staircases for the “Lady of Lenox,” who happily lived a corset free life and wrote Ethan Frome and The House of Mirth there. She did most of her writing in her third floor bedroom — in bed!

The Mount has been beautifully restored to its appearance during Wharton’s tenure. The exterior is a striking white stucco, with clusters of gables and white chimneys and a roof capped with a balustrade and a cupola.

Wharton had a lot of style. You might find yourself longing for her furnishings.

Wharton had a pale pink dining room with fuchsia and gold cutlery. The house is a remarkable portrait of how the wealthy lived during this time period. It makes you think about how idyllic surroundings can inspire you as an artist.

The Mount is home to a summer lecture series, weekly bird walks, concerts, theater performances, and outdoor sculpture exhibits. Edith Wharton’s library has been returned to the house, with 22 first editions of her work.

If you want a drink or light meal, head to The Mount’s Terrace Cafe. Then wander in the beautifully landscaped gardens. On Friday Night Fright in September and October, a 2 hour ghost tour traverses the haunted parts of The Mount.

If you like modern art, the Frelinghuysen Morris House & Studio is also worth a Lenox look.

It’s a modernist home exhibiting the works of Suzy Frelinghuysen and George L.K. Morris. It also boasts works by their cubist contemporaries — Pablo Picasso, Juan Gris, and Georges Braque.

For a long walk in the woods, head to nearby Olivia’s Overlook at the center of the Yokun Ridge. The overlook is also the trailhead for several trails varying in length. You’ll have great views, see wildflowers, and the pretty Monks Pond.

• Where to stay in Lenox : Birchwood Inn, Blantyre, Brook farm Inn, Applegate Inn, Devonfield Inn, Gateways Inn and Restaurant
• Where to eat in Lenox : Nudel, Wheatleigh, Bistro Zinc, Alpamayo, Cafe Lucia

5. Pittsfield

While not as quaint as the other Berkshires towns, there are still some things to do that are worth a stop in Pittsfield on your Berkshires itinerary.

The Berkshire Museum has undergone a major renovation. It showcases everything from a stegosaurus to Alexander Calder mobiles.

If you’re a Henry Melville fan, stop in at his small yellow house, Arrowhead . The author lived in this converted warehouse during his most productive years.

He wrote Moby Dick in his second floor study. Melville built his porch on the “wrong” side of the house to better view of Mt. Greylock.

For outdoor fun, 10 minutes down the road is Ashuwillticook Rail Trail. Smack in the middle of two mountains, the 11mile trail is paved for biking, hiking, or cross country skiing.

5 miles southwest of Pittsfield is Hancock Shaker Village , a living slice of American history. It’s a restoration of a religious community that flourished in the 1800s.

The adherents exhibited shaking motions while listening to sermons. You can tour the buildings, including a group dwelling house and stone barn, and watch craftsman at work.

• Where to stay in Pittsfield : Overnight at the excellent choices in Lenox instead
• Where to eat in Pittsfield : Elizabeth’s, Enso Asian Bistro, Mission Bar and Tapas

6. North Adams

30 miles further north lies the quaint town of North Adams. It’s a former manufacturing hub reinvented as a funky cutting edge art town. North Adams is known as “The Town of Steeples and Peaks,” for the spires of its many churches. Come for the art, and stay for the scenery.

Visting North Adams is now one of the best things to do in the Berkshires. Its downtown is filled with art galleries, artists studios, and cute shops. Its pride and joy is Porches Inn, an eye catching row of distinctive multi-colored Victorians.

After meandering the downtown, head straight to the utterly fabulous Massachusetts Museum of Contemporary Art (“MASS MoCA”). Opened in 1999, MoCA is one of the region’s foremost cultural institutions.

MOCA has an emphasis on international contemporary art. The airy industrial campus was expanded in 2017 with new modern buildings by Tadao Ando.

Works are spread out over 250,000 feet in 19 galleries in a renovated 19th century factory, making it the largest contemporary art museum in the US. MoCA is home to exciting works by Louise Bourgeois and Robert Rauschenberg.

Entire walls are decorated by Sol LeWitt. The museum also has a permanent collection with works by the likes of Manet, Constable, Bonnard, Delacroix, Ingres, and Sargent.

In the adjacent town of Adams is the Susan B. Anthony Birthplace Museum . This museum is dedicated to a woman who played a pivotal role in the suffragette movement. There’s a beautiful collection of postcards commemorating the suffrage, abolition, and temperance movements.

In nearby Natural Bridge State Park, you can view the only natural white marble arch in North America. It was carved as a result of glacial melt over 13,000 years ago. A bridge spans Hudson Brook and twists through a 60 foot gorge.

You can also hike the Cascade Trail . The 1.2 mile trail follows Notch Brook up to a cascading waterfall (photo above). It’s an easy one hour or so trail, with one riverbank crossing.

• Where to stay in North Adams : Porches Inn, Topia Inn, Tourists
• Where to eat in North Adams : Gramercy Bistro, Grazie, Public Eat and Drink

7. Williamstown

Just next door to North Adams is the college town of Williamstown, home to Williams College. Williams College is one of the “Little Ivies,” known for its ivy covered buildings, Gothic chapel, and beautiful architecture. It’s one of the best places to visit in the Berkshires.

Williamstown is also home to the Clark Art Institute , a must visit in the Berkshires. It’s one of the United State’s best museums, focusing on historic European and American art.

The amazing museum has been fully renovated and expanded in a mix of architectural styles.

The museum is home to some beautiful works by John Singer Sargent and Winslow Homer and a world class collection of French Impressionist paintings (30 Renoir paintings!)

The Clark Institute is located on a 140 acre compound. It has well marked (and free) hiking trails for year round exploration.

The well manicured paths wind through woods, cresting at the top of Stone Hill. From there, you’ll have a beautiful panoramic views of Williamstown and Vermont’s Green Mountains.

At the Williams College Museum of Art you’ll find modern and contemporary art to admire.

If you’re visiting in the summer months, you can attend the Williamstown Theatre Festival, a 2002 Tony award winner for outstanding regional theater. Williams College offers concerts, recitals, and theatrical productions.

If you didn’t hike at the Clark Institute, try Pine Cobble Trail. The 3.2 mile trail is a steadily ascending climb to the 1,894 foot summit. From the top, you’ll have beautiful views of Williamstown and North Adams.

• Where to stay in Williamstown : Orchards Hotel, River Bend Farm, House at Sweet Brook Farm
• Where to eat in Williamstown : A Frame Bakery, Coyote Flaco, Mezze Bistro & Bar, ‘6 House Pub

8. Mt. Greylock State Reservation

Head back to Notch Road and continue your descent from Williamstown. The road leads to Mt. Greylock State Reservation , one of the best places to visit in the Berkshires.

Its centerpiece is a 3,491 foot peak. You can drive up to the summit for Massachusetts’ highest viewing point, which features views of 5 states on a good day.

There are plenty of marked hiking trails at Mt. Greylock as well, many starting from the parking lot at the mountain’s base. The trails range from easy to aggressive. Click here for the online trail map.

At the top, there’s a War Tower Memorial for WWII veterans, a panoramic view, and Bascom Lodge where you can eat lunch.

dmission to Mount Greylock State Reservation is free. But you’ll have to pay for parking.

• Where to stay in Mt. Greylock : Bascom Lodge
• Where to eat near Mt. Greylock : Bascom Lodge, Eat on North, Powder Hounds Restaurant

9. Lanesborough | Lakeview Orchard | Cheshire

Then descend back down, exit the park, and take Route 7. Turn left on Summer Street and pull into the small town of Lanesborough, where you’ll see pastures and horse farms.

A slight detour off Summer Street takes you to Lakeview Orchard . There, you can pick your own bushel of apples and sip on apple cider. You can also buy pies or grab a sandwich here. The orchard is renowned for its apple cider donuts.

If you have kids, stop in at Whitney’s Farm Market in Cheshire. In the fall, there’s a corn maze, pumpkin picking, and hayrides. The farm also has a large market with baked goods and a deli.

If you want to some adventure, head to Ramblewild . It’s one of the largest tree to tree aerial adventure parks in the northeast US. You can zipline, climb, and swing through 11 acres of forest.

• Where to stay in Lanesborough : There are better lodging options in Williamstown. Otherwise, try the Harbor House Inn in Cheshire.
• Where to eat in Lanesborough : Old Forge Restaurant

10. Berkshire Festivals

The Berkshires usually have a a packed festival calendar. They celebrate gifted artisans, agricultural harvests, and food | music | art. Here are some of the most popular festivals in the summer and fall seasons:

Tanglewood Music Festival — the 200 acre summer home of the Boston Symphony Orchestra, hosting concerts by world famous musicians in its 200 acre spread

Jacob’s Pillow Dance Festival — showcasing world renowned performers of ballet, modern, and international dance

Shakespeare & Company — the annual repertory season is held in the evenings at The Mount

FreshGrass Festival — a bluegrass festival held at MoCA in North Adams

Berkshires Botanical Garden Harvest Festival — one of the most popular fall festivals in Stockbridge celebrating the harvest and crafts

Lenox Apple Squeeze — street festival celebrating the apple harvest in Lenox

I hope you’ve enjoyed my guide to the best places to visit in the Berkshires. If you’d like to take other US road trips or need some US destination inspiration, I have other guides you may enjoy:

• 10 day Road Trip in New Hampshire
• 10 Day Road Trip for Coastal Maine
• Fall Foliage Road Trip in New England
• 25 Prettiest Towns in New England
• 1 Week Road Trip in Vermont
• 3 Day Itinerary for Boston
• Best Day Trips From Boston
• 10-14 Day Itinerary for Southwest US
• 10 Day Southern California Itinerary

If you’d like to visit the Berkshires in Massachusetts, pin it for later.

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Last Updated on March 27, 2023 by Leslie Livingston

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6 Easygoing Towns in the Berkshires You Need to Visit This Year

Last Updated: December 26, 2023 //  by  Ashley Smith Leave a Comment

Living in Massachusetts I hear about the small towns in the Berkshires a good amount. Whether it’s for hiking in the summer or for skiing in the winter, someone I know is always heading to the Berkshires.

So, what all is there to do in the Berkshires and where should you stay? Read on to learn the best stuff these towns in the Berkshires have to offer.

Where to stay in the Berkshires

You could stay at a different hotel for each of these small towns in the Berkshires. However, since many of the most popular things to do in the Berkshires are just a short drive from one another, I’d recommend parking it somewhere central and exploring from there.

There are many great places to stay in the Berkshires , but the most popular towns to base yourself are Stockbridge, Lenox, or Great Barrington. Here are some of the best hotels in each of these:

Red Lion Inn – Stockbridge, MA

The Red Lion Inn is your quintessential Berkshires hotel—historic, antique-y, friendly. This historic landmark opened as a small tavern back in 1773 and has since grown into one of the most popular hotels in the Berkshires.

Many of the most popular things to do in the Berkshires are just a short walk or short drive away. While here, eat at one of their three restaurants and bars, check out their library and garden, and swim in their outdoor pool.

People love the old décor and the comfort of the place, as well as its location for sightseeing. Check them out here: Red Lion Inn

Yankee Inn – Lenox, MA

If the aesthetic you’re going for is “a little bit less like my grandmother’s house,” then the Yankee Inn is for you.

While many of the Berkshires hotels fancy that antique, lace curtain style, the Yankee Inn is more of a modern lodging situation. (With just a touch of lace, I guess they can’t help it.)

The Yankee Inn has a Superb guest rating, both an indoor and outdoor pool, 24-hour fitness center, 24-hour business center, and a bar/lounge. They offer free WiFi and free parking, as well as an incredibly friendly staff. Check them out here: Yankee Inn

Fairfield Inn & Suites – Great Barrington, MA

And if it’s absolutely no lace, no antiques, no four poster beds you’re looking for, the Fairfield Inn & Suites in Great Barrington is where you need to stay.

Though it lacks that characteristic Berkshires charm, the Fairfield Inn & Suites has everything you’re accustomed to: large indoor pool, simple rooms, a fitness center, a business center, and a 24-hour front desk.

They offer free WiFi, free parking, and even a free full breakfast. It’s your standard chain hotel but, with a Superb rating from reviewers, you’re sure to be pleased with your stay. Check them out here: Fairfield Inn & Suites

6 easygoing towns in the Berkshires

Now that you’ve chosen your base, it’s time choose which of these towns in the Berkshires you’re going to visit and what there is to do there.

1. Stockbridge, MA

Stockbridge, Massachusetts is one of the more well-known towns in the Berkshires and home to many of the area’s most popular sights and activities.

It’s primarily known for being the home of American painter Norman Rockwell and to walk down Stockbridge’s Main Street is to, quite literally, walk through a painting.

Stockbridge is said to be one of the quintessential American small towns and, if you’re coming from Boston (2 hours) or New York City (3 hours), this town will surely be a welcome sight.

Also check out: The Only Boston Bucket List You Need : 65+ Best Uniquely Boston Experiences (w/ Pro Tips!)

What to do in Stockbridge

Stockbridge is one of the many towns in the Berkshires big on history and art. Here are some of the best things to do in Stockbridge:

• Norman Rockwell Museum – home to the world’s largest collection of original Normal Rockwell paintings
• Naumkeag – Public garden, historic home, 48-acre “architectural masterpiece”
• Berkshires Botanical Gardens – 24-acre botanical garden featuring over 3,000 plant species
• Enjoy a meal at the Red Lion – The hotel mentioned above serves some delicious meals in some cool historic spaces.

2. Lenox, MA

Lenox, Massachusetts is mostly a summer destination as it’s the summer home of the Boston Symphony Orchestra (which I’ll get to in a second). And like many of the small towns in the Berkshires, Lenox couldn’t be cuter. Lenox is dotted with massive privately-owned mansions, historic libraries, and natural beauty.

What to do in Lenox

Lenox is home to one of the Northeast’s most popular festivals, among other things.

• Tanglewood Music Festival – The summer home of the Boston Symphony Orchestra hosts a variety of musical guests and performances.
• The Mount – historic mansion home of American author Edith Wharton ( The Age of Innocence )
• Ventfort Hall – historic mansion and Gilded Age Museum
• Pleasant Valley Wildlife Sanctuary – Over 1,100 acres of forests, wetlands, and meadows; 7 miles of hiking trails; ponds and wildlife viewing

3. Great Barrington, MA

On its list of Best Small Towns in America, Smithsonian Magazine listed Great Barrington, Massachusetts as number one. On this list of easygoing towns in the Berkshires I have listed it as #3, purely by coincidence.

Besides that accolade, Great Barrington is known for a couple other points: being the birthplace of author and civil rights activist W.E.B. Du Bois, and for its plethora of antique shops.

It’s also popular for its dining scene. This small town in the Berkshires has over 70 restaurants—far more than a town this size should have. Apparently antiquing makes ya hungry.

What to do in Great Barrington

If antiquing isn’t why you came to town, rest assured there is more to this town than old furniture and knick-knacks.

• Monument Mountain hike – One of the most popular hikes in the Berkshires, said to be the inspiration for Herman Melville’s Moby Dick .
• Bash Bish Falls – 80-foot waterfall on the Massachusetts/New York border you can reach by hard trail or by easy trail.

Also check out: Visit Boston on a Budget : 13+ Ways to Save Money on Your Next Trip

4. Pittsfield, MA

Pittsfield, Massachusetts is known as the heart of the Berkshires and is the largest of all the towns in the Berkshires. (Population 47,000) It’s been featured on best places to retire lists and is even called the “Brooklyn of the Berkshires.” Clearly, it’s not as simple as many of the smaller towns in the Berkshires.

What to do in Pittsfield

Being the cultural center of the Berkshires that it is, you’re going to find a number of festivals, food and drink experiences, shopping, and many other ways to spend your days. Such as:

• Herman Melville’s Arrowhead – the former home of Moby Dick author Herman Melville
• Berkshire Museum – containing collections on fine art, natural sciences, ancient artifacts, and more
• Pittsfield State Forest – featuring 30 miles of trails for hiking, mountain biking, horseback riding, and more
• Hancock Shaker Village – former Shaker commune, now a living history museum

5. Chatham, NY

You read that right, not all towns in the Berkshires lie in Massachusetts. The Berkshires are actually located at the junction of Massachusetts and New York, down to Connecticut and up to Vermont.

And unlike the picturesque little towns of Massachusetts, Chatham, NY is something else entirely. More on the “pastural” side of things, this eclectic little town is a lot greener and a little more remote.

What to do in Chatham, NY

But like all the other towns in the Berkshires, Chatham is full of historic buildings and plenty of art and shopping experiences. Check out:

• Ooms Conservation Area at Sutherland Pond – Miles of trails, beautiful mountain views, birdwatching opportunities, and a variety of other outdoor activities
• Chatham Brewing – local microbrewery offering tons of beer and food
• Hudson Chatham Winery – Get your hand-made batches of wine, cheeses, and desserts here with beautiful Hudson Valley views.
• Check out some historical architecture – like the Crandell Theater and Union Station

6. North Adams / Adams, MA

Listed as the smallest city in Massachusetts, North Adams is easily one of the quaintest towns in the Berkshires. Adams and North Adams are just 10 minutes apart, and just 15 minutes from both the New York and Vermont borders.

What to do in Adams and North Adams

Though they may be small, they are home to some of the most popular things to do in the Berkshires. Like:

• Mount Greylock – popular hiking spot and the highest point in Massachusetts, also part of the Appalachian Trail
• Massachusetts Museum of Contemporary Art – For something quite different than many of the art museums in the Berkshires
• Natural Bridge State Park – home to the only natural white marble arch in North America (made from 550 million-year-old marble)

More info for your trip to the Berkshires

• Where to stay: Read reviews and find great places to stay here .
• Car rentals: Check out the best area rental car deals here.
• Pick up this New England guidebook before you go!
• Want more New England? Check out these posts .

Like this post? Have questions? Let me know in the comments! Enjoy your time in the Berkshires!

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About Ashley Smith

Ashley is a historian and Oktoberfest expert & tour guide. She has traveled to 33 countries and specializes in quick trips throughout Europe and the Americas that prioritize hiking adventures, museums of all kinds, cultural experiences, and jam-packed itineraries. She hails from Memphis, TN and currently lives in Boston with her husband and two feline sidekicks.

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The Berkshires   Travel Guide

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15 Best Things To Do in The Berkshires

Updated May. 11, 2022

The Berkshires region of western Massachusetts is known for its outdoor adventures like hiking and water sports, as well as cultural experiences. Home to several performance centers, including Tanglewood and Jacob's Pillow , the Berkshires offers

• All Things To Do

Tanglewood Tanglewood

The summer home of the Boston Symphony Orchestra, this open-air music venue attracts thousands of visitors who come to enjoy a variety of classical, contemporary, jazz and pop music performances every year. The Boston Symphony Orchestra has spent its summers at this grand estate located between the towns of Lenox and Stockbridge since 1937. Over this time, many renowned artists have also made appearances at the venue, including Yo-Yo Ma, Earth, Wind & Fire and Steely Dan. Tanglewood is most popular during the summer when the weather allows for sitting on the property's large lawn during performances. Still, the grounds also house multiple indoor facilities and restaurants, which enable visitors to enjoy programs, galas, events and cocerts year-round.

Reviewers call Tanglewood a "music lover's paradise," with charming scenery that keeps travelers returning year after year. Visitors appreciated the well-manicured grounds and world-class concerts, but recommend bringing your own lawn chairs, food and drinks to avoid the hefty prices of concession trucks, restaurants and stores on the property. Whether you bring your seating or rent from the facility, friendly staff can help you get situated, according to reviewers.

Jacob's Pillow Jacob's Pillow

Follow the sounds of dancing feet to the Berkshires' 225-acre National Historic Landmark, Jacob's Pillow. A recipient of the National Medal of Arts, Jacob's Pillow is home to one of the most renowned dance training centers in the nation as well as the longest-running international dance festival. The festival, which takes place from mid-June to the end of August, hosts more than 50 dance companies and 500 free performances, talks and events.

Audiences love watching performances with the backdrop of the picturesque Berkshires. Reviewers appreciate the pre-show talks that explain the upcoming performances' background and meaning. What's more, visitors are permitted to bring their own picnics and wine to avoid the expensive prices at the on-site restaurants. However, visitors who indulged in a meal at the property's Old Inn On The Green say it is worthwhile.

Monument Mountain Monument Mountain free

Follow in the footsteps of literary legends Herman Melville, Nathaniel Hawthorne and Oliver Wendell Holmes with a hike up Monument Mountain. Calling the town of Great Barrington home, Monument Mountain brims with history and striking views that overlook the Housatonic River Valley and Mount Greylock . Come prepared with your walking shoes and water – it takes some endurance to tackle the 720-foot elevation gain on the way up to Monument Mountain's 1,642-foot Squaw Peak.

Outdoor enthusiasts who visit the Berkshires will appreciate the mountain's various trails, which range in difficulty. If you're looking for a leisurely climb up, take the Indian Monument Trail – a 1 1/2-mile path that climbs the west face of the mountain. For the most direct route, take the Hickory Trail, which measures less than a mile, but is considered the most strenuous. As you make your ascent, heed the advice of recent visitors and take in these views with a mid-hike picnic.

Mount Greylock Mount Greylock

Mount Greylock boasts the highest point in the state of Massachusetts. Located in the town of Adams, its summit reaches 3,491 feet. On a clear day, visitors to the summit can see as far as 90 miles. The area offers a variety of seasonal activities, including hiking, camping, hunting, snowmobiling, skiing and educational programs led by local park rangers.

Recent travelers said Mount Greylock is a great excursion because it caters to hikers of all levels thanks to a variety of trails. Helpful and friendly recommendations by the rangers at the visitor center were also appreciated and added to the quality of hikers' experiences. Reviewers agree that the views are worthwhile, whether you're taking the scenic driving route or tackling one of the many hiking trails. At the peak, travelers appreciated the touching Veterans War Memorial Tower and a meal at the Bascom Lodge . Past visitors recommend making a reservation to avoid waiting once arriving at Mount Greylock's summit for a sunset dinner.

Clark Art Institute Clark Art Institute

The Sterling and Francine Clark Art Institute in Williamstown displays exhibits featuring collections of European and American paintings, sculptures, drawings, photographs and other unique forms of art ranging from the Renaissance to the early 20th century. You can observe masterpieces throughout the museum on your own or download a multimedia guide to your smartphone (for an extra fee) to virtually walk you through exhibitions. Outside the museum, you'll find picnic tables and nature trails.

Recent visitors expressed excitement about the wide range of world-class displays within the museum. They also suggested picnicking by the reflecting pool followed by a scenic stroll on the campus trails outside the Clark. Reviewers also appreciated that the museum offers something for everyone thanks to its diverse and ever-changing exhibits.

The Mount The Mount

Once the home of author and humanitarian Edith Wharton, this Lenox estate includes a 42-room country house and formal gardens that span nearly 50 acres. Wharton's home and gardens teem with stories of her vibrant life, philanthropic work and literary legacy. House and garden tours offer visitors a glimpse into the author's past, while the seasonal "Backstairs" tour provides a behind-the-scenes look at the servants who lived at The Mount. Ghost tours are also available from July to October. Visitors at The Mount will also find a terrace cafe, a bookstore, forest hiking trails and a cultural center, which plays host to a variety of community events.

Visitors applaud the entertaining and informative guides, who they say bring Wharton to life. Reviewers suggest setting aside several hours to tour the property and gardens, as you'll want to take your time admiring the estate.  

Pleasant Valley Wildlife Sanctuary Pleasant Valley Wildlife Sanctuary

Located in the town of Lenox, this 1,211-acre wildlife sanctuary run by the Massachusetts Audubon Society features 7 miles of trails, a large pond, and striking views of forest, meadows, wetlands and wildlife. There are many well-marked walking trails to explore, which range in length and difficulty. The All Persons Trail fits its title as a mostly flat and 30- to 40-minute easy loop around Pike's Pond where hikers can often spot beavers. For the more adventurous, the Trail of the Ledges is a 3-mile loop that challenges visitors to hike a steep vertical to the top of Lenox Mountain, which reaches an elevation of 2,126 feet. The strenuous hike up is well worth the vistas of Mount Greylock , the Taconic Range and the Catskill Mountains. What's more, Pleasant Valley offers many different programs for people of all ages and abilities, including birding, canoeing, paddling and more.

Visitors say there are so many hiking loops to choose from that it would simply be impossible to do them all in one day. Luckily, the staff in the nature center can help groups decide which trails would suit them best and where they might find beavers along the way.

Jiminy Peak Mountain Resort Jiminy Peak Mountain Resort

This four-season resort in the town of Hancock is constantly bustling with visitors eager to try its many activities. The largest ski and snowboard resort in southern New England, Jiminy Peak offers a variety of winter sports, including snowshoeing, and lessons for all ages and levels. As the snow melts away, Jiminy Peak transitions into a summer mountain adventure park. Among the attractions are an alpine slide, a scenic chairlift ride, a rock climbing wall and the self-guided Aerial Adventure Park, which features six elevated courses. Plus, several hiking trails offer views of Mount Greylock and the Jericho Valley. Families with children enjoy spending time at this resort together. Recent travelers applauded the wide range of activities for children and adults and the reasonable prices.

The resort is open year-round, but hours for each activity and facility can vary. Prices for the adventure park and ski lift also vary based on age, time and activities. For information on pricing, visit the Jiminy Peak website .

Herman Melville's Arrowhead Museum Herman Melville's Arrowhead Museum free

Restored by the Berkshire County Historical Society, the home of "Moby-Dick; or, The Whale" author Herman Melville is open to visitors interested in learning more about the literary legend. Located in the historic town of Pittsfield, the house was inhabited by Melville from 1850 to 1863. Along with the home, visitors can tour the barn and surrounding grounds, which feature a farm and nature trail.

Even some of Melville's biggest fans said they were surprised at the amount of new information they learned during their tours. Recent visitors appreciated the interesting stories shared by the site's knowledgeable tour guides, as well as the gift shop, which sells a variety of books about and written by Melville.

Ramblewild Adventure Park Ramblewild Adventure Park

The Berkshires offers plenty of hiking opportunities to get your bearings on the ground, but Ramblewild Adventure Park enables visitors to experience the Massachusetts mountains from an entirely different altitude. This treetop adventure course challenges outdoor adventurers and beginners alike as they climb and weave through the obstacles in the hemlock groves of Feronia Forest. Ropes, ladders, bridges, swings and zip lines are among the 130 elements across the eight different routes that await visitors 45 feet above the forest floor. Along with its aerial park, Ramblewild also offers hiking trails and snowshoeing.

Previous travelers visiting Ramblewild as a family say the aerial course is among the best things to do in the Berkshires. Reviewers credit the encouraging staff and breathtaking views as prime reasons to plan a trip. Visitors also appreciate the range of courses for all skill levels. Reviewers say the 3 1/2-hour timeslot enables visitors to try out a handful of courses and take in the landscape from different parts of the forest, all while getting a great workout.

Massachusetts Museum of Contemporary Art Massachusetts Museum of Contemporary Art

The Massachusetts Museum of Contemporary Art (MASS MoCA) in the town of North Adams features impressive visual and performing arts from both well-known and emerging artists. The diverse artwork including everything from sculptures to virtual reality to painting to photography. What's more, the museum hosts more than 75 performances year-round, ranging from contemporary dance to outdoor silent films with live music. Whether you're looking to see art or make art, the MASS MoCA is sure to fuel your creative mind.

Travelers say this industrial museum is a work of art in itself. This unique space offers so much eclectic artwork that reviewers report wandering its halls for hours. Visitors are especially impressed with the thought-provoking contemporary artwork and how each exhibit is strikingly different from the last, making for a memorable experience.

Norman Rockwell Museum Norman Rockwell Museum

The Norman Rockwell Museum walks visitors through the life and prolific works of the well-known American artist. Located in Stockbridge – the town Rockwell called home for the last 25 years of his life – the museum features a variety of exhibits displaying the artist's work, as well as his studio. In the museum cottage and surrounding grounds, festivals, workshops, speakers and galleries take place regularly.

Reviewers recommend tagging along on a tour, in which knowledgeable guides give thoughtful insight into the painter and his artwork. Recent visitors also suggested strolling the attractive grounds and having a picnic instead of eating the meals offered on-site. Stockbridge is home to many fresh and locally-sourced restaurants; the famed Red Lion Inn is just down the street.

Naumkeag Naumkeag

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Hancock Shaker Village Hancock Shaker Village

Berkshire Botanical Garden Berkshire Botanical Garden

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Places to visit in Berkshire

Visit Berkshire for castle estates set in oak-lined deer parks and picturesque country downs with grazing horses. There's something regal about Berkshire. Dress to impress with top hat and tails on royal race days. You'll see the training yards and gallops in the Berkshire Downs and Lamborne on your country rambles. Drop into bustling Reading for sporting fixes from football to rowing and half marathons. Pack wellies and tents for rock festival season. The chalk ridgeways, meandering rivers and downs make for great walks. Get your bearings of this south eastern county from the summit of Walbury Hill, a former Iron Age camp. Top places to visit in Berkshire include Windsor Castle, the UK Wolf Conservation Trust, Highclere Castle and the scrumptious Fudge Kitchen.

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24 hours in Windsor

A sprawling royal town with elegant landmarks and riverside pubs, Windsor is so much more than just Legoland.

Uncover Cliveden's unique past

Discover a country house in Berkshire with a chequered past.

Location: Maidenhead, Berkshire

See the changing of the Guards at Windsor

If there’s one essential experience in Windsor, it’s taking in the spectacle of the Changing of the Guard. This tradition brings history and the public together.

Location: Windsor, Berkshire

June events: Enjoy a flutter on the horses at Royal Ascot

Enjoy a quintessentially British day out at Royal Ascot – a highlight of the summer social calendar and one of the most exciting events of the year.

Location: Ascot, Berkshire

See London in miniature at the LEGOLAND® Windsor Resort

See the London Eye, Big Ben and Tower Bridge made entirely of LEGO in the LEGOLAND Windsor Resort's Miniland attraction.

See flowers in bloom at The Savill Garden

Enliven your senses with a walk around one of Britain's finest ornamental gardens.

Investigate The Most Noble Order of the Garter in Windsor

The Knights of the Garter, the most senior and oldest British order of Chivalry, has its colourful and historical base at St George’s Chapel, Windsor.

Head to Royal Windsor for a truly memorable heritage break

Discover a rich mix of history, culture, heritage and fun on a short break in Royal Windsor.

Location: The Royal Borough of Windsor & Maidenhead, Berkshire

Enjoy Afternoon Tea with a twist in Windsor

Indulge in the quintessentially English tradition of afternoon tea from a wooden river boat, or whilst dressed in your best vintage clobber this spring.

UK breaks: 24 hours in Windsor

Windsor is more than just Legoland – it’s a sprawling royal town studded with elegant landmarks, riverside pubs and lots of things to see and do.

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Nearby counties to visit.

Oxfordshire

Visit Oxfordshire for skylines pierced with spires and domes, rambling deer parks, gourmet retreats in manor houses, designer outlets and covered markets.

Looking for things to do in Surrey? Visit high octane theme parks, meadow-covered hilltops, Palladian mansions and Henry VIII palaces in this historic county.

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33 beautiful places to visit in Berkshire, England

Most visitors to England come to Berkshire to visit the Queen’s Royal residence Windsor Castle and although Berkshire is considered a Royal County it would be a shame to miss some of the best things to see in Berkshire because it is a county full of history, incredible landscapes, and stunning architecture.

The county town is Reading which is ideally located to explore the Great West Way, the Chilterns , Silchester Roman City walls , the Thames Path or nearby Windsor , Henley or Oxford.

Historically, the English county of Berkshire has been bordered to the north by the ancient boundary of the River Thames. However, much of the border with Oxfordshire in the western part of the county was moved in 1974. This does lead to some confusion when exploring Berkshire as several sites that were in Berkshire are now considered to be in Oxfordshire.

Pros and Cons of Living in the UK

History of Berkshire England

Where is berkshire, england, berkshire travel & transport, things to do in berkshire, windsor castle, windsor great park, swan upping, frogmore house, the savill garden, the berkshire downs, north wessex downs, the ridgeway, basildon park, bisham abbey and manor house, buscot park, didcot railway centre, highclere castle, greenham common, legoland windsor, maidenhead heritage centre, berkshire museum of aviation – woodley airfield, roman silchester, reading museum, reading abbey ruins, the living rainforest, donnington castle, cliveden estate, newbury racecourse, newbury race course, wellington country park, kennet horse boat company, sandhurst military academy.

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The county is one of the oldest in England. It is believed that it dates back to 848 when King Cenwalh granted “three thousand hides by Ashdown” to Cuthred his kinsman. The county is first mentioned by name in 860 and the name was probably originally Bearroc which means hilly and was related to a large forest that used to take up most of the County. Berkshire was alternately claimed by the Anglo-Saxon kingdoms of Mercia and Wessex and it was in Wantage which is now in Oxfordshire that Alfred the Great was born in 848.

With the Norman Conquest of 1066 , the Thames River Valley became a strategically valuable site and William the Conqueror built the first Windsor Castle on the River Thames. The castle has been home to British royalty for over 1000 years.

During the middle ages, Abingdon and Wallingford were in Berkshire and they were the leading towns of the area. Berkshire England is also home to Eton College, England’s best-known boys’ school, endowed by Henry VI and dates in part from the 15th century.

Berkshire borders six other counties: Hampshire directly to the south; Surrey to the southeast; Wiltshire to the southwest ; Oxfordshire and Buckinghamshire, which lie to the north, across the Thames; and Gloucestershire.

How to get to Berkshire

If you drive from Heathrow Airport to Berkshire it will take you around 45 minutes. It’s not a bad drive although around the airport can be quite scary but no worse than Toronto Airport or any other major airport around the world.

If you don’t have a car, the easiest – and cheapest – way to get to or from Heathrow is by bus or coach. Reading Buses runs a service from Bracknell and Slough to Heathrow. The 703 bus travels from Bracknell to Terminal 5 via Heatherwood Hospital in Ascot, Winkfield, Legoland, Windsor and Langley. Buses to the airport run from 4.40 am to 9.05 pm, every day of the week.

Trains in Berkshire serve a number of routes across the county and to other areas. There are several mainline rail routes offering local and regional services. Reading Station has services between Reading and London Paddington station with a journey time of 30 minutes. There are also services to Bristol, Bath, Cardiff Bournemouth and Oxford. Manchester, London and Liverpool.

There are so many amazing things to do in Berkshire, and it is well worth getting out of London and visiting. From historic sites to cultural events, fine English manor houses, ancient Neolithic monuments to gorgeous villages Berkshire has it all. You’ll also find a wide range of family activities and perfect days out for kids. There’s Legoland, Wellington Country Park, Beale Wildlife Park, Go Ape Bracknell a forest adventure and loads of adventures and activities on Bray Lake.

Berkshire is filled with beautiful villages that make for an enjoyable holiday, whether you’re looking for something with high-end offerings or something more quaint and charming. You can find an ideal village destination for your holiday when you search along the banks of the River Thames, which is home to numerous English villages and market towns.

Thanks to the county’s boundaries being changed in 1974 many of the sites and monuments that were originally in the Royal County of Berkshire are now in different counties. For example, Highclere Castle aka Downton Abbey was in Berkshire but now is in Hampshire. Even the British can’t keep it straight.

Places of interest in Berkshire, England

Windsor Castle is the oldest and largest inhabited castle in the entire world and has been around for over 1000 years. Founded by William the Conqueror in the 11th century, it has since been the home of 39 monarchs. This was Her Majesty Queen Elizabeth’s favourite place to spend time and if she wasn’t in Buckingham Palace or Scotland she was here. You know when the royal family is in residence as the flag will be flown from the towers.

Windsor Great Park is a beautiful green space of over 4,800 acres. This is where the Kings and Queens of England used to hunt, fish and ride their horses. There is a herd of red Deer, loads of walking paths, gardens, a lake and a bridleway.

Although the centrepiece of Windsor is the great Windsor Castle there is actually a lot more to see and things to do in Windsor than you realize and it’s a charming small town nestled beside the Thames River in Berkshire.

Just outside the castle stands the iconic statue of Queen Victoria looking over the Royal Town. Wander down to the River where you can take a cruise down the Thames and pass by Ascot, and Eton College. Feed the swans and learn all about the royal swans of Windsor.

The ancient tradition of ‘Swan Upping’ is carried out each year on the river, under the Shadow of Windsor Castle. The tradition dates back to the 12th-c when the crown claimed ownership of all the swans in the country.

In medieval times swans were served at royal banquets and feasts and often were the centrepiece of royal dinners. Fortunately, swans are no longer eaten by royalty and these days Swan Upping is an annual census that consists of rounding up the swans to collect data and assessing the health of the birds. The Swans have their own protector on the Thames (Queen’s Swan Marker), who is responsible for their protection and conservation.

You have probably heard of Frogmore as it was the contentious home of Harry and Meghan before they moved out of England.

Frogmore Cottage is located in Windsor Great Park about a mile from the castle and can be visited by tourists. Queen Charlotte purchased the house in the 1800s and the house was a favourite of Queen Victoria her mother lived there for over 20 years.

You can see Queen Charlotte’s passion for botany reflected in both the house and the gardens where flower paintings by Mary Moser decorate one of the rooms. The Cross Gallery was painted with garlands by Princess Elizabeth, the daughter of George III and Queen Charlotte.

Queen Victoria often visited Frogmore during her long widowhood and worked on her papers there. You can also see watercolours by her daughters, Princess Victoria and Louise in the house.

The historic plantings, including tulip trees and redwoods, provide a rich setting for the garden’s seasonal variations. An 18th-century summerhouse in the form of a Gothic ruin is covered in wisteria in the summer, and a teahouse made for Queen Victoria are both still standing.

The Savill Garden sits in the heart of Windsor Great Park and it is one of the great ornamental gardens of England, designed by Sir Eric Savill, who was commissioned by King George V and his Queen Mary. Within the garden, you can visit the Queen Elizabeth II Temperate House, the Golden Jubilee Garden, and the Rose Garden opened by Queen Elizabeth II in July 2010. The Savill Garden covers 35 acres and contains distinctive interlocking gardens including the Hidden Gardens, Spring Wood, the Summer Gardens, the New Zealand Garden, Summer Wood, The Glades, Autumn Wood and the Winter Beds.

One of Britain’s most well-known racecourses, Ascot holds a special week of races in June each year called Royal Ascot, attended by The Queen, who has had an interest in horses since childhood.

Ascot Racecourse was founded by Queen Anne in 1711 and has since received the patronage of a further eleven monarchs. The Ascot summer race meeting officially became a Royal week in 1911.

A Down is a grass-covered hill and in southern England, they are mainly composed of chalk. The name comes from the Old English dūn which means hill. The main areas of chalk downs lie in Berkshire, Wiltshire, and northern Hampshire. Chalk hills of a similar type are called Wolds in Lincolnshire and in Yorkshire.

Prehistoric sites in the Berkshire Downs include Wayland’s Smithy (Neolithic), numerous tumuli (Neolithic or Bronze Age), the Uffington White Horse which is actually considered to be in Oxfordshire now.

The Berkshire Downs contained many prehistoric settlements that were linked by ancient ridgeways which led from Wiltshire along the chalk ridge of the Berkshire Downs to the River Thames at the Goring Gap, part of the Icknield Way. Settlements uncovered in the river valleys and eastern Berkshire also date from the Iron Age. Roman ruins have been found at Silchester, southwest of Reading, which became a Roman crossroads.

This is an Area of Outstanding Natural Beauty (AONB) and is a designated protected landscape. It straddles the boundaries of Berkshire, Hampshire, Oxfordshire and Wiltshire and covers an area of 668 square miles (1,730 square kilometres). Within the area of the Downs, you will find historic homes such as Highclere and Ashdown House along with natural sights such as the Avebury stones, Wayland’s Smithy, the Uffington White Horse and Silbury Hill to mention a few.

The Berkshire Chalk Downs form part of The Ridgeway National Trail follows the ancient Ridgeway from Overton Hill, near Avebury, and its stone circle to Streatley then follows footpaths and parts of the ancient Icknield Way through the Chiltern Hills in Berkshire to Ivinghoe Beacon in Buckinghamshire. This National Trail is 87 miles (140 km) long.

Another charming English Village Pangbourne is on the Roman road from Silchester to Dorchester-on-Thames and signs of Roman occupation have been uncovered on Shooters’ Hill.

Pangbourne means Paega’s People’s Stream, which indicates that an early Anglo-Saxon chieftain of that name first lived here. The place is first recorded in a grant of land there to Bertwulf, the King of Mercia (the Midlands) in AD 844. This relaxing little village is the perfect place to stop for lunch, perhaps fish in the Thames or shop till you drop in one of its lively boutiques.

This 18th-century Bath-stone house run by the National Trust was inspired by Italian Palladian architecture. It was restored by Lord and Lady Iliffe in the 1950s, who acquired a collection of fine furnishings and carefully selected Old Masters. Basildon Park has been used in several films and TV shows including Bridgerton and Downton Abbey the house was used as the Grantham’s home in London for Rose’s coming out ball.

The gardens today, include a rose garden , and a formal Italianate terrace, built of large stone blocks, which enclose a formal lower lawn and give wide-ranging views over the Thames Valley hills.

Part of the Royal Borough of Windsor and Maidenhead Bisham Abbey is a Grade I listed manor house and its name is taken from the now-lost monastery which once stood alongside. This original Bisham Abbey was previously named Bisham Priory and was the traditional resting place of many Earls of Salisbury.

Bisham Manor House pronounced bizzam is currently run as a Centre of Sporting Excellence and a Conference Centre. The manor house was built around 1260 as a community house for two Knights Templar. In 1310 the building was used as a place of confinement for Queen Elizabeth of the Scots, wife of King Robert the Bruce, who had been captured on Rathlin Island of the coast of Northern Ireland during the Scottish Wars of Succession.

Henry VIII granted the manor house to Anne of Cleves as part of her divorce settlement from him, and it was later bought by the Hoby family, who lived there until 1768. Elizabeth I was a regular visitor at the time of the Hoby family.

The pretty town of Eton is located on the other side of the bank of the River Thames from Windsor and they’re connected by a bridge.

Standing on the pedestrian bridge offers beautiful views of the castle’s water edge, and a walk down will lead you to the world-famous Eton College.

Also, spending time exploring the small village of Eton with its relaxing atmosphere with its art galleries, bookshops, antique shops, and a small museum take a moment to enjoy a quintessentially British dessert Eton Mess during an afternoon tea break.

Buscot Park is a late 18th-century house, set in enchanting landscaped grounds. Extensive pleasure gardens surround the late eighteenth-century house with a Four Seasons garden, water gardens and an Italianate terrace combined with English parklands. The grounds roll down to the Thames plain and incorporate the Little Lake. Buscot Park is one of those locations that was in historic Berkshire but is now in Oxfordshire. You can visit the House & Grounds for £12.00.

Another former Berkshire historic town now considered Oxfordshire . Didcot Railway is a living history museum and heaven on earth for train fanatics with over 21 acres of fascinating railway yards, steam train displays, carriages, wagons and locomotives.

Highclere Castle is more of a “country house” than a castle and is built in Jacobethan style of Bath stone combined with several towers built in an Italianate style, it was completed in 1842, with a stunning park designed by Capability Brown.

Highclere Castle is just one of the filming locations used for the fabulous Downton Abbey Series and films visiting Downton Abbey is easy and makes for a wonderful trip from Windsor. These days Highclere is located in Hampshire and not Berkshire its original location.

You may have heard of the Greenham Common Women’s Peace Camp at the RAF Greenham base which began in 1981. The USA had located Cruise Missiles at the base and it became the focus of the anti-nuclear protests.

After realising that marches and protests alone were not going to get the missiles removed they began to stay at Greenham and blockade the base. Over 250 women joined the protest in 1982 during which 34 women were arrested and one killed. The Camp closed in 2000 and the site was turned into a Commemorative and Historic site.

There are seven standing stones encircling the “Flame” sculpture representing a campfire. Next to this, there is a stone and steel spiral sculpture, engraved with the words “You can’t kill the Spirit”. There is also a memorial plaque for activist Helen Wyn Thomas, who was killed near the site.

Nowadays there are free-roaming cows, horses and ground-nesting birds in place of aircraft, and beautiful lakes, greenery and wooded areas to enjoy along the myriad of footpaths spanning both commons. It’s a dream for walkers, runners, cyclists, dog walkers, wildlife fanatics, and history lovers, and if you’re lucky enough to catch the sunrise on a good day, you’ll be transported to another world entirely.

Greenham Common, particularly its redundant nuclear missile bunkers, is also famous as a filming location, having most notably provided a backdrop for Star Wars: Episode VII – The Force Awakens in 2015.

Sonning is a quintessentially British Village where you will find several celebrities have set up home. From George and Amal Clooney to ex-Prime Minister Theresa May and Jimmy Page and even Boris Johnson lived here.

Although you can’t see Jimmy Page’s garden or house it is called Deanery Gardens. It is an Edwin Lutyens-designed house with a Gertrude Jekyll garden, well hidden by high walls apart from a good view from the top of the church tower and very private.

There has been a mill at Sonning for many centuries. The Domesday Book of 1086 mentions three mills at ‘Sonninges and Berrochescire’. The mill closed in 1969 and remained empty until 1977. The Richards purchased the Mill and they decided to convert it into a live theatre venue.

Check out the historic Bull Inn which dates back to the 16th century it is immediately next to the church away from the river and is owned by the church. The Bull Inn, is the perfect place to enjoy a pint and a Sunday roast dinner.

The French Horn is another great place to stay and dine in Sonning and it has provided hospitality for two hundred years. Originally, a coaching inn, it sits next to the bridge on the banks of the River Thames, which provides a stunning backdrop and wonderful views from the rooms above.

Legoland is one of England’s most famous theme parks whose attractions consist of a mixture of Lego-themed rides, models, and building workshops targeted at children between three and twelve.

The Maidenhead Heritage Centre is a museum dedicated to regional history dating back to the Roman era. The Museum emphasizes World War I and World War II, offering high-definition photos and in-depth narrations of the men and women who fought in past century wars.

One of the most popular exhibits is a Spitfire simulator, where you can get into the cockpit of a replica Spitfire and see what it was like to dogfight and manoeuvre.

It was at Woodley that the legendary Battle of Britain fighter pilot, Douglas Bader,  lost his legs in a flying accident in 1931. Bader was 21 at the time and was attempting some acrobatics, the crash was a result of the wing hitting the ground and causing the plane to roll.

The Museum’s main focus is on the Miles Aircraft, which from 1932 until the late 40s was called Reading Aerodrome. Many of the projects worked on by MLA were for the Ministry of Defense and were classified as top secret. These included black boxes, ejector seats, pressurized helmets, a flying jeep and a remote-controlled flying surveillance unit, called the Sprite.

Silchester was first dug up by the Victorians. The staff and students from Reading University have, over the years, found many incredible items including the first olive stone ever found in the UK, proving that the people were eating these delicacies long before the Romans arrived.

They discovered little bones with marks on them that indicated puppy fur was taken to make fur cloaks, there were ritual burials of cats, dogs and ravens at the site.

In the 19th century the site, Roman Calleva Atrebatum, produced magnificent finds now on display at Reading Museum, including superb mosaics and one of the most famous Roman finds in Britain, a gilt bronze eagle which inspired the novel The Eagle of the Ninth, and the film The Eagle.”

Reading Museum holds almost 500,000 historic objects from archaeology, art, natural history, social history, and world cultures. Including the Roman finds at Silchester and a fabulous copy of the Bayeux Tapestry.

In medieval times, Reading was the site of a great royal Abbey that was one of the largest monasteries in Europe. In 1121, King Henry I announced that he wanted to have a new abbey built at Reading.

King Henry, I died before the Abbey was finished and was buried here in 1136 in front of the high altar. The building work continued and the Abbey Church was officially opened by the Archbishop of Canterbury, Thomas Becket, in 1164. The ceremony was attended by King Henry II (grandson of Henry I) and his retinue.

The Abbey was the fourth largest church in Britain. It was such a large and ornate construction that the building continued for almost 200 years after the original foundation in 1121.

In 1539 Henry VIII had the abbey slighted during his Dissolution and ordered all its valuables and riches sent to him. The Abbey was converted and Abbot’s lodgings were converted into royal accommodation. Out of Henry VIII’s children, Elizabeth I was the most frequent visitor to Reading. Edward VI and Mary with her husband Prince Philip of Spain visited the palace only once.

The Living Rainforest is an indoor greenhouse tropical rainforest located in Hampstead Norreys in Berkshire, England. It is an ecological centre, educational centre and visitor attraction consisting of three glasshouses, operated and run by the Trust for Sustainable Living.

Experience the sheer beauty of this unique conservation project in 2 different rainforest climates under 20,000 sq ft of glass. A stunning collection of dramatic and rare plant species and creatures of the rainforest that thrive in tropical temperatures.

The imposing 14th-century gatehouse of Donnington Castle stands on the crest of a high hill overlooking the Lambourn Valley, across the river from the market town of Newbury. The castle was built in 1386 by Sir Richard Abberbury to control a major road junction and river crossing.

The most famous owner of Donnington was Thomas Chaucer, son of the poet Geoffrey Chaucer, who held the castle in the early 15th century. Ownership later passed to the crown, and several monarchs are known to have stayed here, including Henry VIII (1539) and his daughter Elizabeth I (1568).

Cliveden sits on the border of Berkshire and Hampshire and it is an English Manor House dating back over 350 years. These days it is a hotel and you can tour the gardens and grounds and see the ancient stone clocktower.

Cliveden has often been used for entertainment and for filmmaking. In 1965 the Beatles filmed part of ‘Help’ the movie at the house and famously held races on the Parterre between themselves and the film crew in-between scenes.

Newbury Racecourse was founded in the 18th century and hosts races all year round. A championship racecourse for over 100 years the races include chase and hurdles, and flats.

Wellington Country Park is a country park in Riseley, near Reading. The park consists of 350 acres of coniferous and deciduous woodlands with attractions, several nature trails, and a lake. Perfect for kids up to 8 years old the park contains an Animal Farm, Arthur, a Miniature Railway a splash zone, mini jeeps to drive a dinosaur zone and many more fun activities for kids.

Another beautiful town on the bank of the Thames River. It’s a sleepy 16rh century village whose only landmark is the ancient flint church, but Bray holds two of Britain’s 3-star Michelin restaurants and is a picturesque way to enjoy some fine dining and walk the lanes full of flower-filled gardens.

A really cool way to cruise the River Thames. The Kennet Horse Boat Company has all kinds of river cruises that are horse-drawn. You can cruise the Thames or the Kennet and Avon Canal. Enjoy a romantic cruise , a dinner cruise or simply a cruise to see the sites.

Berkshire has several ancient and important military institutions, including the Royal Military Academy at Sandhurst. The Royal Military Academy organizes historical tours every year where you can immerse yourself in the history of the place. Military training has taken place here for over 200 years since 1812 and you can visit rooms where Winston Churchill, HRH Prince of Wales, King Charles and King Abdullah II of Jordan have trained to become officers.

Berkshire is a beautiful county in England that offers a wide range of activities and attractions for visitors. From exploring the historic Windsor Castle to take a stroll along the River Thames, there is something for everyone here. Whether you are looking for outdoor adventures or cultural experiences, you will find plenty of options in this charming region. So, if you’re planning a trip to England anytime soon, be sure to add Berkshire to your itinerary – it’s definitely worth a visit.

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Faith was born in Ireland raised in Canada and has lived in over 10 countries in Europe including England, Ireland, Scotland, France, Spain, Northern Ireland, Wales, along with Mexico, Antigua, the US and has slow travelled to over 40 countries around the world. Graduating with a degree in Anthropology and Women's Studies Faith is a student of history, culture, community and food and has written about these topics for over 40 years.

• 33 Best Things to Do in the Berkshires

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What are the best things to do in the Berkshires? This part of Western Massachusetts is so special — not just beautiful, but idyllic, like a painting; not just interesting, but one of the most fascinating regions in the state.

Most people come to Massachusetts to visit Boston, or Cape Cod, or Martha’s Vineyard or Nantucket. But there are treasures waiting for you if you’re willing to head out west.

Despite growing up in Massachusetts, I’ve barely seen the Berkshires — I went to summer camp in East Otis for a few years, but that’s it. And I know it’s human nature not to visit what’s right in front of you. You always assume you’ll be able to do that someday, so why do it now?

But in 2021, a time when people have been looking to closer, local getaways, I decided it was time to visit the Berkshires — not only to have fun, but to research extensively, and eventually create guides like this one to help you plan your own trips to the Berkshires.

Did my trip go well? OH, IT DID! I had the best time in the Berkshires — and I can’t wait to show you all the best things to do here.

I would like to acknowledge and honor the Mohican, Wabanaki and Pocumtuc people, the Indigenous stewards and traditional owners of the unceded land now known as the Berkshires.

This post was last updated in June 2021.

Table of Contents

Why Travel to the Berkshires?

The Berkshires are famous for lots of things — Tanglewood, the summer concert series in Lenox . Canyon Ranch, the fancy spa. Art museums and dance and live theater, all set on a mountainous landscape, evergreen forests crisscrossed with country roads.

But the Berkshires aren’t just for rich people doing fancy things. They’re for everyone. There’s lots to see and do in the Berkshires, including lots of low-key activities — and you’re only a few hours from either New York or Boston.

Where the Berkshires excel, in my opinion, is being both an outdoor destination and an arts destination. You can end up fitting a lot of variety into a short getaway.

I know a lot of couples where one person is into the arts and the other is more into the great outdoors. Often, planning a trip for these kinds of couples means someone is always compromising. But some destinations blend culture and nature seamlessly! Like Asheville, North Carolina , or Oaxaca, Mexico , the Berkshires are perfect for travelers who want to mix the outdoors and the indoors on their trip.

Most people drive to the Berkshires, and you need a car to explore the area sufficiently. If you’re flying in, the Albany airport is about 45 minutes away.

Head outside! A lot of outdoor sites like Bash Bish Falls for free; the Berkshire Botanical Garden is free on Tuesdays; get the best $1 cider donuts of your life at Hilltop Orchards, explore the towns, check out cool coffeeshops like Six Depot Roastery.

If you’re looking to attend concerts, shows and events, aim for summer . Fall is gorgeous but very busy; late spring is another good choice.

The three best museums in the Berkshires are the Norman Rockwell Museum in Stockbridge, the Clark Institute in Williamstown, and MASS MoCA in North Adams.

Where are the Berkshires?

The Berkshires are located in Western Massachusetts. Berkshire County is the westernmost county in Massachusetts; anything within Berkshire County is considered “the Berkshires.”

It feels like the Berkshires are comprised of a southern part and a northern part. In the southern portion, popular towns to base in include Stockbridge , Lenox , and Great Barrington. This is the classic small town Berkshires area that most people have heard of.

The northern portion includes towns like North Adams, Williamstown, and Pittsfield. It’s a different feel up here — more urban, not quite as photogenic — but still very much worth visiting.

Even so, the Berkshires are small enough that you can base in one part and explore the whole region. The drive from Great Barrington in the far south to North Adams in the far north, for example, takes just over an hour.

Even so, culturally speaking, people from the north don’t always go south and vice versa. One local told me people from Pittsfield see going to Stockbridge as something you do for a special occasion — even though it’s less than 30 minutes away.

On my trip, I wanted to get to know all of the Berkshires in depth — so I split my time between two bases, Stockbridge in the south and North Adams in the north. More on where I stayed below.

Read More: The Best Towns in the Berkshires

Berkshires Map

The map above is a complete guide to the Berkshires, including everything mentioned in this post, color-coded based on the type of destination. Hope it helps you get the lay of the land.

Best Things to Do in the Berkshires

Some of my friends go to the Berkshires to get away from busy city life. They rent a cabin on a lake, read books, hit up the farmers’ markets, and grill.

That’s a nice way to spend a weekend — but the Berkshires are SO much more than a quiet place to unwind. There is an insane number of things to do in the Berkshires!

I’ve broken it down into four categories: arts and culture, outdoor activities, historic sites, and food and drink.

Arts and Culture in the Berkshires

Don’t even think of planning a trip to the Berkshires without taking in the arts and culture! Whether you’re looking for museums or performing arts, there is so much to enjoy here. Though if you’re here for performances, you should try to time your trip for the summer months.

Norman Rockwell Museum

Norman Rockwell is famous for his scenes of small-town New England, and many of those scenes come from the town of Stockbridge, where he made his home. The Norman Rockwell Museum is a comprehensive collection of his art, from the 300+ Saturday Evening Post covers to his personal items, larger works of art, and works by other artists inspired by him.

I love deep dives into a single artist, watching their work evolve over time. What I especially loved about this museum is how they showed Rockwell’s journey to activism, including the work that went into his portrait of Ruby Bridges, The Problem We All Live With .

Admission to the Norman Rockwell Museum is $20 for adults, $18 for seniors and veterans, and free for active military and children under 18.

If you know anything about the Berkshires, you’ve probably heard of Tanglewood ! This venue in Lenox is the summer home of the Boston Symphony Orchestra, and performances are in a theater that opens to the great outdoors, letting people enjoy outstanding music under the stars.

Each summer, you can experience the Boston Symphony Orchestra, the Boston Pops, the Tanglewood Music Center, and more. (One of the most popular events is John Williams night, which some of my friends go to see every year!)

See the full schedule of Tanglewood performances here.

Clark Institute

Did you know that the Berkshires are home to one of the best collections of Impressionism in the world? I had no idea! The Clark Institute in Williamstown is a museum featuring American and European art from the Renaissance through the early 20th century.

Most impressive, though, is their massive collection of Renoir paintings. I felt as if I were in Paris. What a special find this place is.

There are rotating exhibits throughout the year, and be sure to leave enough time to explore the trails outside, many of which lead to even more sculptures.

Admission to the Clark Institute is $20 and free for students with ID and children under 18. The outdoor walking trails are free to all.

Shakespeare and Company

If you’re in the mood for some classic theater, Shakespeare and Company performs the Bard’s shows in Lenox all summer long, and other plays throughout the year. In addition to the performances, Shakespeare and Company does some of the best theatrical training in the region.

See the full schedule of Shakespeare and Company performances here.

Mass MoCA — the Massachusetts Museum of Contemporary Art — is one of the most imaginative and stunning museums in Massachusetts, as well as an inspiring story of reinvigorating the former mill town of North Adams. The ever-changing exhibits here are intended to cover every medium and break conventional boundaries.

The museum is in the former Sprague Electric Company, now an expansive building filled with light from every angle. Plan to spend a lot of time here, because the campus has everything from an ice cream shop to a craft brewery! Plus, you never know which works of art will end up captivating you.

Modern art isn’t for everyone — but I bet you’ll enjoy this place, as it’s genuinely one of the best things to do in the Berkshires.

Admission to MASS MoCA is $20 for adults, $18 for seniors and veterans, $12 for students with ID, $8 for age 6-16, and free for children under 6.

Williamstown Theater Festival

If you’re looking for both classic and cutting-edge theatrical performances, be sure to check out what the Williamstown Theater Festival has to offer during the summer months. (Yes, they call themselves WTF!)

This regional Tony award-winning festival features all kinds of shows and events in this little northwest corner of Massachusetts, from educational workshops to late-night cabarets.

See the full schedule of Williamstown Theater Festival performances here.

Berkshire Museum

If you’re looking to explore more of what makes the Berkshires what they are, look no further than the Berkshire Museum in Pittsfield. This museum has sections on the science, ecology, history, and culture of the Berkshires.

Many of the exhibits are more oriented toward kids — like the aquarium and animals in miniature section — but I did love the Feigenbaum Hall of Innovation, which profiles different notable residents of the Berkshires, like W.E.B. DuBois and Susan B. Anthony.

Admission is $13 for adults, $6 for ages 4 to 17, and free for children under 4.

Jacob’s Pillow

You’ve got your music, you’ve got your theater — why not add some dance into the mix? The Berkshires are home to Jacob’s Pillow, a National Historic Site in Becket home to the nation’s longest-running dance festival. Each summer, Jacob’s Pillow hosts more than 50 dance companies for live performances, as well as talks, workshops, and more.

From classic performances to more avant-garde offerings, Jacob’s Pillow is a must during the summer if you’re a dance fan.

See the full schedule of performances here.

Williams College Museum of Art

Set on the idyllic Williams College campus, the Williams College Museum of Art features exhibits by emerging artists from all over the world.

The museum is currently closed due to COVID, but we hope it will open soon. Admission is free.

Outdoor Activities in the Berkshires

You don’t need to be a hardcore athlete to enjoy the outdoors in the Berkshires. If you’d like a simple and easy outdoor activity, head to the Berkshire Botanical Garden. If you’re a hardcore hiker, Mount Greylock is calling your name! And if you’re a novice hiker who would like an easy walk through the woods with a beautiful waterfall, you can’t beat Bash Bish Falls .

Bash Bish Falls

I know, your mind wants it to be “Bish Bash Falls” but it’s actually “Bash Bish Falls”! This is the kind of hike that I love — it’s easy, not too long, and there’s a big payoff at the end. I think it’s one of the best free things to do in the Berkshires.

This waterfall is in Bash Bish Falls State Park in the southwest corner of Massachusetts — but you can actually hike there from either the Massachusetts side or Taconic State Park on the New York side. The hike from the Massachusetts side is shorter (0.6 miles or one hour return) but steeper; the hike from the New York side is longer (1.5 miles or 90 minutes return) but not as steep.

Since I didn’t have my hiking shoes with me, I chose to hike from the New York side — and I loved the novelty factor of walking from one state into another! What a lovely way to spend the morning, having been fortified with a pastry from Berkshire Mountain Bakery.

Keep in mind that you’re not allowed to swim in the falls. But I bet you’ll be satisfied even without a dip in the river.

Admission is free.

Berkshire Botanical Garden

Located right in Stockbridge, the Berkshire Botanical Garden is one of the oldest display gardens in the Northeast US. The garden displays all kinds of interesting plants from all over the region, all landscaped beautifully and designed to teach you more about them.

If you’re looking for a casual stroll while enjoying the beauty of nature, this is a great option. (And if you’re here on a Tuesday, you can take advantage of free admission!) The garden also puts on events like toga and tai chi classes among the flowers, workshops, receptions, and even classes in watercolors and birding.

Admission to the Berkshire Botanical Garden is $15 for adults, $14 for seniors, and free for children under 12. Admission is free to all on Tuesdays.

Berkshire Camino Guided Hikes

If you’re looking for a guided hike with a twist, take a look at Berkshire Camino — a hiking company inspired by the Camino de Santiago, the life-changing pilgrimage across Spain. Owner Mindy Miraglia loved her time on the Camino and today she brings Camino magic to small hiking tours in the Berkshires.

The Camino is all about hiking from one town to the next, and discovering what lays before you. That’s how these hikes are structured — you could start out in Housatonic and hike to Stockbridge, or maybe start in Lee and hike to Lenox. There are shorter walkabout-style hikes within towns, too.

Berkshire Camino has walkabouts from $18 per person, half day hikes from $80 per person or $150 for two people. Multi-day hiking trips are available, too.

Mount Greylock

If you’re looking for a bigger challenge, consider hiking Mount Greylock — the highest point in Massachusetts! Mount Greylock State Reservation, near Adams, is home to more than a dozen hiking trails, ranging from “easy” to “aggressive.” Hiking to the summit of Mount Greylock is one of the most strenuous routes.

Even if you’re not up for a tough hike, you can still enjoy one of the easier hikes while taking in the gorgeous scenery.

Admission to Mount Greylock State Reservation is free; parking is $5 for Massachusetts residents and $20 for those from out of state. See the full hiking guide here.

Ashuwillticook Rail Trail

Don’t you love when old railroad tracks are repurposed into something better? The train tracks here fell into disuse in 1990, so they turned it into a 10-foot-wide paved trail, running from Cheshire to Lanesborough to Adams. Throughout the rail trail you get to enjoy views of the Hoosic River, mountains, and lakes — and if you’re here for the fall foliage, even better!

If you’re bringing your bike to the Berkshires — or even your skateboard or rollerblades — this would be my top recommendation for you. But even if you’re just here to walk or run, it’s a lovely place to enjoy a bit of nature in between all your museum-hopping.

The Ashuwillticook Rail Trail is free and there are several free parking lots along the trail.

Housatonic River Walk

You’ll see the Housatonic River winding throughout the Berkshires, but perhaps its best segment is in Great Barrington, where they’ve created the Housatonic River Walk . Signs direct you between two private homes and suddenly you’re on a beautiful path along the river.

There are two segments of the River Walk — you can see them on a map here — and there are displays at the entrances that tell you more about what you’re seeing.

Great Barrington is probably the best town in the Berkshires to spend an afternoon exploring the shops and downtown. But nothing delighted me more than the River Walk!

The Housatonic River Walk is free.

Pontoosuc Lake

I was driving through Pittsfield and admiring a lake in the distance — then I saw a parking lot leading to lakeside picnic tables. I had to stop and visit! Pontoosuc Lake is divided between Pittsfield and Lanesborough, and it’s a lovely place for a quick stop.

This lake is more popular for boating and fishing than swimming, and boat rentals are available. If you’re spending time in the Pittsfield area, you may want to check out the Pittsfield National Forest as well.

Pontoosuc Lake is free.

Monument Mountain

One of the more stunning hikes in the Berkshires is up Monument Mountain in Great Barrington. There are three trails leading to the summit, all under three miles. In addition to stunning views of the rocky mountain and expansive landscape, you might see hawks or bald eagles!

Fun fact: authors Herman Melville and Nathaniel Hawthorne met while sheltering from a storm while hiking Monument Mountain — and became friends for life. Melville even dedicated Moby-Dick to Hawthorne. (You are constantly reminded of this in the Berkshires!)

Admission to Monument Mountain is free; parking is $6.

Natural Bridge State Park

North Adams might be known as the funky art town, but they also have one of the nicer state parks in the region: Natural Bridge State Park. This park is home to the only natural white marble arch in North America — which was formed 550 million years ago!

If you’re a geology fan, this is the park to visit. It’s remarkable seeing how the water carves around the stones. You can hike through a white marble quarry — also the only one in North America.

Admission to Natural Bridge State Park is free. Parking is $5 for Massachusetts residents and $20 for those from out of state.

Pleasant Valley Wildlife Sanctuary

One of the hidden gems of the Berkshires is the Pleasant Valley Wildlife Sanctuary — 1,000 acres of forest, meadows, wetlands, and mountain slopes, right on the edge of Lenox. Run by the Audubon Society, this is home to some of the best wildlife watching in the region, from beavers to birds.

Some of the highlights are a challenging hike to the summit of Lenox Mountain; an All Persons Trail, a universally accessible trail with Braille, audio, and tactile descriptions; and an active beaver colony that can be viewed from Pike’s pond.

Admission to Pleasant Valley Wildlife Sanctuary is $5 for adults, $3 for seniors, and $2 for children age 2-12.

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort is a great spot for mountain fun in the Berkshires. This family-friendly park has everything from Alpine slides to mountain coasters, a giant swing, chairlift rides, a rock climbing wall, a bungee trampoline, and more.

Coming in the winter? They have plenty of skiing.

For those over 54 inches, summer admission to Jiminy Peak is $59 for six hours and $39 for four hours. For those who are 38-53 inches, summer admission is $49 for six hours and $29 for four hours. Buy online ahead of time because there is a $5 per ticket surcharge if you wait to buy at the door.

Skiing in the Berkshires

If you’re up for a winter visit, the Berkshires have a lot of places to ski. In addition to Jiminy Peak Mountain Resort , check out Ski Butternut , Otis Ridge , Bousquet Mountain , and Berkshire East .

Historic Sites in the Berkshires

For centuries, the Berkshires have been a draw for artists, writers, and creatives of all types. It didn’t hurt that it made a peaceful retreat that wasn’t too far from both New York and Boston!

Fed up with the snobbery of Newport, Rhode Island, literary legend Edith Wharton decided to move to the Berkshires in 1901. Her home in Lenox was christened The Mount , she spent many of her most prolific writing years here, and today it’s one of the most stunning historic homes in the region.

Wharton had a lot of style — and I found myself longing for her furnishings! She actually had a pale pink dining room with fuchsia and gold cutlery! The house is a remarkable portrait of how the wealthy lived during this time period, and it makes you think about how idyllic surroundings can inspire you as an artist.

Admission to the Mount is $20 for adults, $18 for seniors, $13 for students with ID, and free for children under 18. The grounds are free.

Ventfort Hall

Also in Lenox, Ventfort Hall is an imposing mansion built in 1893 for Sarah Morgan, sister of J.P. Morgan. Today it’s a fully furnished home that doubles as the Museum of the Gilded Age. It’s designed in a sumptuous manner teaching you how people lived in this interesting point in time.

I found the guides here to be excellent, passionate and well-versed in the history and architectural quirks of this property. Good guides definitely make you more excited about a place!

Most people will tell you that The Mount is the best historic home in the Berkshires — but I had so much affection for Ventfort Hall.

Admission to Ventfort Hall is $18 for adults, $17 for seniors, $10 for students age 18-23 with ID, and $7 for age 5-17, and free for children under 5.

Red Lion Inn

Everyone in the Berkshires knows all about the Red Lion Inn in Stockbridge — even casual Berkshires visitors are well versed in it. The Red Lion Inn was first established as a tavern in 1773, and though it’s gone through various iterations since then, that makes it one of the oldest continuously operated inns in the United States.

It’s a piece of living history, and it’s an interesting place to walk through and enjoy the decor of centuries past.

I stayed at the Red Lion Inn for part of my trip ( more on that below ), but you don’t have to be a hotel guest here to enjoy it. Enjoy a glass of wine at the Lion’s Den pub, eat at the restaurant (one of the few places in Stockbridge open on a Tuesday, I learned!), or simply stake out one of the rocking chairs on the front porch.

Chesterwood

You may not know artist Daniel Chester French off the top of your head, but you definitely know his work — he created the Lincoln Memorial. Today, his legacy lives on at Chesterwood , his home in Stockbridge, where you can visit his studio and learn more about his life and work.

French considered the Berkshires his personal heaven and spent the six warmer months of the year living here, enjoying views of the mountains and creating smooth, sumptuous sculptures. I highly recommend taking the guided tour so you can learn more about his life and work.

Honestly, much of his life was similar to artists today — like when he did a job for free because they promised him paid work in the future — and then they gave him nothing. His friend Ralph Waldo Emerson bullied them into paying him!

Admission to Chesterwood is $20 for adults, $18 for seniors, $15 for active military or veterans, $10 for young adults age 13-21, and free for children under 13.

The most difficult thing about Naumkeag may be pronouncing it (hint: it’s nom-keg , and it helps to picture an animal nomming on a keg of beer). This historic shingle-style home has 44 rooms and was home to generations of the Choate family. While the inside is interesting to explore, the gardens are the big draw here.

You can enjoy sumptuous flower gardens, quintessential Berkshires views over the countryside, and even a Chinese-style garden. I recommend pausing to get a beverage while sitting in Adirondack chairs looking over the landscape.

Admission to Naumkeag is $10 for adults, $15 for seniors and students with ID, $5 for children 3-12, and free for children under 3.

Hancock Shaker Village

The Shakers were a fascinating sect within American society, and their legacy lives on at the Hancock Shaker Village in Pittsfield, a historic center and working farm. The Shakers believed in communal life, celibacy, confession of sin, racial and gender equality, simplicity, and pacifism.

In this village, you can see the homes that were divided into the men’s area and the women’s area (and yes, the celibacy is why they died out!), and you can learn about how they lived self-sufficiently on this farm, growing food, raising animals, and producing crafts. It’s an interesting look into a group that gets little attention outside history classes.

Admission is $20 for adults; $18 for seniors, AAA members, MTA cardholders, and active and retired US military; $8 for youth age 13-17; and free for children under 13.

When you picture the home of Herman Melville, what do you imagine? Somewhere set on a cliff overlooking a stormy sea? You’re probably not picturing a yellow house with a red barn in the Berkshires, overlooking Mount Greylock in the distance! Melville moved to Pittsfield in 1850 to write in solitude; he lived at Arrowhead for 13 years. While here he wrote some of his best works, including Moby-Dick .

To see the house itself, you go on a guided tour and learn all about Melville’s history and his life in the Berkshires. If you’re a Moby-Dick fan, this is a place you should prioritize.

Admission to Arrowhead is $16 for adults, $14 for seniors, $10 for students, and free for children under 13.

Food and Drink in the Berkshires

You might not think of the Berkshires as a culinary destination — but wait until you see what this place has to offer! Some of my favorite experiences in the Berkshires involved the fabulous local cuisine.

Be sure to double-check the opening hours, because many places are closed Monday through Wednesday.

Farm to Table Dining in the Berkshires

One nice thing about visiting the Berkshires is that so many restaurants serve farm-to-table cuisine. Here are some notable ones worth visiting:

The Prairie Whale in Great Barrington , a funky and welcoming restaurant in the Brooklyn of the Berkshires, serves products from their farm in nearby Monterey. Don’t be afraid to try the pig head rillette.

Mezze Cafe + Bar in Williamstown originally served Mediterranean small plates — but has since grown to offer dishes of all sizes with New England ingredients.

The Old Inn on the Green in New Marlborough is a bit of the beaten path but well worth the stop — especially for the Sunday-Wednesday-Thursday prix fixe menu, with three locally sourced courses for just $46.

John Andrews Restaurant in South Egremont , located in an 18th century farmhouse, has been doing farm-to-table menus since 1990. They serve original dishes from artisan producers and grow quite a bit in their garden.

cafeADAM in Great Barrington not only makes use of local producers and dishes — they also feature locally foraged ingredients, like mushrooms from Chef Adam’s secret spot.

The Old Mill in South Egremont features New England ingredients interpreted into new and exciting dishes — and has a commitment to using only wild or organically farmed seafood.

Berkshire Mountain Bakery

If you’re looking for some excellent baked goods, I recommend stopping at Berkshire Mountain Bakery in the tiny town of Housantonic. (It also makes a great stop on the way to Bash Bish Falls, I found out!) This small bakery specializes in sourdough and high-end bakeries, and people from all over the region drop by to pick up loaves of bread.

I grabbed a Kouign-Amann (because I’m fancy — or, really, because I watch the Great British Bake-Off) and it was everything that pastry should be: soft but strong, flaky, covered with sugar.

There is a second location in Pittsfield that doubles as a pizza cafe! And if you really miss the bread, they deliver within the US.

Six Depot Roastery and Cafe

Some coffeeshops are worth going out of your way — and Six Depot Roastery and Cafe in West Stockbridge is well worth the visit. This cafe takes coffee and tea SO seriously. They only serve coffee from sources around the world they’ve evaluated to be of the highest standards.

This is a wonderful cafe to visit for breakfast or brunch. There’s plenty of indoor and outdoor seating. They serve an assortment of bakery treats and light meals. I enjoyed a fantastic coffee and a Spanish tortilla. And the town of West Stockbridge is adorable.

While Six Depot is my favorite coffeeshop in the Berkshires, there are plenty more you can visit! (I tried to visit THEM ALL! And got to almost all of them!) My second-favorite is Tunnel City Coffee , which pairs well with a visit to the Clark Institute. (There are a few locations but I recommend their flagship in Williamstown, which is huge, has a giant case full of gorgeous pastries, and has a jovial student crowd.)

Some other places with excellent coffee are Stockbridge Coffee and Tea in Stockbridge, Shots Cafe in Lenox, and Fuel in Great Barrington.

Hilltop Orchards

You might see Hilltop Orchards in Richmond on your Berkshires map — and come here for the apple picking. Or for tasting the local artisanal cider from Jmash Cidery. And let’s not forget the local wine tasting from Furnace Book Winery. There are even hiking trails with great mountain views.

But one item stands out here. CIDER DONUTS.

Holy hell, these cider donuts may be the best cider donuts I HAVE EVER HAD IN MY LIFE. They’re on the small side, almost unfathomably moist, and covered with delicious cinnamon sugar.

I ordered two and somehow ended up with three in my bag. IT WAS NOT ENOUGH. I should have gotten six for $5!

Trust me…if for no other reason, you need to come here for the cider donuts. This is probably one of my top three things to do in the Berkshires. There’s a reason why everyone recommends them!

Bright Ideas Brewing

One of the cool things about MASS MoCA in North Adams is the ecosystem that grew around it — cool new hotels, restaurants, coffeeshops, and bars. And I enjoyed spending an evening at Bright Ideas Brewing !

This brewery features a rotating selection of delicious home-brewed beers — some made with international ingredients. I particularly enjoyed the Northern Lights, made with an unexpected ingredient — taiheke from New Zealand!

I also appreciated that the brewery was around the corner from my hotel, Porches at MASS MoCA, so I could happily imbibe without worrying about driving.

Other craft breweries worth visiting in the Berkshires are Berkshire Brewing Company in South Deerfield, Shire Breu-Hous in Dalton, Big Elm Brewing in Sheffield, and Barrington Brewery and Restaurant in Great Barrington.

Where to Stay in the Berkshires

If you’re looking to stay in the Berkshires, you should decide whether you want to concentrate on the south (Stockbridge, Lenox, Lee, Great Barrington) or north (North Adams, Williamstown, Pittsfield). Technically you can do it all in one trip, as I did.

I chose to try out two nights in the south at the Red Lion Inn in Stockbridge and one night in the north at Porches at MASS MoCA in North Adams. These are two small, independent hotels, the kinds of places I love to stay. Both hotels hosted me on a comped media stay.

As soon as I told my friends I was visiting the Berkshires, several of them told me, “Oh, are you going to the Red Lion?” If anywhere is THE place to stay in the Berkshires, it’s here.

The Red Lion Inn is one of the oldest continuously operating inns in the United States, having been open since 1773. Today, the inn has expanded and covers several buildings within a few blocks — including Maple Glen, the building where I stayed.

The Red Lion is located in downtown Stockbridge, which I think is one of the best places to base in the Berkshires. Not only is it a beautiful town with lots to see and do, it gives you easy access to Lenox, Great Barrington, and nearby small towns; plus, if you want to do Williamsburg and North Adams for the day, this part of the state is less than an hour away.

This was my queen room with a fun mix of colors and patterns.

Lots of seating and a good area for working, if you need to.

I loved the display sculptures in Maple Glen!

My room blended country charm with modern amenities. I appreciated the large size — and that it came with a decent-sized bathtub! The wifi worked well — very important, as Stockbridge is a dead zone for phone signal — and it was nice and quiet at night.

I went to the restaurant one night, which serves classic Yankee cuisine. The restaurant, the pub, and even the front porch feel like a gathering place in Stockbridge, with interesting people passing through.

One tip: don’t bring all your bags when you check in. I did, then I found out I had to schlep them outside and down the street to another building.

Rooms from $148 per night.

Porches at MASS MoCA

North Adams is all about reinvention, and Porches at MASS MoCA is one of the coolest building concepts I’ve seen. The hotel is built from a long strip of 19th century Victorian row houses along the Hoosic River, reconstructed and joined into one long building.

Porches calls itself “whimsical” frequently — and they love the phrase “granny chic.” Personally, I loved it! Such a cool mix of vintage and modern accessories, a vibrant color palette, homey and comforting. It fits North Adams perfectly.

I loved the colors, those lamps, and the divider between rooms.

This is full-on granny chic and I loved it.

This was the inside of one of the Victorian houses — the indoor/outdoor mix kind of reminded me of Vegas, believe it or not.

North Adams makes a good base for visiting the northern part of the Berkshires — towns like Williamstown, Lanesborough, Pittsfield, Florida, and Cheshire. And Porches is right across the street from MASS MoCA — which meant I could enjoy two beers at Bright Ideas Brewing without having to drive!

If you want to hang out at Porches, there are plenty of rocking chairs on the front porches, as well as a pool area in the back.

Rooms from $149 per night.

Overall, these were two great places to stay in the Berkshires, but they were so different! Overall, I loved the location and history of the Red Lion, but I preferred the design and vibe of Porches. If you’re coming to the Berkshires for three nights and don’t mind changing accommodation, why don’t you try both?

See more places to stay in the Berkshires here.

Berkshires Travel Tips

Here are some things you should know before traveling in the Berkshires:

Phone signal is poor in parts of the Berkshires. In fact, the entire town of Stockbridge is a dead zone for phone signal, which shocked me. If you’re using your phone for GPS, as I did, you should load directions while you have access to wifi.

The Berkshires are quiet during the week, especially outside high season. I visited from Monday through Thursday, which I thought would allow me fewer crowds. It sure did — and TONS of places were closed! You should check to make sure your favorite attraction isn’t closed when you’re visiting.

Prices can quickly snowball in the Berkshires. Most museums and historic sites cost around $20. That can quickly add up when you’re doing three or four in a day! It’s best to figure out before you go how much you want to spend and what your biggest priorities are.

Look for combination tickets if you’re hitting up a lot of museums. You can buy a combination ticket to MASS MoCA, the Clark Institute, and the Williams College Museum of Art for $34. Pick it up in any of the three spots.

A lot of coffeeshops in the Berkshires close at 2:00 PM during the week. I found this disappointing, as I love a midafternoon coffeeshop visit when I travel.

Best Time to Visit the Berkshires

Most people say that the best time to visit the Berkshires is either the summer or the fall. The summer because it’s when the most events are on — Tanglewood, Jacob’s Pillow, all the theater performances — and the fall is when you get the best foliage.

Keep in mind that the absolute busiest time in the Berkshires is during summer and fall weekends. You can expect big crowds and high prices with both peaking on the Fourth of July, Labor Day, and Columbus Day.

If you’re looking to experience the best foliage in the Berkshires, time your visit from late September through mid-October. Columbus Day is usually pretty solid for foliage. Though it’s always a smart idea to check an almanac as this can vary from year to year.

I visited the Berkshires in mid-May and it was a surprisingly good time to visit. There were no performances going on, but the weather was absolutely glorious; it was actually much sunnier and warmer than Boston! (That doesn’t always happen, though. May in New England can often be chilly and rainy.)

Winter is a slow and quiet time of year — but this is a great time to visit the Berkshires if you’re looking to ski, snowshoe, or bundle up by the fireplace.

Keep in mind that early spring in New England is “mud season” — and most if not all of April falls into this category. Spring hits later here than many parts of the US.

How to Get to the Berkshires

You need a car in the Berkshires. Can you do the Berkshires without a car? I’m sure someone has, but I really don’t recommend it.

Everything requires driving. Even if you base in a town like Stockbridge, getting to local attractions like the Norman Rockwell Museum, Chesterwood, Naumkeag, and the Berkshire Botanical Gardens requires a 10-minute drive!

Most people drive to the Berkshires. Depending on where you base, it’s about a 2:15-2:45 drive from Boston and a 2:45-3:15 drive from New York City.

If you’re flying to the Berkshires, the closest major airport is in Albany, about a 45-minute drive from Stockbridge.

There are bus and train connections to Pittsfield.

Are the Berkshires worth it?

Yes! Absolutely! I loved my trip to the Berkshires, and my only regret was that I waited so long to visit this wonderful part of my home state.

And to my fellow Bay Staters, New Englanders, and tri-staters — if you haven’t been to the Berkshires yet, maybe it’s time for you to make the trip! Pick a long weekend and start researching. I think you’ll fall in love with this beautiful part of the world.

Western Massachusetts:

• Best Towns in the Berkshires, Massachusetts

Best of Boston:

• What NOT to Do in Boston
• Where to Stay in Boston: Best Neighborhoods & Hotels
• 40+ Fun Things to Do in Boston at Night
• Best Time to Visit Boston
• 24 Interesting Things to Do in Cambridge, Mass.
• 12+ Best Day Trips From Boston
• 21 Best Museums in Boston

Cape Cod & the Islands:

• Which of the Towns of Cape Cod is Best for You?
• 24 Fab Things to Do in Cape Cod
• 22 Fabulous Things to Do in Provincetown, MA
• Which Of The 6 Martha’s Vineyard Towns Is Best For You?
• A Guide to Oak Bluffs, MA — Home of the Gingerbread Houses
• A Guide to Edgartown, MA — Prettiest Martha’s Vineyard Town
• A Guide to Vineyard Haven, MA — Authentic Town on Martha’s Vineyard
• 24 Cool Things to Do in Lenox, MA
• 12 Fun Things to Do in Stockbridge, MA

North Shore:

• 27 Fun Things to Do in Rockport, Mass.
• 25 Spooky, Haunted Things to Do in Salem, Mass.

Thanks to the Red Lion Inn and Porches at MASS MoCA for hosting me for three nights altogether in the Berkshires. I also received comped admission to the Norman Rockwell Museum, Naumkeag, Chesterwood, The Mount, Berkshire Botanical Garden, Ventfort Hall, Hancock Shaker Village, Clark Institute, MASS MoCA, the Berkshire Museum, and Arrowhead. All opinions, as always, are my own.

1 thought on “33 Best Things to Do in the Berkshires”

Hi there, I’ve been to all 50 states and last year for the first time we did the Poconos in PA and loved it. The Berkshires are on my list so glad to read it not’s just for the rich (think real housewives lol) and very excited to see there are waterfalls. I can’t wait to visit this area. Nikki

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Berkshire Villages | The 20 Best Villages In Berkshire, England

Berkshire villages include many of the prettiest places in the south of England.

The county lies between Oxford and London and contains much of the gorgeous countryside around its county town of Reading. In particular, it contains much of the Thames Valley, with many of the villages we’ve chosen below lying on this waterway.

Table of Contents

A beautiful suburban area sitting on the bank of the Thames River. Enjoy fine dining and sightseeing. Grab a bite to eat at one of the Michelin-starred restaurants such as the Fat Duck, voted as the best restaurant in the world by Restaurant magazine. A village that is rich with historical buildings and churches is sure to impress.

Located in West Berkshire, Bucklebury is one of several alluring villages in Berkshire, notable for its rich history and beautiful buildings.

You can visit Bucklebury farm park and enjoy seeing several beautiful breeds of deer, including Red Deer and Fallow. For a rural trip to Berkshire, Bucklebury is the destination to go.

Kintbury is a lush town on the Kennet and Avon Canal. Here you can find yourself canoeing, kayaking, or fishing. The scenery is gorgeous enough to simply take a stroll after lunch or sit out for an outdoor picnic.

There are two pubs located right in the village, as well as tennis and football clubs and an outdoor leisure center. 

Littlewick Green

Full of charming homes and green and lush surroundings, Littlewick Green is home to historic landmarks such as the Redroofs theater.

Located near Maidenhead and set around a village green space, Littlewick Green is no stranger to beautiful countryside views. Home to art and performance, it’s the source of historical musical compositions by Ivor Novello and the filming location for several episodes of the popular British crime drama Midsommer Murders.

A large riverside Berkshire village on the Thames River that is ideal for a vacation near the water. It began historically in 1893 and has a musical past which continues today. Here you can find wildlife mixed with local pubs and shops.

The village has schools as well as a railway station that serves the Great Western Main Line.

If you’re looking for villages in Berkshire known for adventure, then Streatley has opportunities for outdoor enthusiasts. Located on the Thames River, you can find something for everyone. Try your hand at golf at the Goring and Streatley Golf Club, a 6,355 yard golf course, or for cycling enthusiasts can ride up Streatley hill for a peaceful ride with a breathtaking view.

Old Windsor

Old Windsor is one of the more prehistoric Berkshire villages, located between the Thames River and Windsor Great Park in the east and west, respectively.

There are four pubs located in Old Windsor as well as several local shops and restaurants. At the south end you will find the Beaumont Estate, dating back to the year 1300.

Welford is a rural village in West Berkshire located on both sides of the Lambourn River. Home to the Welford Park House, held for centuries by a Benedictine Monastery called Abingdon Abbey.

Welford Park is a visiting attraction notable for its floral displays in the early springtime. A lovely white perennial called Snowdrop blooms at this time.

For a relaxing trip full of historical sites, visit Hurley and witness first hand its rich history. Some buildings date back to more than a thousand years.

For outdoor adventures, you can enjoy kayaking, boating, fishing, or simply spending a quiet time cruising the waterways. You can take bus transport from Maidenhead or the closest train station from Marlow or Henley.

Winkfield Row

Settlement of Winkfield Row officially dates back to the early Medieval era, although it is thought to have been occupied much earlier.

If you want history, you can visit the King George Field Memorial in remembrance of King George V. The parish has a primary school, Winkfield St. Mary’s Church of England Primary School as well as an independent prep school.

Waltham St. Lawrence

Waltham St. Lawrence is located in East Berkshire with a small population of about 1,500. The nearest train station is at Twyford, followed by Maidenhead and Bracknell. A historic village with buildings possibly dating back to the pre-thirteenth century. You’ll find local historical churches as well as a rich history of notable authors and publishers.

Performing arts and theater. Restaurants, concerts, food, and nightlife. Sonning theater is a highlight. Local pub for some food and a pint of beer. Sonning also includes rugby fields as well as hockey fields.

Additionally, you can enjoy sailing and water skiing across the Thames River on the Caversham Lakes.

Notable residents include George Clooney and his wife.

The civil parish village of Lambourn has a rich history and a few disasters, including a breakdown of law and order after the civil war in England and Normandy between 1138 and 1153, resulting in what is known today as The Anarchy. The town is notable for its horse racing enthusiasts and professionals. Additionally, you find a theater, pubs, and a local nature reserve.

For beautiful architecture, you can visit the Medieval Church which is dedicated to the archangel Michael. Since 1974, the area has been designated a conservation site to protect its history. Hayley Green, a notable area of Warfield, borders Hayley Green Wood, a wildlife nature reserve. 

Located on the north-east edge of Berkshire, Cookham is considered to be Britain’s second wealthiest village.

A popular tourist destination filled with art and literature history as well as restaurants and pubs. It’s home to the Stanley Spencer Gallery and many famous historical figures, including artists Isaac Pocock and Frank Sherwin.

Sunningdale

Golf enthusiasts will have a good time in Sunningdale as there are golf courses with peaceful, woodsy scenery. Sunningdale is notable for its mansions, such as Charters, a Grade-2 historic mansion famous for its art deco architecture. Notable residents include Emma Forbes, Billy Ocean, and Richard Beckinsale.

White Waltham

A beautiful and green area clustered in the midwest of Littlefield Green and Paley Street parish.

It’s made up of country houses (such as the one pictured) and is home to organic gardens and farms which are open for the public to visit. With lush and fertile agriculture, White Waltham is a village with no shortage of green space. 

Ufton Nervet

A village located in West Berkshire that sits between the Kennet Valley and the crest of low hills. The village is an archaeological site where scattered artifacts from the Mesolithic era have been uncovered. The village is home to three manors, including Ufton Robert, Ufton Nervet, and Ufton Pole.

Lower Basildon

Lower Basildon is full of shops as well as pub-restaurants such as The Red Lion. If you love nature and parks, then you can stop by the Beale Wildlife Park, which houses small exotic species, birds, and farm animals. You can travel around the village by bus, which runs on Tuesdays.

Chaddleworth

The major areas of Chaddleworth village consist of farmland with scattered woods, including Nine Acre Wood, Down Copse, and Spray Wood.

The village is green with some nice amenities and landmarks, a school, a pub, and even a local microbrewery called The Indigenous Brewery.

This West Berkshire village contains some six miles east of Newbury. It is home to the Wolf Conservation Trust where nine different breeds of wolf reside.

Beenham has one pub and one primary school. Bus routes connect to Calcot and Thatcham.

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Discover the Berkshires

Visit The Berkshires

Discover the hidden gems and vibrant culture of the Berkshires! Whether you’re looking to visit the Berkshires for its renowned performing arts or explore the picturesque landscape dotted with fresh water lakes and rivers, we have curated lists and guides to unveil the best this region has to offer. The Berkshires isn’t just a haven for arts and culture; it’s a gateway to some of the most breathtaking outdoor recreation spots in the Northeast, with a terrain boasting rolling hills and towering peaks. Seeking a dynamic vacation? The Berkshires offers diverse retreat centers, rich visual arts, and a delectable food culture, ensuring a memorable experience regardless of the weather or your mood. Dive in to explore what makes a visit to the Berkshires so unique!

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Explore the towns of the Berkshires

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Historic Berkshire Guide

Ben johnson, facts about berkshire.

Welcome to ‘Royal’ Berkshire, so called because Berkshire is home to Windsor Castle, the largest inhabited castle in the world. Built by William the Conqueror, Windsor Castle has been a royal home and fortress for over 900 years. The monarch stays here every June for Royal Ascot and also to attend the service of the Order of the Garter .

Situated to the west of London, this romantic county boasts some lovely countryside. The River Thames meanders through the north of the county; towns and villages such as Pangbourne and Cookham sit prettily on its banks. For walkers, the ancient Ridgeway passes through Berkshire, and the Berkshire Downs offer many opportunities to explore.

Historic attractions in Berkshire include Shaw House and grand Highclere Castle, TV's Downton Abbey . Newbury is at the heart of England's 'Silicon Valley' and is surrounded by pretty villages such as Sonning, which enjoys a beautiful situation on the River Thames. Sonning is described by the author Jerome K. Jerome in Three Men in a Boat as "the most fairy-like little nook on the whole river".

Legoland is a great attraction for children of all ages. Beale Park near Reading is also a great day out for the family, as is the Tropical Rainforest attraction near Newbury. And adults can enjoy a flutter on the horses all year round at Newbury Racecourse.

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8 Scenic Stops Worth Getting Off The Berkshire Flyer Amtrak To See

• The Berkshire Flyer offers a short yet scenic journey between NYC and Pittsfield, showcasing majestic Berkshires views.
• Tickets start at $32 for coach-class, making it an affordable and convenient travel option for an unforgettable weekend escape.
• With stops in picturesque towns like Yonkers, Poughkeepsie, and Hudson, the Berkshire Flyer promises something for everyone to enjoy.

For rail enthusiasts looking for an unparalleled, unforgettable experience, Amtrak's Berkshire Flyer train is coming back for season 3 on June 21st. It will run this year from June 21 to September 2, 2024, the last day of Labor Day weekend. It takes passengers on a scenic ride between New York and Pittsfield, offering a refreshing weekend escape in the majestic Berkshires. With scenic views of the Hudson River, the Catskills, quaint towns, and the Berkshire Mountains, it is one of the short yet scenic train rides in the USA .

Wondering how long the train is from NYC to the Berkshires? The Berkshire Flyer takes just over four hours between Penn Station’s Moynihan Hall and Pittsfield’s Joseph Scelsi Intermodal Transportation Center . Departing from New York City on Friday afternoon and returning from Pittsfield on Sunday afternoon, this is a perfect weekend escape. This year, the Berkshire Flyer will also run a new Sunday morning service from New York City to Pittsfield.

The question now is: how much does the Berkshire Flyer cost? Well, the Berkshire Flyer is an affordable and convenient way to travel, with coach-class tickets starting at $32 (depending on the time of booking). Tickets are already on sale, so securing a spot on the scenic Berkshire Flyer Amtrak route for summer is easier for travelers!

Moving on, where does the Amtrak Berkshire Flyer stop? The Berkshire Flyer makes six picturesque stops between New York City and Pittsfield: Yonkers, Croton-Harmon, Poughkeepsie, Rhinecliff, Hudson, and Albany-Rensselaer. The final stop, Pittsfield, amid the stunning Berkshires, also offers a plethora of experiences.

From outdoor adventures to cultural delights and a ton of cool summer destinations in the Berkshires , the many scenic Berkshire Flyer stops have something for everyone. Check out the stops along this scenic Amtrak route and get ready to embark on an incredible adventure this summer.

For more information and to book Amtrak Berkshire Flyer tickets, visit Amtrak's official website .

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New york city, new york, the starting point: a vibrant and iconic city with endless attractions and experiences.

There's a plethora of beautiful places to visit in New York City , one of the most popular destinations worldwide. With delicious cuisine, unparalleled cultural activities, shopping, nightlife, entertainment, and much more, NYC promises an unforgettable urban adventure as the starting point of the Berkshire Flyer train.

The Berkshire Flyer starts from Penn Station at 3:15 pm on Fridays. There will be a new service on Sunday mornings at 10:49 am from the same station.

Yonkers, New York

A fantastic waterfront destination with urban charm, scenic beauty, and cultural richness.

Yonkers, the very first stop on the Berkshire Flyer train from New York City, is a great destination with urban charm and natural beauty. It's one of the many safe solo travel destinations in the US with so much to do and see.

The town boasts beautiful parks, a bustling waterfront, and cultural attractions. So, there is never a dull moment! The city is home to numerous museums and galleries, including the Hudson River Museum. Plus, its scenic waterfront provides the ideal setting for farm-to-table dining and leisurely strolls.

Croton-On-Hudson, New York

Discover riverside charm, historic allure, and outdoor adventures near new york city.

The next stop on the Berkshire Flyer is Croton-on-Hudson, a charming riverside village along the Hudson River. It is a great escape from the city's bustle and entices travelers to spend a day in Croton-on-Hudson exploring its scenic beauty, historic charm, and outdoor recreation.

Its picturesque waterfront setting provides opportunities for kayaking and boating, whereas historical landmarks and museums are fun places to discover the area's rich history. Plus, the abundance of outdoor activities, such as hiking, cross-country skiing, and picnicking, fills the trip with fun memories.

Poughkeepsie, New York

A picturesque hudson river city with history, culture, and natural beauty.

The beautiful town of Poughkeepsie , another scenic stop on Amtrak's Berkshire Flyer route, is popular for the iconic Walkway Over the Hudson, the longest elevated pedestrian bridge in the world.

This charming college town has a rich history visible in its iconic landmarks and museums, as well as a vibrant arts and cultural scene. Nestled along the Hudson River, this city offers opportunities to enjoy water activities and delicious cuisine, making it a worthwhile stop on the Berkshire Flyer route for exploration.

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Rhinecliff, new york, a pretty town with riverside charm, historic architecture, and a vibrant arts scene.

The next stop on the Berkshire Flyer is another one of the many beautiful Hudson River towns in New York : Rhinecliff. It is a great place to take a short break from NYC's hectic life and immerse oneself in the surrounding landscape, history, art, and culture.

Visitors can soak in the breathtaking waterfront scenery, learn about the town's rich history through its exquisitely preserved architecture and landmarks, or just simply stroll through the town to find out what this hidden gem is all about.

Hudson, New York

Art galleries, boutiques, history, and local flavors make this town a world apart from nyc.

Nicknamed "the friendly city," Hudson , even though it's only two hours away from NYC, feels a world apart from the city's frantic pace. Nestled in the Hudson Valley, this historic city is a fantastic location to slow down and enjoy a scenic vacation without leaving the state.

The town boasts some of the most wonderful antique shops, restaurants, coffee houses, and hotels in New York. Historical charm is what makes it special, where visitors can immerse themselves in the city's rich architectural heritage, with well-preserved 18th and 19th-century buildings.

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Rensselaer, new york, historical charm, scenic beauty, and proximity to albany.

The last stop on the Berkshire Flyer in New York before heading into Massachusetts is Albany-Rensselaer Station, which serves as the gateway to even more scenic routes and charming history . Situated in Rensselaer, New York, just across the Hudson River from Albany, this Amtrak station astonishes guests with its majestic historical splendor.

The city offers a scenic vacation rich in historical significance. Discover the city's rich history at Crailo State Historic Site, explore its cultural side, and visit the nearby state capital, Albany, which is great for history and outdoor enthusiasts .

Pittsfield, Massachusetts

Quaint, scenic, and culturally rich destination in the berkshires.

Pittsfield, nestled in the western Massachusetts mountains, is a serene retreat brimming with abundant natural beauty, recreational opportunities, and cultural experiences. While downtown has a lively art, music, and food scene, a range of outdoor adventures, such as hiking, boating, and skiing, are just a few minutes away in the gorgeous Berkshire Mountains.

Just over four hours away from NYC by the Berkshire Flyer, Pittsfield is among the New England cities with small-town charm and is a perfect weekend destination. The train returns to NYC from Joseph Scelsi Intermodal Transportation Center on Sunday afternoons at 3:35 pm (however, it will return on Monday afternoon, September 2, over Labor Day weekend).