Touted as one of the best getaways from Boston, the Berkshires is an idyllic vacation destination at any time of the year.
Located in Western Massachusetts, and backed by picturesque rolling hills, farmlands, forests, serene vistas, the region is the perfect place to unwind and refresh your soul.
It also has a rich history of arts, literature, and culture.
Curious about things to do in the Berkshires? Brace yourself for an extraordinary treat!
The Berkshires comprises two cities and several small towns.
The best way to see this region is by basing yourself out of one or two of these towns and driving around to places of interest.
In this guide, we’ve put together a handy list of things to do in the Berkshires, categorized by the most popular towns there.
THINGS TO DO IN BERKSHIRES, MASSACHUSETTS
Where are the Berkshires
Best things to do in the Berkshires
Map – Berkshire Attractions
How to get to the Berkshires
Weather in the Berkshires
Best time to visit the Berkshires
Where to stay in the Berkshires
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Where are the Berkshires
Located in Western Massachusetts, northwest of Connecticut, the Berkshires are a highland region strategically located between New York and Boston.
The Berkshire hills are an extension of the Green Mountains in Vermont.
A map of the Berkshires below indicates the most popular towns and cities in the region.
BEST THINGS TO DO IN THE BERKSHIRES, MASSACHUSETTS
Once a mill town, North Adams is now a hub of culture, arts, and recreation in the Berkshires.
North Adams is one of the smallest cities in the country, surrounded by the highest peak in Massachusetts and with proximity to scenic driving routes, a state forest, and a state park.
It is also home to indie coffee shops, antique stores, boutiques, and one of the best contemporary art museums in the country.
Here are some of the best things to do in North Adams.
Admire the innovative collection of modern art at MASS MoCA
Set in a former factory, The Massachusetts Museum of Contemporary Art (MASS MoCA) is a dynamic museum with well-curated, interactive exhibits that incorporate photography, audio, video, dance, film, and painting, among others.
The museum is spread over three floors, and there are permanent and rotating exhibits on display, featuring works that keep people of all ages engaged.
One of the biggest attractions inside Mass MoCa is the Sol Lewitt collection which comprises a series of 105 large-scale wall drawings by the artist spanning three floors!
They also have a kid’s area, where little ones can participate in fun activities. The museum also hosts regular events and performances.
Mass MoCA is truly a one-of-a-kind place that requires reservations and a fair amount of time on hand to explore! Buy your tickets here.
Visit the noteworthy Clark Art Institute
The Clark Art Institute is located in the town of Williamstown, a fifteen-minute drive away from North Adams.
This beautifully maintained Clark Institute is one of the handful of museums dedicated to art and research.
Inside, you will see art pieces from 16th-19th century painters and sculptors, including works by Renoir, Gaugin, and John Singer Sargent.
In addition, the museum also has hiking trails with outdoor works of art, cow pastures, and a large outdoor space with picnic tables for outdoor meals. It is certainly a hidden gem among museums, with a nice cafe as well.
Admission to the museum is $20 for adults. See admission hours and buy tickets here.
While you’re visiting the Clark Art Institute, make sure to read up on these 11 fabulous things to do in Williamstown MA.
Drive, bike, or hike up to the top of Mt. Greylock
A visit to the summit of Mt. Greylock is an absolute must-do in the Berkshires!
Located on the western side of the town of North Adams, at 3,491 feet, Mt. Greylock is the highest point in the state of Massachusetts.
Drive on the auto road to the top of the summit for breathtaking views of up to 90 miles away. In the fall, the road leading up to Mt. Greylock is shimmering with dense foliage.
In the summer, you could camp at Mt. Greylock Campside Park. Winter is a good time to go snowmobiling on one of the trails leading to the summit.
Bring your camera, especially if you plan on climbing the Veteran Memorial Tower at the top of the summit. Parking is $5 for MA residents and $20 for non-residents.
See a natural white marble arch at Natural Bridge State Park
A visit to Natural Bridge State Park is the best way to learn about glacial erosion in New England. This one-of-a-kind state park has a natural marble arch formed by gushing glacial water over 13,000 years ago.
The park features trails, viewing sections for seeing the natural bridges formed by erosion, a small sculpture park, an old marble quarry, a white marble dam, and waterfalls.
Despite being a small park, it is an ideal spot for a picnic. You could also take a tour with a park ranger to learn about the history of the landscape.
Natural Bridge State Park is open daily from mid-May to early October. Parking for MA residents is $5 and $20 for non-residents.
Take a road trip on Mohawk Trail Scenic Byway, one America’s earliest scenic roads
The historic Mohawk Trail Scenic Byway offers 60 miles of delightful scenery, cultural attractions, and exploration opportunities in Western Massachusetts.
While the Mohawk Trail byway stretches between the Massachusetts New York border and Millers Falls on the Connecticut River, the 37 miles between North Adams and Greenfield on Route 2 in Massachusetts is among the most scenic.
Here’s a fun fact about the byway! It used to be a footpath trade and travel route for Native Americans, and remnants of history are still visible along the stretch.
Popular stops along this route include the Mohawk Trail State Forest, Bridge of Flowers in Shelburne Falls, Poet’s Seat Tower in Deerfield, and the Mohawk Trail’s Hairpin Turn.
The vibrant town of Pittsfield is one of the largest in the Berkshires.
Teeming with arts, and offering a variety of beautiful outdoor spaces, the town is a great place to base yourself while exploring Western MA.
Here are some of the top things to do in Pittsfield and around.
Catch a performance at the historic Colonial Theatre
The historic Colonial Theatre has been consistently hosting musicians, theatre and comic artists, and performers of stature.
Built in 1903, the beautiful 800-seat theatre was meticulously restored in recent years.
Today, Colonial Theatre boasts world-class acoustics, gilded age architecture, and a fine sound and light system.
The Garage, located in the lobby of the theatre, also plays host to regional music performers, storytellers, and comedians.
Watching a performance at the Colonial Theatre is one of the most memorable ways to spend an evening in the Berkshires.
see family-friendly exhibits at Berkshire Museum
The Berkshire Museum is a small, family-friendly museum catering especially to the youth.
With a collection of more than 40,000 objects, they offer a wide range of engaging exhibits.
While the museum offers several rotating exhibits, permanent fixtures like their aquarium, hall of innovation, and animals of the world in miniature are visitor favorites!
Plan on spending a couple of hours at the Berkshire Museum, especially if you plan on taking little ones. Entry is $15/adults and $8/kids aged four and above.
Visit the world’s only round-shaped barn at Hancock Shaker Village
Set on 750-acres in Western MA, the Hancock Shaker Village is one of the oldest and most comprehensively interpreted Shaker sites.
The Shakers trace their origins to Manchester, England. They are believers of Christ’s Second Appearing and arrived in America in the late 17th century.
The Hancock Shaker Village has a working farm, museums, artifacts, and a round stone barn, an architectural marvel built in 1910.
You can easily spend a few hours in the Village. They have gardens, an extensive museum collection, nature trails, a children’s Discovery Barn, craft demonstrations, special exhibits, and events.
Hancock Shaker Village has the oldest working farm in the Berkshires.
In the summer, their farming community holds a series of programs, and guests are welcome to walk through the gardens, see the animals, and interact with farmers and gardeners.
The Village is open from April through December. Entry fee: $20/adult, $8/youth.
Tour Herman Melville’s home
If you’re a literary lover, you’d be delighted to know that Arrowhead, the former home of American author Herman Melville, is also located in Pittsfield, MA.
Melville produced some of his most distinguished works like Moby Dick and Pierre while living and farming on this property.
He named the home Arrowhead after the native artifacts found in the fields.
Today, the home is open during the warmer months for guided visits. 45-minute house and landscape tours are available with knowledgeable guides.
Tours cost $16/adult and $10/student.
Love visiting museums? Here’s a list of 10 more museums that you can visit in the Berkshires!
Admire the natural habitat at Canoe Meadow Wildlife Sanctuary
Located a mile away from downtown Pittsfield, the Canoe Meadow Wildlife Sanctuary is home to wetlands, marshes, flat trails, and quiet wilderness.
Here, you will have the opportunity to spot wildlife and birds too. The sanctuary’s habitats attract warblers, turtles, Ospreys, otters, and the occasional black bear too.
The sanctuary also organizes guided bird walks in the spring and summer. Entry is free, though donations are appreciated.
Camp, hike or plan a picnic at Pittsfield State Forest
With 30-miles of trails and 11,000 acres of forest land, Pittsfield State Forest is an ideal place to visit if you enjoy the outdoors.
Berry Pond, located inside the forest, is one of the highest natural water bodies in Massachusetts. It is also a great camping spot with ample facilities.
If you enjoy panoramas, the view from the top of Berry Mountain is supreme. This is also a great sunset spot. Between April-December, an auto road can take you to the top of the mountain.
Enjoy hiking? Opt for the Tranquility Trail!
Time your visit in June to see twenty acres of wild pink azalea fields in bloom!
Balance Rock State Park
Balance Rock State Park, located in the northeast corner of Pittsfield State Forest is a great add-on attraction to include in your visit.
Here you’ll find a 165-ton boulder balancing itself on bedrock.
The parking fee for MA residents is $5 and $20 for non-residents.
Bike or walk on the breathtaking Ashuwillticook Rail Trail
Located 5 miles north of Pittsfield, the Ashuwillticook Rail Trail is a scenic 12-mile railroad track converted to a well-maintained paved walking and biking path.
The trail passes through the towns of Cheshire, Lanesborough, and Adams.
It provides scenic views of the Hoosic River, mountains, forests, and wetlands.
There are several picnic benches scattered throughout the trail. The surroundings are especially beautiful in the fall, even if you choose not to complete the entire trail.
A must-visit while you’re in the area!
Picturesque Stockbridge is a quintessential New England town in Western Massachusetts.
It is a hub of cultural attractions, with museums, gardens, galleries, and historic homes set against the glorious Berkshires countryside.
A popular weekend getaway for many Bostonians and New Yorkers, Stockbridge, is most renowned for being the home of noted American artist and illustrator, Norman Rockwell.
Starting with the Norman Rockwell Museum, which houses an extensive collection of his works, here are some highlights of Stockbridge that you must check out!
See the original works of legendary painter Norman Rockwell
One of the most popular attractions in the Berkshires, the Norman Rockwell Museum celebrates paintings and illustrations by the legendary American painter, Norman Rockwell.
Rockwell spent the last 25 years of his life in Stockbridge and his studio has been converted into a museum in 1969.
The museum includes 574 original paintings and drawings. Aside from paintings, you can also see Rockwell’s art materials, his library, personal items, and photographs.
Rockwell’s works have been a source of humor and optimism at a time when Americans were dealing with difficult times like the World Wars and The Great Depression.
You can easily spend 2 hours to half a day at this 36-acre site. Many of the artist’s Saturday Evening Post covers can be viewed inside the museum.
If you enjoy the outdoors, there are sculptures, nature trails, fields, and gardens on the museum’s 36-acre property.
Entry to the museum costs $20 for adults and is free for children 18 and under.
To help enhance your visit, download their free app for an audio tour of the museum.
Stroll through Naumkeag’s splendid gardens
For a light adventure, make your way to Naumkeag, a public garden and historic home in Stockbridge.
Another National Historic Landmark, Naumkeag will delight you with its elegant architecture and exquisitely designed gardens and outdoor spaces.
Don’t miss the Blue Steps, a series of deep blue fountain pools, flanked by four flights of stairs and a grove of white birches.
Photo lovers, in particular, will love The Afternoon Garden, Tree Peony Terrace, Rose Garden, Evergreen Garden, and Chinese Garden,
Naumkeag is open for visits from late spring onwards. Entry is $20 for adults.
Be amazed by the variety of plants at Berkshire Botanical Garden
The 24-acre Berkshire Botanical Garden is one of the oldest gardens in the Berkshire region. Described as a “museum of living things,” the garden features an extensive collection of plants native to the northeast.
While you are here, take a moment to look at the Tree of Forty Fruit, created through the process of grafting, which once completed, will grow up to forty heirloom and rare fruits.
Lucy’s Garden is the latest addition to Berkshire Botanical Garden. This is a topiary collection showcasing living plants cut into shapes.
Some of the other highlights in the garden include a Rose and Hosta Garden, a Martha’s Stewart Garden, a Rain Garden, a Children’s Discovery Garden, vegetable and herb gardens, and a European style low maintenance New Wave garden.
While the Berkshire Botanical Garden is open all year round for programs, lectures, and classes, the outdoor display garden is open between May-October.
General admission to the Garden costs $15/adult and is free for children under 12.
Take a leisurely hike on the Mary V. Flynn Trail
Hiking the 1.3-mile Mary V. Flynn trail is an easy activity to pursue with your family.
This scenic, flat and beautiful woodland trail is surrounded by birch trees, pines, and cottonwoods.
The trail passes alongside the Housatonic River and traverses two wooden bridges, meeting the river near a railed section.
If you enjoy a good challenge, opt for the moderately difficult Laura’s Tower Trail. It provides stunning views from the top of a summit.
Dine or stay at the iconic Red Lion Inn
First established in 1773 as a tavern for commuters traveling between Albany and Boston, the Red Lion Inn has undergone several changes over the decades to become one of the most loved luxury hotels in the Berkshires.
The timeless hotel, with a signature red lion on its sign since the 1900s, has played host to five US presidents, authors including Nathaniel Hawthorne, and artists like Bob Dylan.
The Inn offers four different styles of accommodation experiences, and no two lodgings are the same. You could choose to stay in the Main Inn, in tastefully designed rooms with a traditional charm.
Or opt for The Maple Glen, which offers a more modern, countryside vibe.
The hotel has three dining areas and one bar. It is also conveniently located, with access to several attractions within a short distance.
Most known for being the summer home of the Boston Symphony Orchestra, Lenox is an idyllic town that is a popular weekend and vacation getaway for many New Englanders.
Located south of Pittsfield, it used to be an author hub of sorts, being home to Nathaniel Hawthorne, Fanny Kemble, Catharine Sedgwick, Henry Ward Beecher, and Edith Wharton.
Looking for things to do in this lovely town? Below is a starter guide.
Enjoy a thrilling live music concert at Tanglewood
A must attend in Lenox and Stockbridge, Tanglewood Music Festival features a series of classical, contemporary, jazz, and popular music concerts during the summers.
Aside from being the summer performance venue of Boston Symphony Orchestra (BSO) and Boston Pops, Lenox is also home to Tanglewood Music Center, the summer academy for music study, and Tanglewood Learning Institute, which operates year-round.
Between June-August, Tanglewood usually welcomes more than 350,000 guests at its venue.
Since 1938, the festival’s open performance site, The Shed, has been providing concert viewers with sweeping views of Monument Mountain and Stockbridge Bowl in the distance.
Check out the lineup of performances and book your concert tickets in advance.
You could visit the beautiful Tanglewood grounds all year long, free of charge.
ADMIRE the beauty of author Edith Wharton’s home and gardens
Make your way to The Mount, a historic estate designed by noted American author Edith Wharton in 1902.
Wharton is most known for penning the famous novel, “The Age of Innocence.”
The property, a national historic landmark, includes a 19th-century main house, Italian gardens, and stables.
The house and gardens have been immaculately restored and maintained and are a visual treat to the eyes.
To learn more about the history of Wharton’s writings and her humanitarianism, sign up to join one of the guided tours offered by the estate. House tours typically begin in May.
In the winters, you could experience NightWood, an outdoor sound and light experience set against the backdrop of The Mount.
Season permitting, don’t miss a meal at their terrace cafe too.
Entry to The Mount costs $20 for adults. Children under 18 go free.
see a live theatre act at Shakespeare & Company
If you enjoy live theatre, and especially Shakespeare, make sure to reserve tickets for a performance at Shakspeare & Company.
Founded in 1978, Shakespeare & Company has been consistently providing one of the best theatre experiences in the country.
Viewers have particularly enjoyed the theatre’s intimate setting and the company’s fresh take on Shakespeare’s works.
The Company’s new Spruce Theatre is built within and around the trees and provides the perfect environment for a summer afternoon outdoor play.
Take a look at their seasonal line-up and book tickets now!
tour the impressive Ventfort Hall Mansion and Gilded Age Museum
Constructed in 1893, Ventfort Hall, a beautiful Gilded Age mansion indicative of the Jacobean era in New England, belonged to Sarah Morgan.
Sarah was the sister of noted American investment banker J.P. Morgan.
At the time of its completion, it was called “one of the most beautiful places in Lenox.” The house had 28 rooms, including 15 bedrooms, 13 bathrooms, and 17 fireplaces.
While the museum is currently under careful restoration, travelers can get an idea of how beautiful it was at its prime through the intricate woodworking on display.
The museum is open on all days except Wednesdays for self-guided tours, the best way to make the most of your visit is by joining a guided tour.
Tours cost $18/per adult.
Otherwise, audio tours are accessible via smartphones in every room. Be sure to bring earphones.
Planning a long stay in the Berkshires? Read these ideas on more things to do in Lenox MA!
The charismatic town of Great Barrington has slowly become a preferred destination of choice for travelers visiting the highlands of Massachusetts.
Located in the Pittsfield area, at the base of two mountains, the town is home to several small and inspiring boutiques and intimate restaurants serving artisanal cuisine.
Below are some of the best outdoorsy things to do in Great Barrington.
Hike Monument Mountain for impressive views of the Housatonic River Valley
Located at 1,642-feet, the Monument Mountain, offers a distinct viewpoint to observe Mount Greylock, the Housatonic River Valley and the Catskills Mountains.
Located a few miles north of Great Barrington, it makes for an exciting half day adventure.
Did you know that a picnic on Monument Mountain inspired notable author Herman Melville to work on the famous novel Moby Dick?
Follow the footsteps of these literary giants and choose one of the three trails to the top of the summit.
The 1.5-mile Mohican Monument Trail has remains of ancient Native American settlement.
The .83-mile Hickey Trail is the most strenuous route to the summit.
For the best views, opt for the 0.62-mile Peeskawso Peak Trail.
Trails are open from sunrise to sunset. Parking for nonmembers is $6/car.
Enjoy a leisurely Housatonic River Walk
Once a neglegted area between downtown Great Barrington and River Housatonic, the Housatonic River Walk today has an accessible walking path and nearly 200 species of native plants!
To access the path, follow the west bank of the Housatonic River between Cottage Street and Bridge Street.
The upstream section of the trail extends from the River Walk bulletin board at 195 Main Street to the William Stanley Overlook.
The downstream section of the trail commences near the Berkshire Corporation parking lot on River Street and ends at Bridge Street.
Noteworthy stops along the walk include the W.E.B. Du Bois River Park and the William Stanley Overlook.
The trail is free! Here is a map of the access points.
Map – Berkshire Attractions
How to get to the Berkshires
The Berkshires are at a convenient driving distance from both Boston and New York City, making it a family-friendly summer or fall getaway.
In the winter, the region is a popular ski destination as well.
If you’re driving from Boston, you could reach the Berkshires in about two hours if you take the I-90 (Mass Pike). For northern and central Berkshires, take Exit 2 (Lee, MA). For southern Berkshires, take Exit 1 (West Stockbridge, MA)
From New York City, the region is about two hours, forty five minutes away.
From New Jersey, New York City, or Long Island areas, follow any of the parkways north to I-87 North to I-90 East to Exit 2 (Lee, MA).
From the Taconic State Parkway:
- to Northern Berkshires take Route 295 East to 41 North to 20 East to 7 North
- to Central Berkshires take Route 295 East to 41 North to 20 East
- to Southern Berkshires take Route 23 East
The other option is to drive via Connecticut. Take the I-95 N and CT-8 N.
Weather in the Berkshires
Spring in Western Massachusetts is pleasant, with temperatures hovering in the 50s and occasional 60s. Rain showers are common in April and May.
Summers are delightful, and ideal for outdoor activities. Days are long and temperatures hit the 70s and low 80s.
Fall is by far, the most beautiful season in the Berkshires. Temperatures range in the 60s and low 70s.
Winters in New England can be extreme. Temperatures can range in the 30s, 20s, or even below.
Best Time to Visit the Berkshires
Because of its location in the northeast, the Berkshires experience four distinct seasons.
It is a year-round destination, depending on your interests.
The best time to visit the Berkshires is in the fall, followed closely by summer.
Between late September to mid-October, the weather is perfect for hiking, the air is crisp, and the foliage all around is breathtaking. It is also an ideal time to plan a road trip.
June-August is another good time to visit Western Massachusetts when you can indulge in outdoor activities, go berry picking, plan picnics, and enjoy outdoor farm-to-table meals.
In the winters, the outdoors are blanketed in snow. If you’re a skiing or outdoor sports enthusiast, there’s much on offer in the area.
Where to stay in the Berkshires
Wondering where to stay in the Berkshires? You’re in luck! The idyllic countryside setting makes any visit to the region special, no matter the choice of town or stay!
However, depending on your budget type, here are some solid recommendations for inns in the region.
Red Lion Inn: This luxury inn bears the tag of a rich historical past!
Combining old-world charm with modern-day amenities, a stay at the Red Lion Inn is one for the bucket list.
They have a year-round outdoor pool and hot tubs, on-site dining options, luxury linens, and several room categories to choose from.
The inn is also close to several noteworthy attractions, boutiques, gardens, and antique shops.
Apple Tree Inn: The elegant Apple Tree Inn, located on a small hill in Lenox, MA is a great option for travelers hoping to visit Tanglewood or Kripalu.
The inn has a friendly, cozy ambiance and the staff is exceptional.
Many of the rooms have fireplaces and balconies too.
The property has a tennis court, gardens, and a seasonal pool too.
Hampton Inn & Suites Berkshires: With easy access to Tanglewood, Colonial Theatre, and Jiminy Peak Ski Resort, Hampton Inn & Suites Berkshires is a great choice for a stay in the heart of the Berkshires.
Offering free breakfast, a fitness center, an indoor pool, friendly customer service, and several room categories, it is an ideal choice of stay if you’re booking last minute or on a budget.
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Featured Photo Credit: Shutterstock|Romiana Lee