Blake Walsh

15 Best Things to Do in Great Barrington, MA

  • Published 2021/10/08

Located along the Housatonic River within Berkshire County, Great Barrington, MA, offers a small-time charm that repeatedly attracts many visitors, especially from nearby areas.

Apart from breathtaking nature, the area’s peacefulness offers people from busy cities a respite from their fast-paced life.

With many walking trails, art galleries, and historically significant sites, this place is worth visiting.

Here are some of the best things to do in Great Barrington, MA:

Walk the Trails up Monument Mountain

View of Monument Mountain

Dan Hanscom /

Many locals and tourists deem Monument Mountain as one of the most popular destinations in Great Barrington.

The place itself has inspired many artists, including poets and authors such as Nathaniel Hawthorne and Herman Melville.

In fact, after a picnic and an incident up this mountain, Melville got the ideas he needed to create the famous book “Moby-Dick.”

View of Monument Mountain

Dan Hanscom /

Today, this mountain attracts over 20,000 hikers who can explore the area and discover amazing views.

If you want to visit Monument Mountain, you can choose among three popular hiking trails. The first one, the Mohican Monument Trail, spans 1.5 miles and lets you pass by the remain of routes used by Native Americans.

The other two are Hickey Trail (0.83 miles) and Peeskawso Trail (0.62 miles).

Discover Impressing Pieces at Bernay Fine Art

Established in Chicago, IL, 13 years ago, Great Barrington has become the home of Bernay Fine Art since 2019.

Here, you will find both traditional and non-traditional art that will impress anyone who sees them.

It has a collection of pieces made in different media, such as paintings, sculptures, photographs, pottery, and art on paper.

If you want to find a place where you can appreciate high-quality art pieces, check out Main Street in Great Barrington and step into Bernay Fine Art.

Have Fun in the Snow at Ski Butternut

Fancy a skiing trip in this part of the Berkshires?

Located on Warner Mountain in Great Barrington, you can head over to Ski Butternut with your family for some fun in the snow.

It has a skiable area spanning 110 acres.

Kids can ski through a good one-fifth of that area.

Beginner skiers to experts can find a fantastic place to ride through here, and the site offers rentals for everything you might need.

The place also offers lessons for beginners as well as 11 lifts for the convenience of tourists here.

For a winter wonderland out in the Berkshire, head over to Ski Butternut.

Stroll Along the Housatonic River Walk

You don’t have to worry about missing out on exercise when you visit Great Barrington, as exploring many of its outdoor attractions can provide you with the caloric burn you might need.

Among the many trails that you can find here, consider exploring the Housatonic River Walk.

You can find this greenway trail running along the west bank of the Housatonic River, which cuts through the downtown area of Great Barrington.

View of Housatonic River Walk

John Phelan, CC BY 3.0, via Wikimedia Commons

In particular, you can find this popular River Walk in between Cottage St. and Bridge St.

Throughout history, this river has been abused as it was neglected and utilized to carry industrial waste.

However, as many as 2,200 local volunteers have continuously worked hard to restore its beauty.

When you follow this path, you not only experience a state of tranquility, you can also see how the volunteers’ efforts have made it possible to reclaim this river’s beauty.

If you feel like going on a stroll or a jog and getting some exercise while in Great Barrington, why not check this place out?

Discover Nature at Pfeiffer Arboretum at Long Pond

Do you happen to prefer less crowded, quieter areas to appreciate the nature existing at a specific locale?

Try exploring the Pfeiffer Arboretum at Long Pond.

Many deem this as one of Great Barrington’s hidden gems.

This 0.7-mile property features a looping walkway that goes through an impressive forest and wetland.

The forest management group that handles the preservation of this place makes sure to control the invasive species of flora here to keep the population of native plants here healthy.

While on the shorter side when it comes to walking trails, this arboretum makes up for the natural scenery that you can witness as you stroll through it.

From the gorgeous vegetation that you can see all around to the fantastic views of Long Pond, head to this place to appreciate the beauty of nature and for some peace and quiet.

Pay a Visit to Guthrie Center and Foundation

The Guthrie Center and Foundation aim to become a place where individuals can come together for spiritual services and the exchange of knowledge and cultures.

Arlo Guthrie established this place back in 1991 as an Interfaith Church.

Today, it also hosts various cultural programs that many locals and tourists can see themselves as a part of.

The center houses a Musical Instrument Library, where you can check out and borrow a few to try out or to practice with.

It also features some exhibits connected to the history of this foundation and some memorabilia of the Guthrie Family.

It’s a great place to check out while you’re in Great Barrington.

Appreciate Performances in Mahaiwe Performing Arts Center

View of Mahaiwe Performing Arts Center

Anc516, CC BY 3.0, via Wikimedia Commons

Many people visit Great Barrington for the Mahaiwe, which aims to promote performing arts in the Berkshire area.

Here, you will find that the center offers an array of programs tackling the various forms of performance arts – from dance and music to theater.

As a visitor of the Berkshire area, you can catch one of their excellently produced shows.

A gorgeous, historic theater serves as the venue for these performances, and it adds something magnificent to your experience of the show.

The center itself aims to produce shows that will entertain audiences of all ages, so you and your companions could catch a performance of your liking while you’re in town.

Check Out Taft Farms

While visiting Great Barrington, don’t forget to check out the charming Taft Farm.

For more than 50 years, this farm has dedicated itself to sustainable farming, and the bountiful harvest they constantly experience proves that it works.

When you visit the site of this farm, which has stood there since 1961, you can learn how to operate their farm and shop for some of the best products around.

During your visit, makes sure to check out their kitchen and deli for some delicious dishes.

Want to learn something about how they farm?

Consider checking out their greenhouse as well.

Have Fun in Lake Mansfield

Featuring a pond and a forest, both spanning 29 acres, you can reach the Lake Mansfield Recreation Area for some outdoor fun with your family.

Here, you and your companions can frolic around the shores of the lake and the nearby forest to stay active and make memories of having fun while staying among nature.

While visitors can come here, you also need to be mindful of your impact on the delicate ecosystem and habitat this place provides.

Apart from the lake’s beach area, you can also explore the 0.25-mile walking trail within the forest.

Learn About the Life of W.E.B. Dubois at Du Bois National Historic Site

View of Du Bois National Historic Site

Daniel Case, CC BY-SA 3.0, via Wikimedia Commons

A National Historic Landmark found right in the city; many know the W.E.B. Du Bois Homesite is an important place for a historically significant person.

It serves as the home of civil rights activist W.E.B. DuBois for the first five years of his life.

Originally owned by his grandfather, Du Bois received the house in 1928.

It received its National Historic Landmark status in 1976.

What you need to know, however, is that this place is not exactly a museum.

It’s a walking trail, with plaques educating people about this man’s life dotted along its path.

If you happen to be interested in significant historical people hailing from Great Barrington, check this place out.

Find Old-Fashioned Sweets at Robin’s Candy Store

What’s unique about a candy shop?

While not many places would even consider a candy store as a part of their “best things-to-do list,” Robin’s Candy Store offers its patrons something special.

This shop will satiate your sweet tooth with all the delicious treats that they offer.

However, if you have a favorite flavor or type of candy from your childhood or want to try out sweets from yesteryears, this is the place to be.

Apart from modern confections, Robin’s Candy Store offers old-fashioned sweets as well.

If you’re curious and want to try those out, make sure to stop by this exciting candy store.

Be Impressed by Asian Art at AsiaBarong Gallery

When traveling to Great Barrington, you don’t expect to find intricate Asian art pieces.

However, the city serves as the home of Asia Barong, a museum-gallery hybrid featuring the most exquisite traditional art pieces from Asia.

Here, you can explore and find a lot of interesting pieces, get to know more about this style of art, and even educate younger kids about other cultures in the world.

Featuring stunning ethnographic art, stepping into this gallery feels like you walked into a different part of the Earth.

Additionally, when you visit this place, you also get to help out the Asian artists from that part of the world who have made the pieces featured here.

Spend some time here and discover a vibrant and interesting culture from a continent thousands of miles away.

Other Things to Do Nearby

Head Over to Norman Rockwell Museum

View of Norman Rockwell Museum

James Kirkikis /

Located just 15 minutes out of Great Barrington, you can find the Norman Rockwell Museum in Stockbridge.

Here, you can find the works of the artist it’s named after, including a permanent collection featuring more than 900 of his original creations.

View of Norman Rockwell Museum


Within the last years of his life, Rockwell bequeathed his studio in the city to the said museum, and you can find it here, arranged as to how it was set up.

Apart from Norman Rockwell’s works, you can also find exhibits that feature pieces tackling different parts of this extraordinary artist’s life.

Discover Beautiful Flowering Plants at Berkshire Botanical Gardens

View of Berkshire Botanical Gardens

Theresa Lauria /

If you appreciate beautiful flowering plants and impressive trees, heading to Berkshire Botanical Gardens should join your to-do list.

Located just 17 minutes away, in Stockbridge, this attraction features a vast, historic garden created in 1934.

The property spans 15 acres, with different areas featuring a distinct seasonal palette.

View of Berkshire Botanical Gardens

Theresa Lauria /

Apart from the breathtaking gardens, you can also explore the area and find three houses made of glass, the garden’s educational center, and a few art galleries.

Guided tours through the property are available, and consider booking one to learn more about the place.

Experience the Thrill at Catamount Aerial Adventure Park

If you want to spend time taking part in thrilling activities with your friends, head over to Catamount Aerial Adventure Par.

Here, you can find several canopy walk courses that are both exciting and awe-inspiring.

There are also aerial platforms that you can explore and reach through various thrilling ways, including ziplining and rope walking.

It’s a family-friendly place where you can have a lot of fun, trying out challenging outdoor activities with your loved ones.

Be Inspired by The Mount

View of The Mount


The former home of the outstanding author Edit Wharton, you can check out the gorgeous estate in the Berkshires called The Mount.

This place features elegant and intricate architecture and decor, partnered with a fantastic garden that Wharton herself designed.

View of The Mount


When you come here, apart from admiring the place, you can learn more about the life of this famed author.

You can also find walking trails, a cafe, and a bookstore within the estate.

Located just 21 minutes away from Great Barrington, The Mount in Lenox is definitely worth the visit.

Final Thoughts

Through the years, Great Barrington and the Berkshire area, in general, have enjoyed a surge in popularity among tourists nearby.

Given its charm and amazing ambiance, this increase in popularity makes sense.

If you want to find out what allure this town has, why not visit and see it yourself?

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