25 Best & Fun Things to Do in Great Barrington MA (Massachusetts)

things to do in Great Barrington MA

Are you looking for the best things to do in Great Barrington, MA? The town is full of great things to do, from its picturesque landscape to its fascinating history and culture.

Whether you’re looking to shop in locally-owned boutiques, sample local brews at microbreweries, or check out world-class art at historic venues, you’ll find all of that and more in this quaint Massachusetts town.

So if you are looking for Fun places to visit in Great Barrington, you will want to check out our list of 26 best things to do in Great Barrington, Massauchusetts.

26 Things to Do in Great Barrington (MA)

#1. Riverside Park

things to do in Great Barrington MA

The Great Barrington Riverway is the 1st on our list of things to do in Great Barrington, MA. It is a short walk away from restaurants and shops in downtown Great Barrington.

The park features a 1.5-mile walking path along the Housatonic River and has several stone bridges that cross over it. Popular spots to visit nearby include Mill House Park and a recreational boat ramp at Pontoosuc Lake.

There’s also plenty of fishing opportunities on the Housatonic River and its tributaries. You can book guided trips or rent fishing gear from local outfitters if you don’t have your own rod and reel.

Don’t forget to bring cash because there are no ATMs available near Riverside Park.

#2. Mass MoCA Museum

things to do in Great Barrington MA

The Mass MoCA museum is one of the things to do in Great Barrington (MA). It’s a renovated former industrial facility that’s home to a world-class museum and a live music venue.

You can check out over 400 modern art installations there, like Early 21st Century Drawing Room. The museum boasts that it’s One of America’s best destinations for creative people who want active encounters with visual and performing arts.

In addition to their permanent collection at their two galleries (and outdoor sculpture garden), they also regularly host both local and international artists.

There are over 300 exhibitions each year, so if you love art or want something else to do while you’re visiting Great Barrington, be sure not to miss it! And did we mention it’s free? For a fun time, this museum is one of the best places to visit in Great Barrington, MA.

Address: 87 Marshall St., North Adams, Massachusetts

#3. Berkshire Botanical Gardens

things to do in Great Barrington MA

Berkshire Botanical Gardens is a gorgeous scenic spot with an array of flora; it’s also home to a summer concert series and various other events.

The gardens are open all year round for exploration, although visiting during warmer months will give you more flowers and greenery to admire.

If you want something unique that doesn’t involve hiking or camping, consider adding a visit here—it’s one of those must-sees if you live near Berkshire County.

Plus, there’s a small gift shop on site where you can purchase plants and other items to take home as souvenirs.

Address: 5 W Stockbridge Rd, Stockbridge, MA 01262

#4. Monument Mountain

things to do in Great Barrington MA

Most visitors come to Great Barrington (MA) seeking a quiet and scenic getaway from Boston or New York City.

You’ll find it at Monument Mountain. Located near Mount Greylock in north-central Massachusetts, about two hours from Boston and one hour from Albany, NY, Monument Mountain is best known for its hiking trails.

It stretches for more than 12 miles through forests and across open meadows and rock ledges that provide stunning views of the surrounding mountains. Be sure to add this to your list of things to do in Great Barrington MA.

Address: Great Barrington, MA 01230

#5. Ski Butternut

things to do in Great Barrington MA

Great Barrington is home to Butternut Ski Area, which offers skiing and snowboarding for beginners through experts.

The mountain has an impressive vertical drop of 1,300 feet. Ski Butternut also offers four terrain parks featuring jumps, rails and boxes with progressive features including a half pipe.

There are also trails specifically designed for kids ages five to 12 as well as terrain features that allow beginners to practice parallel turns at their own pace.

To ensure skiers remain safe on slopes with variable levels of experience, Great Barrington has ski patrols on duty every day from 9:30am until 4:30pm during winter months.

In addition to all these great things, there’s plenty more going on at Great Barrington—it’s definitely worth visiting if you’re looking for things to do in Great Barrington (MA).

Address: 380 State Rd, Great Barrington, MA 01230

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#6. The Norman Rockwell Museum at Stockbridge

things to do in Great Barrington MA

The Norman Rockwell Museum is located at 9 Glendale Road in Stockbridge and is surrounded by three gorgeous Berkshire mountains.

Although it’s primarily a museum for Rockwell’s artwork—most of which was drawn during his time as a painter for The Saturday Evening Post—the museum also offers guided tours of his former home and grounds.

When you visit, be sure to check out The Art World, which documents many of Rockwell’s most famous works; The Library, which showcases more than 60 editions of The Saturday Evening Post; and The Studio, where you can see what he worked on (and still works on) every day.

If you’re lucky, you might even catch him working! As an added bonus, there are often special events that take place throughout the year.

For example, there is an annual Jazz Brunch held each spring that features live music from local musicians.

If you want to learn more about other fun things to do in Great Barrington (MA), Visit Norman Rockwell Museum today!

Address: 9 Glendale Rd, Stockbridge, MA 01262

#7. The Guthrie Centre & Foundation

things to do in Great Barrington MA

The Guthrie Center and Foundation runs a library, a bookstore, and a sculpture park. In addition to its artistic community, Great Barrington also has a thriving downtown area with restaurants and shops galore.

Perhaps you’d like to explore all that Berkshire County has to offer? If so, visit Monument Mountain for hiking or biking (or both!).

There are also plenty of vineyards nearby if you feel like getting sauced! Be sure to add this to your list of things to do in Great Barrington, Massauchusetts.

Address: 2 Van Deusenville Rd, Great Barrington, MA 01230

#8. Mahaiwe Performing Arts Centre

things to do in Great Barrington MA

Performing artists and musicians know just how important it is to get their name out there. The Mahaiwe Performing Arts Centre in Great Barrington (MA) is one of those places that gives local talent a chance to perform.

Whether you’re interested in contemporary music or ballroom dancing, you’ll find an event taking place at Mahaiwe; just check their schedule for more information.

The Mahaiwe was founded in 1989 by a group of local entrepreneurs who were passionate about preserving theater history in New England.

It offers top-notch lighting and sound equipment as well as professional staging capabilities, so whether you’re a musician or theater enthusiast, it’s worth checking out!

Address: 14 Castle St, Great Barrington, MA 01230

#9. Taft Farms

things to do in Great Barrington MA

If you’re looking for a fun and educational place for kids, look no further than Taft Farms. This lovely location provides outdoor activities like canoeing and picking apples.

Taft Farm is a small, family-owned farm that has been serving the Berkshire community for over 50 years. Taft Farm is tidy and well looked after by its owners.

Once you’ve toured the beautiful green farm, explore some of Taft Farm’s other great amenities such as trying your hand at farming or shopping for fresh produce.

As far back as 1961, Taft Farm has participated in the world of sustainable farming and generous harvests. It is one of the best activities to participate in when visiting Great Barrington.

Address: 119 Park St, Great Barrington, MA 01230

#10. Lake Mansfield

things to do in Great Barrington MA

Take a walk around Lake Mansfield. The lake is an idyllic spot for strolling with its beautiful views of Mount Greylock and Mansfield Hollow Lake.

If you’re lucky, you might even see some wildlife such as deer or birds like loons and ducks (be sure to bring your camera).

There are many hiking trails near by that can take you through forests or along scenic lakes. Once winter comes, cross-country skiing will be available on most of these trails so it’s best to check online before heading out if you don’t want your trip ending early.

Check out nearby Guthrie Mountain Ski Area for more details on their locations and hours! While you are in Great Barrington, stop by Lake Mansfield and embark on a 0.25-mile forest hike in your hiking clothes.

A pleasant trail awaits. Lake Mansfield has many of the best things to do in Great Barrington.

#11. Housatonic River Walk

things to do in Great Barrington MA

The river walk is a perfect way to get some fresh air and enjoy nature. This walking trail runs along the Housatonic River, stretching from Lake Lillinonah down towards East Street.

It’s an enjoyable walk with plenty of natural beauty and wildlife. You’ll also pass by several parks and waterfront restaurants on your walk as well. And since it runs along two miles of highway, you can travel at whatever pace you like without worrying about cars or bikes.

If you do want company though, consider booking one of Shuttleworth Tours’ sunset cruises down the river—they feature live entertainment and cocktails for adults!

You can also book a private cruise for weddings or other special events if you prefer that kind of thing!

Address: 7 Cottage St, Great Barrington, MA 01230

#12. Windy Hill Farm

things to do in Great Barrington MA

Have you ever been to a botanical garden or farm? You should visit Windy Hill Farm in Great Barrington.

Windy Hill Farm is a horticultural business with diverse plants, and the farm has served Berkshire County and other neighboring counties in Massachusetts.

A windy hill farm has an apple orchard, a retail garden center, a blueberry field, and field-grown specialty ornamental nursery stock.

There’s a horticultural farm in this location that was established over 28 years ago, it produces the species of ornamental trees, fruit trees, and small fruits; shrubs, grasses, evergreens of different types; conifers and broadleaf varieties. vines; hardy bush roses, and more.

You will also find all sorts of interesting native fruits as well as old favorites, so come to Windy Hill Farm for a thrilling day of harvesting and learning about making sculptures out of the fruit and keeping fruit trees at home.

One of the best things to do in Great Barrington is pick or pluck fruits at Windy Hill Farm. And whether your visit is for an event with friends or with family, you’ll have an amazing horticultural experience at Windy Hill Farm.

Address: 686 Stockbridge Rd, Great Barrington, MA 01230

#13. Fountain Pond State Park

things to do in Great Barrington MA

You can find an interesting state park called “The Fountain Pond” at the Berkshire South Regional Community Centre.

The park has pine trees, steps, boardwalks, bridges, trails, and different kinds of plants like mushrooms and wildflowers.

To notify the Berkshire South Regional Community of your intention to use the park’s rope course or other equipment, follow the stone steps.

Turn right at the tree line, and continue until you find the kiosk.Before going on the Trail, prepare yourself by mentally or physically by mentally or physically; there are very large shrubs and vines before coming across rocky outcroppings and wetlands; there are boardwalks and bridges later on the trail.

Once you reach the double-bough bridge, you have hiked halfway through the journey.The idea here is to enjoy yourself while adventuring in the park, even if you have to go around the long trail route and use route seven.

Hiking through the Fountain Pond State Park is one of the fun things to do in Great Barrington.

Address: US-7, Great Barrington, MA 01230

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#14. Berkshire Playwrights Lab

things to do in Great Barrington MA

If you’re looking for a more intellectual, laid-back trip, head down Main Street to the Berkshire Playwrights Lab. The BPL is dedicated to discovering and nurturing playwrights who contribute original works of art.

Offering workshops and assistance with various writing projects including plays, musicals and adaptations of classic novels, it’s easy to see why BPL has garnered quite a bit of attention over its 15-year existence.

There is always something for you to enjoy when you go to Berkshire Playwrights Lab – such as readings, workshops, and staged productions to relay the works of playwrights to the audience, who is invited to watch plays or listen to a story, which are written by their authors.

Address: 352 Main St #202, Great Barrington, MA 01230

#15. Vault Gallery

things to do in Great Barrington MA

The Vault Gallery is a unique art gallery located on Main Street. It has pieces by both emerging and established artists from all over.

The price range varies as does genre and style of work, but every piece is fascinating. If you are looking for an intimate setting for a conversation with friends or art lovers who just love to look at beautiful paintings, it’s a great place to spend an afternoon!

The Vault also features concerts that occur once a month and poetry readings hosted by members of their community.

Their focus is on local artists, so if you’re into that sort of thing, definitely check out their website or call them up!

Address: 322 Main St, Great Barrington, MA 01230

#16. The Emporium Antiques & Art Center

things to do in Great Barrington MA

Do you enjoy art? Are you interested in glass art? We would also suggest that you visit the Emporium Antiques & Art Centre in Great Barrington, Massachusetts.

At Emporium Antiques & Art Centre, we offer the widest selection of Loetz glass in Massachusetts and outside. You will find the most exquisite glass and antique works at the antique store and art center, and many are of museum quality.

Numerous antiques, like furniture, jewelry, accessories, ceramics, and many more, are displayed in the exhibition halls. Perhaps when you visit, you will get lucky and find a ceramic beer stein, which is roughly four to five feet high.

In addition, you’ll see butterflies inside framed pictures at the art center.One of the best activities in Great Barrington is visiting Emporium Antiques & Art Center.

Address: 162 Main St, Great Barrington, MA 01230

#17. Housatonic Flats Trail

things to do in Great Barrington MA

The Housatonic Flats loop is a 0.9-mile trail perfect for new hikers or family-oriented excursions. With this trail, you’ll discover 26 acres of the Housatonic Flats.

If you’re seeking a sacred experience with wildlife in the Mohican Hills, hiking at Housatonic Flats may be for you. When hiking in this area, it is likely that you will be lucky enough to spot deer, fish in the river, otters, and many species of birds along the way.

Have fun as you explore this trail and as you happen to find more animals and birds.One of the best things to do at the Housatonic Flats in Great Barrington is wildlife watching or birdwatching.

Address: 439 Stockbridge Rd, Great Barrington, MA 01230

#18. Saint James Place

things to do in Great Barrington MA

If you’re an outdoorsy person, then you’ll be happy to hear that there are tons of things to do in Great Barrington, MA. Right on Eagle Street is Saint James Place.

At St. James Place sits across from fire station and right next door is a playground for kids and families just like yours!

Enjoy a picnic with family or friends at St. James place while your children play safely nearby. You can even walk over towards park benches if you want a quiet moment away from all of your fun!

Plan an entire day of fun by starting at Saint James Place where you’ll find plenty of room for games and great people watching!

When it comes time to pack up and head home, you won’t have far to go! Head back towards town via Church Street and make sure to stop in one of the many shops along the way.

Address: St James PlGreat Barrington, MA 01230

#19. Asia Barong Gallery

things to do in Great Barrington MA

A cultural refuge that offers some of the finest work by Southeast Asian artists. The gallery also hosts weekly Thai language lessons and frequent concerts and performances.

If you’re looking for something a little offbeat while visiting, Asia Barong is an experience worth checking out. When you visit Great Barrington, Massachusetts it is easy to see how it has earned its reputation as a quaint artsy town.

There are plenty of shops and galleries where you can find amazing local art. Be sure to check out Asia Barong Gallery on your next trip.

Address: 199 Stockbridge Rd, Great Barrington, MA 01230

#20. Yellow House Books

things to do in Great Barrington MA

One of Great Barrington’s most beloved bookstores is Yellow House Books. In business since 1967, it offers a mix of used and new books and has even won multiple local awards for its stock.

Nearby activities include hiking nearby trails like Pond View Trail and visiting W.E.B. Du Bois’ grave site at Mount Hope Cemetery just 10 minutes from town.

Yellow House Books is a three-room bookstore and library in Great Barrington that has a wide selection of used and rare books sorted by genre and type.

Here at Yellow House Books, you will find music books, arts books, photography books, do-it-yourself books, and books for inspiration.

Additionally, there are a few children’s books for different ages and books for adults in self-help areas. You will also find many other genres of books, such as mythology, metaphysics, religion, and philosophy, in the bookstore.

If you want to stop by on a Saturday morning for live music or poetry readings, go for it! While there are countless things to do in Great Barrington, MA, don’t miss out on one of the city’s most treasured stores: Yellow House Books. You’ll be glad you did.

Address: 252 Main St, Great Barrington, MA 01230

#21. The Well Restaurant

things to do in Great Barrington MA

One of the nicest things to do in Great Barrington is to dine at the Well Restaurant.

The Well Restaurant is a lovely establishment with a wide range of cuisine. When you visit the restaurant, go through the menu and sample the delectable specials.

When you approach the eatery, you have the option of staying in the outdoor or inside area. The Well Restaurant offers a relaxing atmosphere in which to enjoy a nice dinner with family or friends. There are both indoor and outdoor seating options at the restaurant.

The Well Restaurant is open from 4 p.m. to 8 p.m. Wednesday through Saturday, and it’s a great spot for a romantic dinner with your friends and family. If you don’t want to remain at the restaurant, you can order takeaway.

Address: 312 Main St, Great Barrington, MA 01230

#22. Jameson Limited Reserve

things to do in Great Barrington MA

In Europe and America, Jameson Limited Reserve produces unique whiskey in hand-selected oak barrels.

This excellent whiskey boasts a complex flavor profile of vanilla, oak, spice, and toffee, which is owing to the unusual procedure utilized to make these wines.

Angel’s Envy Kentucky Straight Bourbon, for example, is a Jameson Limited Reserve alcoholic beverage that has garnered honors. The handmade bourbon is thoroughly conditioned, mixed, and processed in each batch.

When you visit the Jameson Limited Reserve, you’ll get a taste of a distinctive, rich, and smooth whiskey. One of the best things to do in Great Barrington is visit the whiskey reserve.

#23. Bernay Fine Art

things to do in Great Barrington MA

Bernay Fine Art is a modern art gallery in Great Barrington that features works in a variety of media, including painting, glass, sculpture, ceramics, and more.

The art gallery also hosts local and tourist art displays and exhibitions.Bernay Fine Art features artwork from artists from all around the globe, as well as pieces by Berkshire artists.

Explore Bernay’s fine art gallery when visiting Great Barrington with your family or friends. Bernay Fine Art represent the one-of-a-kind works of renowned artists working in a variety of mediums.

Address: 296 Main St, Great Barrington, MA 01230

#24. Guido’s Fresh Marketplace

things to do in Great Barrington MA

Are you looking for the best market place to shop your veggies, fruits, flowers, meat, seafood, fresh farm goods, and many other things? Well, Guido’s Fresh Marketplace is a top notch market.

It is a family owned and operated company that the family runs and manages. At the independent marketplace, you will also discover freshly cooked items that are ready to eat. Bring your friends and family to the market for a fun-filled day of grocery shopping.

The marketplace is a lovely area to shop for groceries, and the personnel is polite and happy to help you with your purchases.

One of the fun things to do in Great Barrington, MA is to go grocery shopping at Guido’s Fresh Marketplace.

Address: 760 S Main St, Great Barrington, MA 01230

#25. Lauren Clark Fine Art

things to do in Great Barrington MA

Lauren Clark Fine Art is another fantastic contemporary art gallery in Great Barrington that features works by more than 40 local and international artists.

Paintings, sculptures (indoor and outdoor), fine art prints, pictures, jewelry, pottery, and other artworks may be found when you visit the lovely art gallery with your friends and family.

One of the best things to do in Great Barrington, MA is to look through the artwork at Lauren Clark Fine Art. Local artists may share their experiences and artwork inspirations in the fine art gallery’s community of artists.

You may bring your images to Lauren Clark Fine Art for expert framing. These framings are created by artists using one-of-a-kind materials that will endure a lifetime.

For over 30 years, the fine art gallery has been framing paintings and other works of art. Bring your family and friends to this modern art gallery for a relaxing evening of art.

Address: 684 Main St, Great Barrington, MA 01230

Plan Your Trip to Great Barrington Today!

If you are searching for things to do in Great Barrington, MA, this article has everything you need to know. It’s an excellent place for visitors and locals, and the weather is always perfect.

Great Barrington is the perfect destination for people who love adventures. With an array of attractions and activities, it’s no wonder that it has become the fastest-growing city in Mass.

So, start preparing to tour Great Barrington on your next vacation. You’ll love it and enjoy the places to visit in Indiana.

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