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

In search of the best and most fun things to do in Great Barrington, MA?

Great Barrington is a small town in Berkshire County, Massachusetts, United States. The city lies along the Housatonic River within Berkshire County.

The town is also a part of the Pittsfield, Massachusetts, Metropolitan Statistical Area. The small peaceful town was the home of the Mahican Native Tribe. The Mahican Indians named Great Barrington Mahaiwe, meaning “the place downstream.”

Great Barrington is a very peaceful town with many galleries, historical sites, and natural habitats, and these features attract a lot of visitors from all over the world.

Great Barrington creates a safe haven from the city’s busy life with an extraordinary and slow-paced life. Here are the top attractions in Great Barrington, Massachusetts.

Things to Do in Great Barrington

1. Monument Mountain

Monument Mountain
Credits: L.A. Nature Graphics / Shutterstock
Monument Mountain

Monument Mountain has been one of the top attractions in Great Barrington that has attracted people and hikers from worldwide. The mountain has an elevation of 1,642 feet and gives a stunning view of the beautiful landscape of Housatonic River Valley from the mountain summit.

In the 19th century, Monument Mountain served as an inspiration for many literary giants; books, poems, and other literary works were written about Monument Mountain. Even painters and other artworks were made referencing the mountain.

One literary piece inspired by the mountain is Herman Melville’s book, Moby-Dick, inspired by a picnic hike on the hill with Nathaniel Hawthorne in 1850. The book was later dedicated to Nathaniel Hawthorne.

Hiking on Monument Mountain is one of the best things to do in Great Barrington.

Address: Route 7, Great Barrington, MA 01230

2. Ski Butternut

Ski Butternut
Credits: Lukas Gojda / Shutterstock

Enjoy skiing in Great Barrington with your friends and family at Ski Butternut. This is one of the fun things to do in Great Barrington, MA.

Ski butternut is a beautiful place to go skiing with your friends or family, have fun in the snow, and experience a beautiful adventure during winter when you visit Great Barrington. Ski butternut offers specific fun snow areas according to your skill.

There is a separate ski area for beginners and experts to have fun. Ski Butternut has about 110 acres of skiing area, and one-fifth of the site is suitable for kids to ski. At ski Butternut, there is something for everyone to enjoy.

Ski Butternut also offers lessons for beginners and 11 lifts for tourist convenience. So head on to Ski Butternut with your friends and family when you visit Great Barrington during winter.

Address: 380 State Rd, Great Barrington, MA 01230-1463

3. The Guthrie Centre & Foundation

Guthrie Centre & Foundation
Credits: The Guthrie Center / Facebook
Guthrie Centre & Foundation

Guthrie Centre & Foundation is a center for cultural preservation, promoting educational achievement, and fostering community outreach to meet the community’s ongoing needs. Guthrie Centre & Foundation is known for interfaith worship and cultural exchange using music and art.

The Centre was founded by Arlo Guthrie but was named after his parents, Woody & Marjorie Guthrie, in 1991 to honor his parents. The Guthrie Centre & Foundation holds a historical event that makes here relevant and a place of reflection.

Asides from worshiping and promoting culture, the Centre is also a place to eat and enjoy performances at the Old Trinity Church, where the Guthrie Centre & Foundation is located. So take your friends to this Centre to enjoy learning, meeting new people and having fun.

Address: Old Trinity Church 2 Van Deusenville Road, Great Barrington, MA 01230

4. Mahaiwe Performing Arts Centre

Mahaiwe Performing Arts Centre
Credits: WinWin artlab / Shutterstock

Mahaiwe Performing Arts Centre is a harbor of theatrical performances in Great Barrington. The Centre aims to present performing arts, film, educational, and family programs all year round for the Berkshires and other neighboring communities.

Get entertained at Mahaiwe Performing Arts Centre as you watch great performances of very talented performers through dance, music, theatre, and opera. As you watch, note your best acts on stage and engage with the audience.

Watching theatrical performances at the Mahaiwe Performing Arts Centre with your friends or family is one of the best things to do in Great Barrington, MA, so do add to your bucket list.

Address: 14 Castle St, Great Barrington, MA 01230-1513

5. Taft Farms

Taft Farms
Credits: xoverian / Shutterstock

Explore Taft Farms to learn more about farming and try out farming with your friends and family in Great Barrington, Massachusetts.

Taft Farm is a small family-owned farm that has served the Berkshire community for over 50 years. The farm is neat and well catered for by its owners. Walk around the beautiful green farm and explore other unique parts of the farm.

When you visit Taft farm, you will learn how to operate their farm and shop for fresh farm produce. Taft farm has consistently engaged in sustainable farming and bountiful harvest since its establishment in 1961.

Be sure to visit Taft Farm when you come to Great Barrington as it is one of the best things to do in Great Barrington.

Address: 119 Park St N Route 183, Great Barrington, MA 01230-1135

6. Lake Mansfield

Lake Mansfield is a 29-acres recreational area featuring a pond and forest. Lake Mansfield is a great nature area to relax and spend time away from the city.

Enjoy a picnic near the lake’s beach area while talking with friends or family. Stroll through the forest paths with your partner, or you can sit and bask in the beauty of the site. Hiking is also an excellent activity to do while at Lake Mansfield.

At Lake Mansfield, you will find a 0.25-mile trail within the forest area, get on your hiking clothes, and hit the trail with your hiking partner to explore the beautiful green forest. Hiking at Lake Mansfield is one of the fun things to do in Great Barrington.

7. Housatonic River Walk

Housatonic River Walk
Credits: Anetlanda / Shutterstock

The Housatonic River Walk is a must-visit among other trails in Great Barrington. Taking a walk on the Housatonic River Walk is one of the top things to do in Great Barrington.

Housatonic River Walk is a greenway trail that runs along the west bank of the Housatonic River, cutting through the downtown area of Great Barrington. The trail is a perfect place to enjoy outdoor exercise. You can walk, run, or jog around the neighborhood alone or with your friends.

The community of Great Barrington has worked earnestly to protect and restore the beauty of the Housatonic River area, and the area is neat with a serene environment. Housatonic River Walk is also a great place to enjoy tranquillity and serenity.

Address: 195 Main St, Great Barrington, MA 01230-1602

8. Windy Hill Farm

Windy Hill Farm
Credits: nadia_if / Shutterstock

Have you ever visited a horticultural site with many fruits, flowers, and other plants? If not, you should see the Windy Hill Farm in Great Barrington.

Windy Hill Farm is a horticultural operation with diverse plants, and the farm has served Berkshire County and other Counties in Massachusetts. You will find an apple orchard at the Windy Hill farm, a retail garden center, a blueberry field, field-grown specialty ornamental nursery stock, etc.

The diverse horticultural farm has been in existence for over 28 years and has served the varieties of specimen and flowering trees; tree fruits and small fruits; ornamental shrubs and grasses; conifers and broadleaf evergreens; vines; hardy shrub roses, and so many more.

You will also find native species and traditional favorites; visit Windy Hill Farm for an exciting day of plucking fruits and learning about small fruit design, design and installation, and home orchard.

Picking or plucking fruits at the Windy Hill Farm is one of the fun things to do in Great Barrington. Have an amazing horticultural experience with friends and family visiting Windy Hill Farm.

Address: 686 Stockbridge Rd, Great Barrington, MA 01230-1270

Also, check out our list of things to do in Hyannis, and attractions in Worcester for a fun time in these cities of Massachusetts.

9. Fountain Pond State Park

Fountain Pond State Park
Credits: antstang / Shutterstock

The Fountain Pond State Park is a fun state park located at Berkshire South Regional Community Centre; the park features a pine forest, stone steps, boardwalks and bridges, trails, and different plants such as mushrooms and wildflowers.

While at the park, be sure to inform the Berkshire South Regional Community before using the rope course or any other equipment in the park. To find the stone steps follow the trailhead toward the treeline, where you will see a kiosk.

Prepare yourself before starting the trail, and you will have to first climb 300 feet of dominant shrubs and vines before going through rocky outcroppings and wetlands; at some point, you will find the boardwalks and bridges; once you are at the double-bough bridge, you are halfway through the hike.

Have fun with your friends while adventuring in the park. If you cannot go through the long trail route, use route seven trailheads. Exploring the Fountain Pond State Park is one of the fun things to do in Great Barrington.

Address: Us-7, Great Barrington, MA 01230

10. Berkshire Playwrights Lab

Berkshire Playwrights Lab
Credits: Serhii Bobyk / Shutterstock

Berkshire Playwrights Lab is the safe place for new playwrights to grow and nurture their passion for storytelling and writing. The playwrights focus on creating new play development and assisting established and emerging playwrights.

At the Berkshire Playwrights Lab, readings, workshops, and staged productions are hosted to relay Playwrights’ works to their audience, promoting the work Playwrights. If you love to watch stage plays or listen to stories written by the authors, then you should visit Berkshire Playwrights Lab.

Berkshire Playwrights Lab was established by three passionate Playwrights, Joe Cacaci, Jim Frangione, Bob Jaffe, and Matthew Penn, in 2007. The lab was established to encourage, develop and present new plays to the Berkshire community.

Address: 352 Main St Suite 202, Great Barrington, MA 01230-1814

11. W.E.B. DuBois Birthplace

W.E.B. DuBois Birthplace
Credits: Christ Revolution Church / Facebook
W.E.B. DuBois Birthplace

W.E.B. DuBois Birthplace is one of the top attractions in Great Barrington, and it is the birthplace and maternal home of the legendary poet W.E.B DuBois. It was established to engage the public in the life of W.E.B DuBois and its global significance and relevance to important issues of this current dispensation.

The W.E.B. DuBois Birthplace is a five-acre parcel in Great Barrington. The idea of a place to honor the life of W.E.B. DuBois was initiated by Professor Edmund W. Gordon and Walter Wilson in 1937. W.E.B. DuBois Birthplace was officially designated a National Historic landmark in 1979.

Take your family or friends to W.E.B. Dubois’s Birthplace to learn about W.E.B DuBois life and impact on the world. Visiting W.E.B. DuBois Birthplace is one of the top things to do in Great Barrington.

Address: Church Street, Great Barrington, MA 01230

12. Vault Gallery

Vault Gallery
Credits: Director of The Vault Gallery / Facebook
Vault Gallery

The Vault Gallery is a small art gallery located in an old bank building, the Mahaiwe Bank. The art gallery showcases the unique pieces of Marilyn Kalish; the architecture and facilities of the old bank also add to the exhibition at the gallery.

Marilyn Kalish is multimedia with eclectic creative pieces. Explore the Vault Gallery and check for your finest piece in the gallery. Her artworks are displayed in the gallery; Marilyn also has her workspace in the gallery. 

At the gallery, you will find beautiful contemporary artworks, the rooms of the gallery are well decorated and filled with beautiful pieces. While at the gallery, look out for the paintings showcasing women. Exploring Vault Gallery is one of the fun things to do in Great Barrington, MA, so do add to you list of places to visit in Great Barrington.

Address: 322 Main Street, Great Barrington, MA, Great Barrington, MA 01230-1859

13. The Emporium Antiques & Art Center

Emporium Antiques & Art Center
Credits: The Emporium Antiques & Art Center / Facebook
Emporium Antiques & Art Center

Do you love art? Are you fascinated by glass art? Then, it would help if you visited Emporium Antiques & Art Centre in Great Barrington, Massachusetts.

Emporium Antiques & Art Centre has the most extensive collection of Loetz glass in Massachusetts and beyond. Although you will find the most delicate glass art and collectibles at the antique store and art center, many pieces at the Centre are unique and are of museum quality.

There are many antique items like furniture, jewelry, accessories, ceramics, and many more. When you visit, you might be lucky to find a ceramic beer stein that is about 4-5feet high; you will also see butterflies in pictures frames hung on the walls of the art center.

A visit to Emporium Antiques & Art Center is one of the top things to do in Great Barrington.

Address: 319 Main St, Great Barrington, MA 01230-1608

14. Housatonic Flats Trail

Housatonic Flats Trail
Credits: antstang/ Shutterstock

Housatonic Flats is a short 0.9-mile-long loop trail in Great Barrington, perfect for new hikers and family hiking. This short loop trail leads to 26 acres of Housatonic Flats area in Great Barrington.

Housatonic Flats is a great place to enjoy wildlife watching while you hike on the plains in the woods. The Housatonic Flats are said to be a sacred and ancestral homeland of the Mohican people.

While hiking in the area, you may be lucky to spot a deer, fish in the river, otter, and many bird species lurking around. Have fun adventuring this trail and spotting animals and birds as you progress on the hike.

Wildlife watching or birdwatching is one of the best things at the Housatonic Flats in Great Barrington.

Address: Route 7, Great Barrington, MA 01230

15. Saint James Place

Saint James Place
Credits: Saint James Place / Facebook
Saint James Place

Saint James Place is one of the oldest structures in Great Barrington; the building was an Episcopal Church built-in 1857. The church building has been restored and preserved for cultural purposes with time.

Saint James Place is a cultural center and event space in Southern Berkshires, Great Barrington. It is known for hosting opera, historical talk, holiday market, etc. Saint James place has a serene environment with stunning architecture and interior.

Programs like special talks on the history of Berkshires and its people and other outstanding theatrical performances to keep you entertained are held at Saint James Place; this attracts locals and visitors from different places to the cultural Centre.

Saint James Place was established in 2017, and since its inception, over 40 groups have utilized the building for different purposes, such as stage for performance, office space, and rehearsal ground. Watch dance performances, theatrical plays, music, and other exciting things when visiting here.

Address: 352 Main St, Great Barrington, MA 01230-187

For a fun time in Massachusetts, take to exploring our list of things to do in Rogers, and fun things to do in Falmouth for a fun vacation time.

16. Asia Barong Gallery

Asia Barong Gallery
Credits: AsiaBarong Gallery / Facebook
Asia Barong Gallery

Asia Barong Gallery is a unique museum where you can wander through and learn about the world’s cultures using high-quality ethnographic art and other exciting types of art. Teach your children about the continent and different people of the world at Asia Barong Gallery.

These ethnographic art are unique and rare, the artworks in the gallery are gotten from artisan families in developing countries and are brought to the west to be sold, and the money will be reimbursed back to the artisan families

Asia Barong serves as a middle man between artisan families in Asia and buyers in the west. The Asia Barong Gallery aims to help and support local artisans in Asia by exhibiting their works in the west. Explore these beautiful artworks when you visit Great Barrington.

This answers what to do in Great Barrington, for a fun time, makes one of the best places to visit in Great Barrington, MA

Address: 199 Stockbridge Rd, Great Barrington, MA 01230-1227

17. Yellow House Books

Yellow House Books
Credits: jakkaje879/ Shutterstock

Read books or purchase a book for your family or friends at the Yellow House Books in Great Barrington, Massachusetts.

Yellow House Books is three rooms book store cum library that offers a wide selection of used and rare books in Greater Barrington. The books are well stacked according to their genre and type.

At Yellow House Books, you will find books on music, arts, photography, DIY, and inspiration. There are also lovely children’s books for different ages and adult self-help books. Other books you will find at the book house are mythology, metaphysical, religion, philosophy, and many more.

Look around the book house for incredible collectibles, and if you love music, there is a variety of musical sheets at the Yellow Houses Books.

Address: 252 Main St, Great Barrington, MA 01230-1779

18. The Well Restaurant + Bar

Well Restaurant + Bar
Credits: The Well Restaurant + Bar / Facebook
The Well Restaurant + Bar

Having dinner at the Well Restaurant is one of the best things to do in Great Barrington.

The Well Restaurant is a beautiful restaurant with a great variety of food. Check out their menu and try out the delicious specials when visiting the restaurant.

When you visit the restaurant, you can either stay in the outdoor area or the indoor location. Enjoy the relaxed environment while having a delicious meal with your family or friends at the Well Restaurant. The restaurant has an indoor and outdoor setting,

The Well Restaurant opens from Wednesday to Saturday from 4 pm to 8 pm, and it is a perfect place for a dinner date with your loved ones. You can also order takeout if you do not want to stay at the restaurant.

19. Jameson Limited Reserve

Jameson Limited Reserve
Credits: Ruslan Semichev / Shutterstock

Jameson Limited Reserve manufactures rare whiskey in hand-selected oak casks in Europe and America. This exceptional whiskey has a rich mixed taste of vanilla, wood, spice, and toffee, and this unique taste is due to the particular process used to manufacture these wines.

Jameson Limited Reserve alcoholic beverages are top-notch and have won awards, one of which is Angel’s Envy Kentucky Straight Bourbon. Each batch of the handcrafted bourbon is well conditioned, blended, and processed. 

Enjoy the taste of unique rich, and smooth whiskey when you visit the Jameson Limited Reserve. A visit to the whiskey reserve is one of the top things to do in Great Barrington.

Address: 312 Main St, Great Barrington, MA 01230-1742

20. Bernay Fine Art

Bernay Fine Art
Credits: Bernay Fine Art / Facebook
Bernay Fine Art

Bernay fine art is a contemporary art gallery in Great Barrington filled with contemporary arts in various art forms such as painting, glass, sculpture, ceramics, and many more. The art gallery also organizes art shows and exhibitions for locals and visitors.

At Bernay fine art, you will find artworks from artists from all over the world; works by local artists in Berkshire are displayed in the gallery.

Take your family or friends with you as you explore Bernay’s fine art gallery visiting Great Barrington. Bernay Fine Art was established in 2019 to represent the unique art pieces of distinguished artists working in various media.

Address: 296 Main St Suite #1, Great Barrington, MA 01230-1607

21. Guido’s Fresh Marketplace

Guido's Fresh Marketplace
Credits: Aleksandar Mijatovic / Shutterstock

Guido’s Fresh Marketplace is your one-stop store for your new food need. Stop at Guido’s Fresh Marketplace to shop for your vegetables, fruits, flowers, meat, seafood, fresh farm produce, and many more items when you visit Great Barrington.

Guido’s Fresh Marketplace is a family-owned business run and managed by the family. You will also find freshly prepared foods ready for your consumption at the independent marketplace. Take your family or friends to the market for an exciting day of foodstuff shopping in the market.

The marketplace is a beautiful place to buy your foodstuffs; the staff is friendly and willing to assist you while purchasing your food items. Shopping for food items at Guido’s Fresh Marketplace is one of the fun things to do in Great Barrington, MA.

Address: 760 South Main Street, Great Barrington, MA 01230-2014

22. Charter The Berkshires

Charter The Berkshires
Credits: 5m3photos / Shutterstock

The Charter The Berkshires is a fishing guide service that provides fishing trips and incredible outdoor experiences in Berkshire. The charter ride goes through the Berkshire Mountains of western Massachusetts.

Enjoy fishing through many lakes, streams, and rivers while you tour the area. If you do not wish to fish, you can watch the waters and enjoy the beauty of nature. Go on customized or solo trips with your family and friends using Charter The Berkshires to get the most from the short adventure.

Charter The Berkshires runs all year round as there is always something to enjoy while on the fishing trip. Going on fishing trips with Charter The Berkshires is one of the fun things to do in Great Barrington, MA.

23. Lauren Clark Fine Art

Lauren Clark Fine Art
Credits: Lauren Clark Fine Art / Facebook
Lauren Clark Fine Art

Lauren Clark Fine Art is another amazing contemporary art gallery in Great Barrington; at Lauren Clark Fine Art, there are artworks from over 40 local and internationally recognized artists.

When you explore the beautiful art gallery with your friends and family, you will find artworks like paintings, sculptures (indoor and outdoor), fine art prints, photographs, jewelry, ceramics, etc.

Browsing through the artworks in Lauren Clark Fine Art is one of the best things to do in Great Barrington, MA. The fine art gallery also has a community of artists where local artists can share experiences and artwork inspirations.

At Lauren Clark Fine Art, you can bring your photographs for professional framing. These framings are done by artists and with unique materials that last a long time. The fine art gallery has done framing for pictures and other artworks for about 30 years.

Take your friends and family to this unique contemporary art gallery for an evening of art and relaxation. 

Address: 684 Main St, Great Barrington, MA 01230-2156

Massachusetts holds quite some fun attractions and activities, explore some of its fun cities, here are guides on Fall River , Lenox, and Springfield.

Start planning your trip to Great Barrington

Great Barrington is an amazing city with many excellent activities to enjoy. W.E.B DuBois Birthplace and Mahaiwe Performing Arts Centre are top international attractions and a must-visit in Great Barrington.

Explore the peaceful town while visiting the museums, art galleries, historical sites, parks, restaurants, forest trails, hotels, etc.

Also visit Fountain Pond Park, Monument Mountain, Taft Farm, Lake Mansfield, Ski Butternut, Emporium Antiques and Art Centre, Vault Gallery, and many more exciting places to enjoy the beautiful town.

Have a fun trip!