Boston Magazine recently rated Great Barrington, MA, as one of the best places to live in the state for many reasons, including the area’s outdoor activities, scenic surroundings, and clean air.

The settlement was initially inhabited in 1726, and from 1742 to 1761, it served as Sheffield’s north parish.

Great Barrington, MA, was given official incorporation status in 1761, taking its name from the Gloucestershire, England, settlement of the same name.

There is a lot to do in this city. If you’re considering visiting this city, you’ll want a knowledgeable guide to help you fully experience the place.

Planning a trip to this city? This article explores some of the interesting and awesome locations in this city. Let’s check them out.

Things to Do in Great Barrington, MA

1. Fountain Pond State Park

At the Berkshire South Regional Community Centre lies the enjoyable Fountain Pond State Park, which has a pine forest, stone stairs, boardwalks and bridges, pathways, and a variety of vegetation, including mushrooms and wildflowers.

Before using the ropes course or any other park amenities, notify the Berkshire South Regional Community that you will be at the park. Follow the trailhead into the treeline, where you will see a kiosk, to locate the stone stairs.

Prepare yourself before beginning the trek since you will first have to climb 300 feet of heavy plants and vines before passing through rocky outcroppings and marshes. Once you reach the double-bough bridge, the trip is halfway complete.

Adventure at the park with your buddies and have fun. If you can’t take the long trail path, use the trailheads along Route 7. One of the enjoyable things to do in Great Barrington, MA, is to explore Fountain Pond, State Park.

Location: Us-7, Great Barrington, MA 01230

2. Berkshire Playwrights Lab

New playwrights may develop and nourish their love of storytelling and writing in a secure environment at Berkshire Playwrights Lab.

The writers concentrate on developing new plays and helping seasoned and up-and-coming playwrights.

Readings, workshops, and staged performances are held at the Berkshire Playwrights Lab to present playwrights’ works to their audience and promote playwrights’ work.

Visit Berkshire Playwrights Lab if you enjoy reading or listening to stories created by authors or watching theatrical plays.

Three ardent playwrights, Joe Cacace, Jim Frangione, Bob Jaffe, and Matthew Penn, founded the Berkshire Playwrights Lab in 2007.

The lab started encouraging, producing, and introducing new plays to the Berkshire area.

Location: 352 Main St, Suite 202, Great Barrington

3. W.E.B DuBois Birthplace

The famed poet W.E.B. DuBois was born and raised in Great Barrington, where his birthplace is one of the city’s main tourist destinations.

It was created to educate the public about W.E.B. DuBois’ life, its significance worldwide, and how it relates to crucial concerns facing this period.

Professor Edmund W. Gordon and Walter Wilson came up with the concept of a memorial to W.E.B. DuBois in 1937.

The birthplace of W.E.B. DuBois was formally recognized as a National Historic Landmark in 1979.

Visit W.E.B. Dubois’s birthplace with your family or friends to learn about his life and global contributions.

In Great Barrington, MA, one of the best things to do is to visit the birthplace of W.E.B. DuBois.

Location: Church Street, Great Barrington, MA 01230

4. Vault Gallery

A modest art gallery called The Vault Gallery is housed in the Mahaiwe Bank, a former bank. The art gallery exhibits the one-of-a-kind works of Marilyn Kalish; the former bank’s amenities and architecture further enhance the presentation there.

Multimedia artist Marilyn Kalish is known for her many creative works. Search the Vault Gallery for your best work there while you explore. In addition to having a workplace, Marilyn has her artwork on show in the gallery.

Beautiful modern artwork can be seen at the gallery, and the rooms are well-furnished and full of lovely items. Keep an eye out for the paintings of ladies while you’re in the gallery.

Add exploring Vault Gallery to your list of things to do in Great Barrington, MA, since it is one of the city’s most enjoyable attractions.

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

5. Emporium Antiques And Art Center

Love the arts? Are works of glass art your thing? Going to the Emporium Antiques & Art Centre in Great Barrington, MA might be beneficial.

The most extensive collection of Loetz glass in Massachusetts and worldwide is found at the Loetz Glass Museum.

The antique shop and art center are where you will discover the most delicate glass art and treasures, but many of the items there are one-of-a-kind and of museum caliber.

Many vintage things, including pottery, jewelry, accessories, and furniture. If you’re lucky, you might locate a porcelain beer stein roughly 4-5 feet high during your visit.

The art center also has photo frames with butterflies hanging on the walls.

One of the best things to do in Great Barrington, MA, is to go to the Emporium Antiques & Art Center.

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

6. Housatonic Flats

A 0.9-mile circular route in Great Barrington called Housatonic Flats is ideal for families and novice hikers. Twenty-six acres of the Housatonic Flats region in Great Barrington are accessible through this brief circle walk.

You may go on a trek through the wooded plains of Housatonic Flats and take in the wildlife. The Mohican people claim to have a heavenly homeland on the Housatonic Flats.

You could be fortunate to see a deer, fish in the river, an otter, and various birds when trekking in the region. As you go along, enjoy exploring the trail and looking for wildlife.

Wildlife or bird watching is one of the most acceptable activities at the Housatonic Flats in Great Barrington, MA.

Location: Route 7, Great Barrington, MA 01230

7. Saint James Place

One of Great Barrington’s first buildings in Saint James Place was constructed as an Episcopal church in 1857. With time, the church tower has been repaired and kept for cultural reasons.

Saint James Place is a cultural hub and gathering place in Great Barrington, MA, and the Berkshires.

Opera, historical lectures, a holiday market, etc., are all held there. Saint James Place boasts beautiful interior and exterior architecture.

Saint James Place hosts events that draw residents and tourists from other locations, such as unique presentations on the history of the Berkshires and its inhabitants and top-notch theater productions.

Over 40 organizations have used Saint James Place since it opened in 2017 for various uses, including a performance stage, office space, and a practice area.

You may see dancing performances, plays on stage, concerts, and other fascinating events when you come here.

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

8. Asia Barong Gallery

The Asia Barong Gallery is a singular museum where visitors may stroll around and discover the cultures of the globe via excellent ethnographic art and other fascinating forms of art.

You may instruct your kids at the Asia Barong Gallery about the continent and many global cultures.

The artworks at the gallery were acquired from artisan families in developing countries and transported to the west to be sold.

The proceeds from the sales will be sent back to the artisan families whose works are distinctive and unusual.

Asia Barong acts as a go-between for western consumers and Asian artisan families. By displaying their creations in the west, the Asia Barong Gallery seeks to assist and sustain regional artists in Asia. Visit Great Barrington and have a look at these lovely pieces of art.

This constitutes one of the greatest sites to visit in Great Barrington, Massachusetts, since it provides ideas for entertaining things to do there.

Location: 199 Stockbridge Rd, Great Barrington

9. Yellow House Books

You may read or buy books for your loved ones at Yellow House Books in Great Barrington, MA.

In Greater Barrington, Yellow House Books is a three-room bookshop/library that provides an extensive range of secondhand and unusual books. The books are neatly placed by their kind and genre.

You may get books about music, the arts, photography, DIY, and inspiration at Yellow House Books. There are also excellent books for children of all ages and self-help books for adults.

The bookstore also has a wide selection of books on mythology, metaphysics, religion, philosophy, and much more.

Look through the bookstore for unique souvenirs, and if you enjoy music, Yellow Houses Books has a wide selection of musical notations.

Location: 252 Main St, Great Barrington

10. Guido’s Fresh Marketplace

Your one-stop shop for all your new food needs is Guido’s Fresh Marketplace. Stop at Guido’s Fresh Marketplace when visiting Great Barrington to get fresh farm produce, meat, flowers, veggies, fruits, and more.

A family-owned company, Guido’s Fresh Marketplace is controlled and managed by the family. At the independent market, you may also buy freshly cooked food.

Bring your family or friends to the need for a fun day of food shopping.

The market is a lovely place to buy food, and the employees are helpful and courteous. One of the enjoyable things to do in Great Barrington, MA, is grocery shopping at Guido’s Fresh Marketplace.

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

11. Charter The Berkshires

A charter Fishing tour and unique outdoor experiences are offered by The Berkshires, a guiding fishing service in Berkshire. Western Massachusetts’ Berkshire Mountains are traversed during the charter flight.

While touring the region, take advantage of fishing in the various lakes, streams, and rivers. If fishing is not your thing, you may still observe the waterways and take in the splendor of nature.

Take individualized or solo tours with your family and friends using Charter The Berkshires to make the most of the brief excursion.

Because there is always something to do while fishing, Charter The Berkshires operates all year long.

One of the entertaining things to do in Great Barrington, Massachusetts, is fishing with Charter The Berkshires.

Location: 119 Park St, Great Barrington, MA 01230.

12. Lauren Clark Fine Art

Another fantastic modern art gallery in Great Barrington is Lauren Clark Fine Art, which features works by more than 40 nationally and globally renowned local and international artists.

You may find artworks like paintings, sculptures (both indoor and outdoor), fine art prints, photography, jewelry, pottery, etc.

One of the most incredible things to do in Great Barrington, MA, is to look through Lauren Clark’s fine art artwork.

The fine art gallery also hosts an artist community where nearby artists may exchange insights and sources of inspiration.

You may bring your photos to Lauren Clark Fine Art for expert framing. These framings are created by artisans using unique, long-lasting materials.

Since roughly 30 years ago, the fine art gallery has been framing photographs and other artwork.

Bring your loved ones and friends to this special modern art exhibition for a restful evening.

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

13. Monument Mountain

One of Great Barrington’s leading tourist destinations, Monument Mountain, has drawn tourists and hikers worldwide.

The mountain’s elevation is 1,642 feet, and its peak offers a breathtaking perspective of the Housatonic River Valley’s picturesque surroundings.

Monument Mountain inspired many famous authors of the 19th century; novels, poetry, and other literary works were written about it. Even painters and other artists used the mountain as an inspiration for their work.

Herman Melville’s novel Moby-Dick, motivated by a picnic trip on the hill with Nathaniel Hawthorne in 1850, is one literary work influenced by the mountain. Later, Nathaniel Hawthorne received a dedication to the work.

One of the most delicate things to do in Great Barrington is hiking on Monument Mountain.

Location: Route 7, Great Barrington, MA 01230

14. Ski Butternut

Ski Butternut in Great Barrington and have fun skiing there with your loved ones. This is among the enjoyable activities in Great Barrington, MA.

When visiting Great Barrington in the winter, Ski Butternut is a lovely destination to go skiing with your friends or family, enjoy the snow, and go on a fantastic journey. Ski Butternut provides distinct and enjoyable snow zones depending on your ability level.

There is a separate ski area for the enjoyment of both novices and specialists. One-fifth of Ski Butternut’s 110 acres of skiing terrain is appropriate for beginners. Each person may find something to love at Ski Butternut.

For the convenience of visitors, Ski Butternut also provides 11 lifts and lessons for novices. So when you visit Great Barrington in the winter, take your friends and family to Ski Butternut.

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

15. Guthrie Center And Foundation

The Guthrie Centre & Foundation is a hub for cultural preservation, facilitating academic success, and encouraging community engagement to fulfill the continuous needs of the community.

The Guthrie Centre & Foundation is well known for its ecumenical worship services and artistic and musical cross-cultural cooperation.

Arlo Guthrie established the Centre, but in 1991 it was given his parents’ names, Woody & Marjorie Guthrie, as a tribute.

The Guthrie Centre & Foundation is a place of contemplation since it is the site of a significant historical event.

Beyond places of worship and cultural promotion, the Guthrie Centre & Foundation is also a venue to eat and take in performances at the Old Trinity Church.

So bring your friends here to enjoy learning, socializing, and having fun.

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

16. Mahaiwe Performing Arts Center

Great Barrington’s Mahaiwe Performing Arts Center is a launching pad for theater productions. The Center wants to offer the Berkshires and nearby areas year-round family, educational, performing arts, and cinematic programming.

Enjoy excellent performances by very skilled artists in dance, music, theater, and opera at Mahaiwe Performing Arts Center.

Keep track of your most nuanced performances as you observe and interact with the crowd.

Add seeing a play at the Mahaiwe Performing Arts Center with your friends or family to your bucket list of things to do in Great Barrington, MA.

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

17. Taft Farms

In Great Barrington, MA, explore Taft Farms to learn more about farming and to try it with your loved ones.

Small family-run Taft Farm has provided agricultural services to the Berkshire region for over 50 years.

The farm’s proprietors take good care of it and keep it tidy. Take a stroll around the lovely green farm and discover its other exciting features.

You may purchase fresh farm food and learn how to run the farm when you visit Taft Farm. Since its founding in 1961, Taft Farm has continually practiced sustainable farming and abundant harvest.

One of the most delicate things to do in Great Barrington is to visit Taft Farm, so make sure you do it when you are there.

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

18. Lake Mainfield

A 29-acre leisure area called Lake Mansfield has a forest and a pond. Lake Mansfield is an excellent place to unwind and spend some time in nature.

Enjoy a picnic with friends or family close to the lake’s shore. You may sit and take in the scenery while you and your sweetheart stroll around the woodland pathways. Another fantastic thing to do around Lake Mansfield is a hike.

Put on your hiking gear and head out with your hiking buddy to explore the lovely green forest on the 0.25-mile route you’ll discover at Lake Mansfield.

One of the enjoyable things to do in Great Barrington, MA, is hiking around Lake Mansfield.

19. Housatonic River Walk

The Housatonic River Walk should not be missed among the many paths in Great Barrington. Among the best things to do in Great Barrington is to stroll along the Housatonic River Walk.

The Housatonic River Walk is a greenway route traverses Great Barrington’s downtown by following the west bank of the Housatonic River.

The path is the ideal location for getting some fresh air workout. You can go for a solo or group stroll, run, or jog around the area.

The Housatonic River region is clean and tranquil due to the town of Great Barrington’s diligent efforts to preserve and restore its beauty. The Housatonic River Walk is a beautiful area to find peace.

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

20. Windy Hill Farm

Have you ever visited a horticulture place with many different fruits, flowers, and plants? If not, you ought to visit Great Barrington’s Windy Hill Farm.

Windy Hill Farm has provided services to Berkshire County and other Massachusetts Counties, a horticulture company with various plants.

At the Windy Hill farm, there is an apple orchard, a retail garden center, a blueberry field, a specialist decorative nursery stock cultivated in the area, etc.

Over its more than 28 years of operation, the diverse horticultural farm has provided services for a wide range of species, including specimen and flowering trees, tree fruits and small fruits, ornamental shrubs and grasses, conifers and broadleaf evergreens, vines, hardy shrub roses, and many more.

Visit Windy Hill Farm for a fantastic day of picking fruits and learning about tiny fruit design, design and installation, and home orchards; you will also find native species and classic favorites.

One of the enjoyable activities in Great Barrington is picking or plucking fruit at the Windy Hill Farm. Visit Windy Hill Farm with friends and family and enjoy a fantastic horticulture experience.

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

21. Well Restaurant

One of the most incredible things to do in Great Barrington is to eat at the Well Restaurant.

Beautiful restaurant The Well Restaurant offers a wide selection of cuisine. When you visit the restaurant, look through the menu and sample some delicious specials.

You can choose to stay in the restaurant’s indoor or outdoor spaces when you go there. Enjoy a great dinner at the Well Restaurant with your family or friends in a tranquil setting. There are indoor and outdoor seating areas at the restaurant.

The Well Restaurant, open from Wednesday through Saturday from 4 pm to 8 pm, is the ideal location for a romantic supper with your loved ones. If you don’t want to eat there, you can instead order takeaway.

Location: 312 Main St, Great Barrington, MA 01230, United States

22. Jameson Limited Reserve

Jameson Limited Reserve produces rare whiskey in hand-selected oak barrels in Europe and America.

This unique whiskey has a complex flavor profile with notes of vanilla, oak, spice, and toffee. This distinctive flavor results from the unusual method employed to create these wines.

Alcoholic drinks from Jameson Limited Reserve are of the highest quality and have garnered recognition, including Angel’s Envy Kentucky Straight Bourbon.

Each batch of hand-crafted bourbon is adequately mixed, processed, and conditioned.

When you visit the Jameson Limited Reserve, savor the flavor of the distinctive, rich, and smooth whiskey. One of the best things to do in Great Barrington is to visit the whiskey reserve.

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

Conclusion

This city has excellent adventures awaiting you. You’ll have a wonderful time in this city regardless of your age.

Whether traveling alone or with friends and family, do well by exploring the city’s best locations and attractions.

Use this article as your friendly guide to exploring some of the interesting things that this city offers.