Great Barrington

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

Wondering what to do on getting to Great Barrington, MA?

This article promises to be expository and informative as I will be discussing with you the 23 best and most fun things you can do in the city.

You can locate Great Barrington in Berkshire County, Massachusetts, United States. 

The city is best described as a small but peaceful town featuring several galleries, historical sites, as well as natural habitats, and these features are what attract numerous visitors from across the world.

Below are the top best and most fun things you can do while you are in Great Barrington.

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

1. Monument Mountain

Over the years, Monument Mountain has been one of the top attractions in Great Barrington attracting tourists, most especially hikers from all over the world.

Also, this mountain has an elevation of 1,642 feet and provides an incredible view of the alluring landscape of Housatonic River Valley from the mountain summit.

Aside from going there for a hike, Monument Mountain served as an inspiration for various literary giants such that poems, books, and other literary works were written referring to Monument Mountain. 

Address: Route 7, Great Barrington, MA 01230

2. Ski Butternut

At Ski Butternut, you can go with your family and friends to enjoy skiing, experience a beautiful adventure during winter, and have fun in the snow.

Interestingly, they have a different ski area for beginners and another area where professionals can go have fun. 

In addition to this, Ski Butternut offers classes for beginners and 11 lifts for tourist comfort. 

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

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3. The Guthrie Centre & Foundation

Guthrie Centre & Foundation is best described as a center known for fostering educational achievement, cultural preservation, and facilitating community outreach to meet the present needs of the community. 

That being said, this place hosts a historical event thereby making the center an important place where you can reflect.

Another thing that happens at  Guthrie Centre & Foundation is the performances at the Old Trinity Church which is where the Guthrie Centre & Foundation is located. 

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

4. Mahaiwe Performing Arts Centre

Mahaiwe Performing Arts Centre is known to house a wide range of theatrical performances in Great Barrington. 

It aims at presenting the film, educational, performing arts, and family programs throughout the year for the Berkshires as well as other bordering communities.

You will surely be entertained upon visiting Mahaiwe Performing Arts Centre by watching incredible performances of very skilled performers via theatre, dance, music, and opera. 

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

5. Taft Farms

Taft Farms is where you can learn and explore farming with your loved ones in Great Barrington, Massachusetts because it has been in existence for more than 50 years.

Expect to learn how to run their farm and also shop for fresh farm produce, and this farm is known for having a consistent bountiful harvest.

As an Agricultural enthusiast, endeavor to visit Taft Farm when you arrive in Great Barrington.

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

6. Lake Mansfield

Being a 29-acres recreational area, Lake Mansfield features a pond and forest. 

You can choose to take a walk and stroll through the forest paths with your friends, or you can sit and relish the beauty of the site. 

Also, you will find a 0.25-mile trail within the forest area thereby making an ideal spot for hiking, therefore, exploring the beautiful green forest when hiking at Lake Mansfield.

7. Housatonic River Walk

Among numerous trails in Great Barrington, the Housatonic River Walk is one of the best trails in Great Barrington. 

In case you are looking for an ideal place to participate in outdoor exercise, visit the trail where you can run, walk, or jog around the neighborhood.

I must state that the Great Barrington community has tried in the aspect of striving to protect and maintain the beauty of the Housatonic River area, and that is why you will find the area calm and neat.

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

8. Windy Hill Farm

If you have ever fantasized about being in a horticultural site having numerous flowers, fruits, and other plants, then a visit to the Windy Hill Farm in Great Barrington is a place to be.

It may interest you to know that this farm has been in existence for more than 28 years.

At Windy Hill Farm, you will find a retail garden center, an apple orchard, field-grown specialty ornamental nursery stock, a blueberry field, and so on.

Also, there are varieties of the specimen and flowering trees; hardy shrub roses, ornamental shrubs and grasses; conifers and broadleaf evergreens; tree fruits and small fruits; vines; and so many more.

You are allowed to pick and pluck fruits, and that makes it an intriguing thing to do in Great Barrington. 

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

9. Fountain Pond State Park

The Fountain Pond State Park is situated at Berkshire South Regional Community Centre featuring stone steps, a pine forest, trails, boardwalks and bridges, and various plants like mushrooms and wildflowers.

Ensure that you let the Berkshire South Regional Community know before using the rope course or any other equipment in the park. 

There is a long trail route present there, and if you can’t go through the long trail route, make use of the route seven trailheads. 

Address: Us-7, Great Barrington, MA 01230

10. Berkshire Playwrights Lab

It is safe to describe Berkshire Playwrights Lab as a convenient place where new playwrights can develop and nurture their passion for storytelling and writing. 

Furthermore, the essence of establishing the playwrights is to concentrate on creating new play development, encouraging both renowned and emerging playwrights.

Also, note that at the Berkshire Playwrights Lab, workshops, readings, and staged productions are hosted to present Playwrights’ works to their audience thereby fostering the work of Playwrights. 

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

11. W.E.B. DuBois Birthplace

W.E.B. DuBois Birthplace as the name implies is the birthplace and maternal home of the famous poet W.E.B DuBois, and it is known to be one of the major attractions in Great Barrington. 

The aim of establishing this place is to honor and educate the public about the life of W.E.B DuBois, the role he played globally, and its relevance to significant issues of this present dispensation.

Remember to take your family or friends along with you to W.E.B. Dubois’s Birthplace to have a sound knowledge of W.E.B Dubois’s life and the impact he made in the world. 

Address: Church Street, Great Barrington, MA 01230

12. Vault Gallery

Situated in an ancient bank building, the Mahaiwe Bank,  the Vault Gallery is an art gallery that displays the impressive pieces of Marilyn Kalish.

It is in this gallery that you can explore the Vault Gallery and look out for Marilyn’s finest piece in the gallery. 

In addition to this, there are attractive modern artworks in the gallery, and the rooms there are well decorated and filled with beautiful pieces.

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

13. The Emporium Antiques & Art Center

Are you an art lover who is interested in glass art? If yes, a visit to Emporium Antiques & Art Centre in Great Barrington, Massachusetts will be a great idea.

This art center features the most comprehensive collection of Loetz glass in Massachusetts and beyond. 

In addition to this, you will see the most delicate glass art and collectibles at the Emporium Antiques & Art Centre as well as various unique pieces that meet the standards of the museum.

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

14. Housatonic Flats Trail

This is a short 0.9-mile-long loop trail in Great Barrington very suitable for fresh hikers and of course, professionals. 

While hiking on the plains in the woods, you will be opportune to have an amazing time watching wildlife, maybe you may see a deer, various bird species, and even fish in the river.

It is rumored that the Housatonic Flats is a sacred and ancestral homeland of the Mohican people.

Address: Route 7, Great Barrington, MA 01230

15. Saint James Place

Constructed in the year 1857, Saint James Place is one of the most ancient structures in Great Barrington, and this building has been preserved over the years for cultural purposes.

This place is known to be a cultural center and event space in Southern Berkshires, Great Barrington, and it serves as a host for historical talk, opera, holiday market, and so on.

Since its establishment in 2017, Saint James Place has hosted more than 40 groups who used the building for different purposes like office space, a stage for performance, and rehearsal ground. 

That being said, you can visit here to feed your eyes with theatrical plays,  music, dance performances, as well as other intriguing things when you visit here.

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

16. Asia Barong Gallery

If you are still in search of a fun thing to do in Great Barrington, MA, a visit to Asia Barong Gallery will answer your question as you will be given the opportunity to move around and use high-quality ethnographic art and other types of art to learn about the world’s cultures. 

One word to use in describing the artworks found there is unique, and they are obtained from artisan families in developing countries and sold in the west, and the proceeds from the sales will be given back to the artisan families

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

17. Yellow House Books

If you want to travel the world through books, you should either read or buy at the Yellow House Books in Great Barrington, Massachusetts.

This place is best described as a three rooms book store offering a wide range of used and unique books in Greater Barrington, find them arranged according to their genre and type.

You are sure to lay your hands on music, arts, photography, DIY, and inspiration at Yellow House Books, and there are interesting books for both kids and adults alike.

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

18. The Well Restaurant + Bar

For an incredible dining experience, you should head to the Well Restaurant as it is one of the best things you can do in Great Barrington.

This restaurant has both an indoor and outdoor area where you can relax while enjoying a tasty meal.

You will find the Well Restaurant open from Wednesday to Saturday from 4 pm to 8 pm, and I recommend this location for a dinner date with your loved ones. 

19. Jameson Limited Reserve

Jameson Limited Reserve is the manufacturer of unique whiskey in hand-picked oak casks in Europe and America. 

If you taste this whiskey, you will notice that it has a rich combined taste of wood, vanilla, spice, and toffee, and this taste is a result of the process used in manufacturing these wines.

It’s okay to refer to Jameson Limited Reserve alcoholic beverages as an award-winning reserve, and one of the beverages that earned them this is Angel’s Envy Kentucky Straight Bourbon. 

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

20. Bernay Fine Art

Bernay fine art is described as a modern art gallery in Great Barrington that is filled with modern arts in different art forms like sculpture, painting, glass, ceramics, and lots more. 

In addition to this, the art gallery conducts art shows and displays for locals and visitors.

Here you will find unique art pieces of well-known artists working in different media.

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

21. Guido’s Fresh Marketplace

If you have any need to buy food, then, you should head to Guido’s Fresh Marketplace, and that is where you can shop for your flowers, meat, vegetables, fresh farm produce, fruits, seafood, and many other items when you visit Great Barrington.

Furthermore, you will be served freshly prepared foods, so, feel free to take your family or friends to this place.

That being said, for all your foodstuff needs, you should visit Guido’s Fresh Marketplace, and the staff is sociable and ready to help you while buying your food items. 

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

22. Charter The Berkshires

The Charter The Berkshires is defined as a fishing guide service that provides fishing tours and outstanding outdoor experiences in Berkshire. 

During the trip, you will fish through several streams, lakes, and rivers while touring the area. 

You can also watch the waters and enjoy the attractiveness of nature, you can go on personal trips with your family and friends.

23. Lauren Clark Fine Art

Lauren Clark Fine Art made it to our list of fun things to do in Great Barrington because it’s considered to be an outstanding contemporary gallery featuring more than 40 local and internationally recognized artists.

Some of the artworks you will see when exploring the stunning art gallery include sculptures (indoor and outdoor), jewelry, paintings, photographs, fine art prints, ceramics, etc.

In addition to this, you can bring your photographs so that they can be framed for you at Lauren Clark Fine Art by artists and with unique materials that are long-lasting. 

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


Barrington, MA is an interesting vacation destination anyone can visit to have an incredibly fun time.

As you can see, there is a wide range of fun activities and amenities that will interest you in this city.

All you need to do is to pick one or two of them and enjoy yourself during your stay in Great Barrington, MA.

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