Things to Do in the Berkshires

There is something magical about the Berkshires. Surrounded by breathtaking mountain vistas, this is an area full of history, culture, and the great outdoors just waiting to be explored. History buffs can spend days visiting historic homes, sites, and museums. World-class music, theater, and dance are found on many stages throughout the area all year round and make up some of the best Berkshire activities in the area. Outdoor enthusiasts will find miles and miles of trails for hiking and biking, rivers and lakes to explore and slopes for skiing in winter.

For a list of our favorite things to do in the Berkshires for your visit, be sure to download a free copy of our Berkshires Travel Guide!

Video courtesy of the Berkshire Visitor’s Bureau

Hungry visitors will find a multitude of outstanding restaurants offering great food made from locally grown ingredients. Wondering what to do in the Berkshires? Be sure to look over our list of the best Berkshire attractions, activities, and things to do in the Berkshires. Whether you want to relax in this beautiful mountain area of the Berkshires or find adventure, there’s something for everyone.

Close to our Berkshires bed and breakfast visitors will find the oldest covered bridge in Massachusetts, two wildlife preserves with lovely trails to hike, and even a ukulele factory to visit. As for other unique Berkshire activities, there is also a wonderful array of antique stores to poke about in and find a treasure or two. Other Berkshire attractions are just a short drive away.

The Best Berkshire Activities & Attractions

Music & Dance in the Berkshires

1. Tanglewood

Tanglewood Music CenterTanglewood is the idyllic Berkshire summer home of the Boston Symphony Orchestra. It is one of most popular Berkshire activities. June through Labor Day, the Tanglewood music festival offers classical, jazz and popular concerts daily in Lenox.

2. Jacob’s Pillow Dance Festival

For over 70 years, the Jacob’s Pillow Dance Festival has been considered one of the premier dance venues in the world. Time Magazine calls the festival, “the hub and mecca of dancing in North America.” The Jacob’s Pillow Dance Festival offers over 300 free and ticketed performances each summer in Beckett, MA.

Art in the Berkshires

3. Norman Rockwell Museum

The Norman Rockwell Museum in Stockbridge features the largest collection of original Norman Rockwell art. The museum also features changing exhibitions of other illustrators and the painter’s studio.

4. Clark Art Institute

This is an art museum and research center in Williamstown. Exhibits at the Clark Art Institute focus on French impressionist, Old Master, and American paintings, with excellent special exhibitions.

5. MASS MoCA

This is the country’s largest contemporary art center. MASS MoCA features a vast array of performances and exhibitions housed on a 19th-century factory campus in North Adams.

Breweries in the Berkshires

Try a Flight at the Big Elm Brewery6. The Big Elm Brewery

Get a tour and tasting at the Big Elm Brewery in Sheffield from noon to 4 pm on Saturdays.

7. Berkshire Mountain Distillery

Established in 2007, Berkshire Mountain Distillers (BMD) has created a line of award-winning artisanal spirits including Greylock Gin, Ethereal Gins, Ragged Mountain Rum, Ice Glen Vodka, Berkshire Bourbon and New England Corn Whiskey. Tours start every hour on Friday and Saturday. Located in Sheffield.

Theater in the Berkshires

8. Berkshire Theatre Group

Live music, comedy, dance, family shows and more at the Unicorn, Colonial, and Fitzpatrick Theatres (all part of the Berkshire Theatre Group) in Pittsfield and Stockbridge.

9. Mahaiwe Theatre

Come See Dances at the Mahaiwe TheaterYear-round arts center in the Mahaiwe Theatre, a restored historic theater presenting live music, theater, dance and family programs as well as classic films.

10. Shakespeare & Company

The best of Shakespeare and new plays, free family shows; Shakespeare & Company performs all summer, fall, and winter.

11. Barrington Stage Company

The Barrington Stage Company is an award-winning theater on three stages in Pittsfield.

History of the Berkshires

12. Sheffield Historical Society

A group of local residents organized the Sheffield Historical Society in 1972 to preserve the story of the oldest town in Berkshire County. It is a volunteer-driven, non-profit corporation. This organization is involved in local historical research that also offers a variety of educational programs for every age group.

13. Chesterwood

Beautiful estate and home of Daniel Chester French, sculptor of the Lincoln Memorial. Visit the studio, garden, woodland walk, and museum shop of the Chesterwood in Stockbridge. May-Oct, Daily 10-5.

Visit the Hancock Shaker Village14. Hancock Shaker Village

200-year-old original Shaker village in Hancock. 21 historic buildings, Shaker furniture, round stone barn and craft demonstrations. Informative tours offered daily at the Hancock Shaker Village.

15. African American Heritage Trail

African American Heritage Trail encompasses 29 towns of the upper Housatonic valley. The trail is one of the more historic Berkshire activities in the area and celebrates African Americans who played pivotal roles such as W.E.B. Du Bois, James Weldon Johnson, Reverend Samuel Harrison, James Van Der Zee. Elizabeth Freeman (known as Mum Bett) was born into slavery circa 1744 and came to the Sheffield home of Col. John Ashley. Visit the John Ashley House to learn more. Upon hearing the Declaration of Independence read aloud in the village of Sheffield, Mum Bett determined that she, too had the inalienable right to freedom. She was granted the right of freedom after her famous meeting with Theodore Sedgwick. The Sedgwick house is in Sheffield village, a short walk from the Staveleigh House Inn. The successful suit was instrumental in ending slavery in Massachusetts 2 years later.

Outdoor Things to Do in the Berkshires

The Berkshires16. Bash Bish Falls

The highest waterfall in Massachusetts, the Bash Bish Falls are located in Mt. Washington State Forest.

17. Ski Butternut

Ski Butternut is one of the best options for winter activities in the Berkshires. Winter Family Skiing, XC Skiing, Summer Concerts, Arts Festival, Fireworks, Berkshire Mountain Music Festival, Berkshire Jazz Festival and more in Great Barrington.

18. Ski Catamount

You might not believe that you can find so much great skiing and riding so close to home. But you can, right here in the Berkshires- at Catamount! Ski Catamount is located in Hillsdale, NY.

19. Beartown State Forest

A 12,000-acre park with an extensive network of trails for hiking and cross-country skiing. Benedict Pond offers facilities for swimming, boating, and fishing. It is a perfect spot to view the fall foliage. Beartown State Forest is located in Monterey.

20. Bartholomew’s Cobble

A 100-foot-high bedrock outcropping with an amazing view of the lush and unique landscape. Designated a National Natural Landmark, Bartholomew’s Cobble is a popular year-round destination for hiking, wildlife viewing and exploring the beautiful Berkshires.

See amazing cars at the Lime Rock Historic Festival21. Lime Rock Park

If you want something a little different from hiking, a track day at Lime Rock Park might be just the thing! This historic raceway in nearby Lakeview, CT, hosts annual car shows, including the famous Lime Rock Historic Festival, races, autocross, track days, and more. If you’re interested in visiting the track during your stay, let us know – we offer a Lime Rock Drivers Special, and Mike can give you tips on how to get the most out of your track day, as he frequently participates himself.

22. Catamount Adventure Park

An aerial forest rope course consisting of platforms installed in the trees with ropes and cables connecting them to form “a bridge”. The goal is to move from tree platform to tree platform walking over the different secured bridges to complete the course. Catamount Adventure Park is located in Hillsdale, NY

23. Monument Mountain

A 503-acre reservation with 3 miles of trails that range from moderate to fairly difficult. The summit offers breathtaking views of the surrounding countryside. Monument Mountain is located in Great Barrington.

24. Berkshire South Recreation

Hiking, canoeing, fitness center, swimming pools and other summer activities the Berkshires are known for are available at Berkshire South Recreation.

25. October Mountain State Forest

With 16,627 acres to explore, nearby October Mountain is the largest state forest in Massachusetts. The October Mountain State Forest is great for hiking, fishing, and canoeing.

26. Berkshire Visitors Bureau

More information on all Berkshire attractions are available at the Berkshire Visitors Bureau site.

27. Berkshires Winter Activities

The Berkshire County of Massachusetts is one place that stands apart from all the rest in terms of winter attractions. Our corner of the state is both rich with culture and brimming with picturesque landscapes. From gorgeous state parks and mountain trails to lively festivals and historical sites, there are plenty of things to do in the Berkshires in the winter that are enjoyable for visitors of all backgrounds and ages. Take a look at the activities below to see exactly what makes this place so unique.

Shopping in the Berkshires

Couple Exploring Stores in Great Barrington MA28. Prime Outlets in Lee

Nestled in the hills of Western Massachusetts, Prime Outlets – Lee features tax-free outlet shopping at the scenic Gateway to the Berkshires in Lee.

39. Antiques in the Berkshires

Southwestern Massachusetts in general, and the towns along Route 7 in particular, go back to the colonial times and have become known as fertile ground for antique hunters to find fantastic antiques in the Berkshires. The area has been referred to as “Antiques Mecca” by Leslie and Leigh Keno, the Americana Gurus frequently seen on the television show “Antiques Road Show”.

In past times, this area was known primarily for American antiques. There are still many long-term and well-established Americana dealers among the almost 60 shops strung along the Route 7 area. More recently dealers who specialize in antiques from around the world have settled here to take advantage of the tradition. Today you will find dealers specializing in French, English, Canadian, Italian, Scandinavian and even Chinese antiques. These dealers feature all types of antiques, from furniture to paintings, folk art to brass candlesticks and Dutch Delftware to garden ornaments.

Nearby Berkshires Schools

30. Berkshire School

The mission of Berkshire School in is to provide young men and women with the intellectual and moral foundations and the leadership skills that will enable them to flourish as members of a family and a community as they confront the challenges of college and beyond. Located in Sheffield.

31. Bard College at Simon’s Rock

Students of this school receive a broad-minded, paradigm-shifting education; faculty trained in the country’s best universities; inspired and inspiring classes; first-class facilities for the sciences, the arts, and athletics; and an astonishing range of opportunities for conducting specialized research and gaining hands-on experience. Bard College at Simon’s Rock is located in Great Barrington.

32. Hotchkiss School

The Hotchkiss School is an independent boarding school located in Lakeville, Connecticut. Founded in 1891, the school provides an education of unsurpassed quality to 587 students in grades 9 through 12, and to a small number of postgraduates. Students at Hotchkiss School come from across the United States and 31 foreign countries. Graduates attend many of the most selective universities and colleges. Located in Lakeville, CT.

33. Salisbury School

Salisbury School instills in boys a vibrant enthusiasm for learning and the self-confidence needed for intellectual, physical, moral and spiritual development. Built on essential core values, the School’s unique culture promotes brotherhood, creativity, empathy, humility, integrity, leadership and respect. Salisbury School graduates men of character and promise who are prepared to meet the challenges of college and adulthood and to make a difference in an entrepreneurial, technological and cosmopolitan world. Located in Salisbury, CT.

Places to Stay in the Berkshires

The answer to the question of where to stay in the Berkshires is pretty easy. Stay with us at Staveleigh House! Our beautiful bed and breakfast in the Berkshires is a more relaxed, restful, and personal experience than staying at other hotels in the Berkshires. And for even more recommendations on things to do in the Berkshires, be sure to download a copy of our free Berkshires Vacation Guide!

Find Your Room

Connect with Staveleigh House Bed and Breakfast via social media!