Berkshire Attractions and Things to Do

Red CurrantsThere 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. Outdoor enthusiasts will find miles and miles of trails for hiking and biking, rivers and lakes to explore and slopes for skiing in winter. Hungry visitors will find a multitude of outstanding restaurants offering great food made from locally grown ingredients.

Video courtesy of the Berkshire Visitor’s Bureau

Close to our Sheffield 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. There is also a wonderful array of antique stores to poke about in and find a treasure or two. Other attractions are just a short drive away.

Be sure to download our Vacation Guide for even more information on our area!

Music & Dance in the Berkshires

1. Tanglewood – Tanglewood is the idyllic Berkshire summer home of the Boston Symphony Orchestra. June through Labor Day, Tanglewood offers classical, jazz and popular concerts daily in Lenox.

2. Jacob’s Pillow Dance Festival – For over 70 years, this 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 – This Stockbridge museum 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 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.

Tasting Rooms in the Berkshires

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

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.

The Best Restaurants in the Berkshires

8. Aegean Breeze – Mediterranean and Greek cuisine casual dining in Great Barrington. Lunch, dinner with daily specials. Entrees include souvlaki, seafood, gyro, pasta, steak, chicken. Open 7 days 11am-11pm.

9. Allium – Farm-to-table seasonal menu featuring contemporary American cuisine.

10. Baba Louie’s Pizza – Wood fired organic sourdough pizza topped with the freshest ingredients; soups, salads, and sandwiches also available.

11. Barrington Brewery & Restaurant – Recommended by Zagat’s, AAA, Frommers, its recipes are in Bon Appetit’s 50th Anniversary Edition book. Inexpensive kids menu, handcrafted beer, and outside dining in Great Barrington.

12. Bistro Box – An old time roadside eatery serving, lunch, lunchboxes, veggie fare and family favorites in Great Barrington.

13. Bizen Japanese Restaurant – Gourmet world-class sushi and authentic Japanese cuisine

14. Berkshire Co-op Market – Natural foods store & café featuring local & organic produce, meat & seafood, prepared foods & extensive wellness department. Open to all in Great Barrington!

15. Castle Street Café – A comfortable bar and restaurant in Great Barrington serving a unique menu featuring local fare. Live Jazz on Friday and Saturday nights.

16. Market Place Cafe – At the Marketplace Cafe, you can enjoy a variety of signature sandwiches made fresh, custom-made oven baked flatbread, pizzas, refreshing hand tossed salads and Lattes. It’s a three-minute walk from Staveleigh House and a great place to shop for picnic foods.

17. Stage Coach Tavern – Zagat Survey quoted ” This ‘time stood still’ tavern in a stately Federalist farm house is a winner among city weekenders. Reasonably priced American vittles are simply prepared but delicious! Just what comfort food should be.”

Theater in the Berkshires

18. Berkshire Theatre Group – Live music, comedy, dance, family shows and more at the Unicorn, Colonial, and Fitzpatrick Theatres in Pittsfield and Stockbridge.

19. Mahaiwe Performing Arts Center – Year-round arts center in restored historic theater presenting live music, theater, dance and family programs as well as classic films.

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

21. Barrington Stage Company – Award winning theater on three stages in Pittsfield.

History of the Berkshires

22. 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.

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

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

25. African American Heritage Trail – African American Heritage Trail encompasses 29 towns of the upper Housatonic valley. The trail 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 Berkshires26. Bash Bish Falls – The highest waterfall in Massachusetts, located in Mt. Washington State Forest.

27. Ski Butternut – Winter Family Skiing, XC Skiing, Summer Concerts, Arts Festival, Fireworks, Berkshire Mountain Music Festival, Berkshire Jazz Festival and more in Great Barrington.

28. 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! Located in Hillsdale, NY.

29. 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. Located in Monterey.

30. 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.

31. 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. Located in Hillsdale, NY

32. 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. Located in Great Barrington.

33. Berkshire South Recreation – Hiking, canoeing, fitness center, swimming pools.

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

35. Berkshire Visitors Bureau – More information on all Berkshire attractions are available at this site.

Shopping in the Berkshires

36. Prime Outlets – 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.

37. Antiques – 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. 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

38. 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.

39. 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. Located in Great Barrington.

40. 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 come from across the United States and 31 foreign countries. Graduates attend many of the most selective universities and colleges. Located in Lakeville, CT.

41. 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 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.

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