Quick Summary:

  • Where are The Berkshires located?
    • The Berkshires are situated in the beautiful mountains of Western Massachusetts.
    • The area is within easy traveling distance from New York City, Boston, and Albany.
  • What makes The Berkshires a popular vacation destination?
    • The region offers a great mix of outdoor recreation, arts, culture, and fine dining.
    • It has a thriving farm-to-fork restaurant scene featuring fresh local ingredients.
    • There are several excellent museums and art galleries for visitors to explore.
  • What outdoor activities can visitors enjoy?
    • The Berkshires offer hiking, mountain biking, and canopy tours in the warmer months.
    • During the winter, the area is a popular skiing destination.


  • Updated with new information since originally published.
  • Please support our journalism through affiliate links. Affiliate Disclosure
  • Our editors recommend these diverse local experiences.

1. Monument Mountain Reservation ⭐⭐⭐⭐⭐

Category: Activities
Monument Mountain Reservation | Things to Do in the Berkshires, Massachusetts
© Courtesy of jdwfoto - Fotolia.com

2. Hancock Shaker Village ⭐⭐⭐⭐⭐

Hancock Shaker Village | Things to Do in the Berkshires, Massachusetts
© Courtesy of sphraner - Fotolia.com

3. Berkshire Botanical Garden

Category: Activities
Berkshire Botanical Garden | Things to Do in the Berkshires, Massachusetts
© Courtesy of Michael Meijer - Fotolia.com

4. Berkshire Museum

Category: Museums & Culture
Berkshire Museum | Things to Do in the Berkshires, Massachusetts
© Berkshire Museum

5. Bousquet Ski Area

Category: Activities
Bousquet Ski Area | Things to Do in the Berkshires, Massachusetts
© Courtesy of kapichka - Fotolia.com

6. Catamount Aerial Adventure Park

Tours
Catamount Aerial Adventure Park | Things to Do in the Berkshires, Massachusetts
© Courtesy of Studio KIVI - Fotolia.com

7. Catamount Ski Area

Category: Activities
Catamount Ski Area | Things to Do in the Berkshires, Massachusetts
© Courtesy of michelangeloop - Fotolia.com

8. Chesterwood Museum

Category: Museums & Culture
Chesterwood Museum | Things to Do in the Berkshires, Massachusetts
© Chesterwood Museum

9. The Clark Art Institute

Category: Museums & Culture
The Clark Art Institute | Things to Do in the Berkshires, Massachusetts
© The Clark Art Institute

10. Furnace Brook Winery at Hilltop Orchards

Category: Activities
Furnace Brook Winery at Hilltop Orchards | Things to Do in the Berkshires, Massachusetts
© Furnace Brook Winery at Hilltop Orchards

11. The School at Jacob's Pillow

The School at Jacob's Pillow | Things to Do in the Berkshires, Massachusetts
© Courtesy of master1305 - Fotolia.com

12. Jiminy Peak Mountain Resort

Category: Accommodations
Jiminy Peak Mountain Resort | Things to Do in the Berkshires, Massachusetts
© Courtesy of Delphotostock - Fotolia.com

13. Onota Lake

Category: Activities
Onota Lake | Things to Do in the Berkshires, Massachusetts
© Courtesy of jdwfoto - Fotolia.com

14. Pleasant Valley Wildlife Sanctuary

Category: Activities
Pleasant Valley Wildlife Sanctuary | Things to Do in the Berkshires, Massachusetts
© Courtesy of duke2015 - Fotolia.com

15. MASS MoCA

MASS MoCA | Things to Do in the Berkshires, Massachusetts
© MASS MoCA

16. Mount Greylock State Reservation

Category: Activities
Mount Greylock State Reservation | Things to Do in the Berkshires, Massachusetts
© Courtesy of jdwfoto - Fotolia.com

17. Natural Bridge State Park

Category: Activities
Natural Bridge State Park | Things to Do in the Berkshires, Massachusetts
© Courtesy of k_samurkas - Fotolia.com

18. Naumkeag

Naumkeag | Things to Do in the Berkshires, Massachusetts
© Courtesy of eks_design - Fotolia.com

19. Norman Rockwell Museum

Category: Museums & Culture
Norman Rockwell Museum | Things to Do in the Berkshires, Massachusetts
© Norman Rockwell Museum

20. Pittsfield State Forest

Category: Activities
Pittsfield State Forest | Things to Do in the Berkshires, Massachusetts
© Courtesy of jdwfoto - Fotolia.com

21. Ski Butternut

Category: Activities
Ski Butternut | Things to Do in the Berkshires, Massachusetts
© Courtesy of U. J. Alexander - Fotolia.com

22. The Mount (Edith Wharton’s Home)

Category: Activities
The Mount (Edith Wharton’s Home) | Things to Do in the Berkshires, Massachusetts
© The Mount (Edith Wharton’s Home)

23. Ventfort Hall Mansion and Gilded Age Museum

Category: Museums & Culture
Ventfort Hall Mansion and Gilded Age Museum | Things to Do in the Berkshires, Massachusetts
© Ventfort Hall Mansion and Gilded Age Museum

24. Williams College Museum of Art

Category: Museums & Culture
Williams College Museum of Art | Things to Do in the Berkshires, Massachusetts
© Williams College Museum of Art

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