Best events in

Cheshire

While the Berkshires operate on a distinct seasonal rhythm, there are always compelling events and things to do in the Cheshire, MA area. The region blends rural charm with world-class cultural institutions, from repurposed mills in North Adams to gilded-age theaters in Pittsfield. This unique character means an outing can involve anything from a quiet hike to an internationally acclaimed performance.

• For a lively, walkable downtown experience, Great Barrington offers a 'funky' scene with independent shops and restaurants that serve as a prelude to a show.
• Explore the massive galleries at MASS MoCA in North Adams, a contemporary arts center that also hosts events like the FreshGrass Festival.
• Catch a classic or new play at one of the region's renowned theater venues, such as Shakespeare & Company in Lenox or Barrington Stage Company in Pittsfield.