If you're looking for a Berkshires getaway that combines culture with outdoor fun (and a cool place to stay), put North Adams on your short list. In addition to the Massachusetts Museum of Contemporary Arts (Mass MoCA), North Adams has mills and factory buildings that have been converted into artist studios. The Porches Inn, a row of eye-catching multihued Victorians, has added an additional helping of hip to downtown.
In addition, the 11-mile Ashuwillticook Rail Trail is easily accessible in nearby Adams, as is Mt. Greylock State Reservation, if you explore it on foot via one of the local trailheads.