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 multihue Victorians, has added "hip" to downtown. The 11-mile Ashuwillticook Rail Trail is accessible in nearby Adams, as is Mt. Greylock State Reservation, if you venture there on foot via one of the local trailheads.
There seems to be something about this remote collection of islands that fosters the rare, the fearless, and above all, the weird.More