North Adams

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 a number of smaller art galleries, as well as a few mills and factory buildings that have been converted into artist studios. This city with a "small town" feel is always hosting festivals, downtown parades, and on most weekends, a farmers' market where locals shop, visit, and grab up in-season produce from their favorite farms. 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.