Berkshire Theatre Group’s Colonial Theatre in Pittsfield MA. Courtesy of BTG.
Berkshire Theatre Group’s production of The Music Man, 2017. Photo by Emma K. Rothenberg-Ware.

Designated one of the Cultural Districts in Massachusetts, Pittsfield’s downtown, known as the Upstreet Cultural District, boasts a lively roster of music, dance and theater, community festivals, and celebrations, including two highly acclaimed professional theaters—the Colonial Theatre, part of Berkshire Theatre Group, and Barrington Stage Company—presenting a wide array of performances. There’s a vibrant visual arts scene in Pittsfield, too, with public art, thriving galleries, artist studios, cooperatives, and monthly First Fridays Artswalk. Cultural festivals include 3rd Thursdays, the WordXWord Festival, Pittsfield CityJazz Festival, 10X10 Upstreet Festival, and more.