Welcome to Downtown Pittsfield, Massachusetts!
Designated one of the Cultural Districts in Massachusetts, Pittsfield’s downtown, known as the Upstreet Cultural District, boasts a lively roster of music, dance, theatre, community festivals, and celebrations, including two highly acclaimed professional theatres – the Colonial Theatre, part of Berkshire Theatre Group, and Barrington Stage Company. There’s a vibrant visual arts scene in Pittsfield too, with public art, artist studios and cooperatives, and the First Fridays Artswalk. Cultural festivals include First Fridays at Five, Berkshire Pride, Pittsfield CityJazz Festival, 10×10 Upstreet Arts Festival, and more!