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, 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 the First Fridays Artswalk. Cultural festivals include First Fridays at Five, the WordXWord Festival, Pittsfield CityJazz Festival, 10X10 Upstreet Festival, and more!

Getting to Pittsfield

Find out how to get to Downtown Pittsfield, where to park, and where to go.

Downtown Dining

Downtown Pittsfield boasts an exciting dining scene with cuisine representing 4 different continents. Our eclectic cafés have breakfast, lunch, and coffee covered, and many of our downtown restaurants serve food and drink late into the evening and feature live music!

Unique Shopping

Our downtown Pittsfield retailers have shelves fully-stocked with housewares, decor, clothing, jewelry, toys, one-of-a-kind local handmade items, candles, art, and much more that you won’t find in the big box stores! Keep dollars local!

What’s Happening

Mark your calendars for upcoming events in Downtown Pittsfield!

Reimagine Dunham Mall!

Reimagine Dunham Mall!

The Downtown Pittsfield Cultural Association, with partners the City of Pittsfield, MassDevelopment’s Transformative Development Initiative (TDI), Downtown Pittsfield, Inc. (DPI), and the Pittsfield Community Design…

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Major Donors are committed to the vitality of downtown and our organization. They allow us to achieve the goals outlined in the Strategic Plan and our mission statement.

Special thanks to our Platinum Level donors below!