Downtown Pittsfield Gift Card Pittsfield MA
Downtown Pittsfield Gift Card Pittsfield MA
Downtown Pittsfield Gift Card Pittsfield MA
Downtown Pittsfield Gift Card Pittsfield MA
Downtown Pittsfield MA Dine Dining Restaurants
Downtown Pittsfield Gift Card Pittsfield MA
Downtown Pittsfield Gift Card Pittsfield MA
Downtown Pittsfield MA Professional Theatre
Downtown Pittsfield Gift Card Pittsfield MA
Downtown Pittsfield Gift Card Pittsfield MA
Shop Small, Shop Downtown Pittsfield MA
Downtown Pittsfield Gift Card Pittsfield MA
Downtown Pittsfield Gift Card Pittsfield MA
First Fridays Artswalk in Downtown Pittsfield, MA
HeartOfTheBerkshiresBorderNEWLOGO

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!

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!

Hey, Neighbor!

Hey, Neighbor!

Hey Neighbor! When’s the last time you visited downtown Pittsfield? Exciting experiences await you – Explore new shops. Enjoy global cuisine, community festivals, world-class theatre,…

Read more

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!