May 1 First Fridays Artswalk
May 1 First Fridays Artswalk The First Fridays Artswalk in downtown Pittsfield begins its 5-month season (May through September) on Friday, May 1 from 5 to 8 pm as part of…
May 1 First Fridays at Five
The City of Pittsfield, Downtown Pittsfield, Inc. (DPI), and the Downtown Pittsfield Cultural Association (DPCA) have announced details for the first First Fridays at Five of the 2026 season. The…
Downtown Pittsfield Celebrates Spring Week (April 18-26) Features Events for All Ages
Downtown Pittsfield Celebrates Spring Week Features Events for All Ages Downtown Pittsfield, Inc. (DPI) is pleased to present their fourth annual Downtown Celebrates Spring Week, April 18-26, offering free and low-cost programming to individuals and families…
Downtown Pittsfield Spring Cleanup
Downtown Pittsfield, Inc. will host our Annual Downtown Pittsfield Spring Cleanup on Friday, April 17, 12 to 4 pm. Early check-in/pick-up of trash bags will be available starting at 11…
“A Taste of Downtown” – a month-long Downtown Restaurant Celebration
“A Taste of Downtown” – a month-long Downtown Restaurant Celebration In February 2026, Downtown Pittsfield, Inc. will present “A Taste of Downtown” – a month-long Downtown Restaurant Celebration –…
VOTE in our Winter Window-land Decorating Contest
Winter Window-land Decorating Contest: December 16 through December 27 Downtown Pittsfield, Inc. (DPI) has announced that voting for their Winter Window-land Decorating Contest will be open December 16 through…
Downtown Pittsfield Festive Frolic
Downtown Pittsfield Festive Frolic: Friday and Saturday, December 5 and 6 Downtown Pittsfield, Inc. (DPI) will host the Downtown Pittsfield Festive Frolic on Friday and Saturday, December 5 and…
Shop to Win! Small Business Weekend Digital Passport
Shop to Win with our Small Business Weekend Digital Passport! Shop Small Friday, November 28 through Sunday, November 30 for a chance to win 1 of 2 prizes – a…
Downtown Pittsfield… It’s Alive! 2025
Downtown Pittsfield, Inc.’s Downtown Pittsfield… It’s Alive! celebrates the Halloween season! This year’s event will be on Saturday, October 18 and will feature 3 parts: 1. A Kids’…
September 5 First Fridays at Five
September 5 First Fridays at Five The City of Pittsfield, Downtown Pittsfield, Inc. (DPI), and the Downtown Pittsfield Cultural Association (DPCA) have announced details for the final First Fridays at…