In February 2026, Downtown Pittsfield, Inc. will present “A Taste of Downtown” – a month-long Downtown Restaurant Celebration – in partnership with Mill Town Foundation. Seventeen restaurants and bars in downtown Pittsfield…
New for September, enjoy an Entertainment Zone at the south end of North Street near Hot Harry’s featuring performances by WackyChad! and Opal Raven Cirque. Stunt Comedian WackyChad! will perform…
The final First Fridays at Five of the 2025 season will be held on Friday, September 5th from 5 to 8 pm with an Afterparty from 8 to 11 pm.…
New for September, enjoy an Entertainment Zone at the south end of North Street near Hot Harry’s featuring performances by WackyChad! and Opal Raven Cirque. Opal Raven Cirque will perform a…
Downtown Pittsfield, Inc. will present a one-night-only Back-to-School edition of “Where’s Winston?” during the September 5th First Fridays at Five. This Back-to-School themed scavenger hunt for images of Officer Winston,…
The Makers Market at First Fridays at Five will be on North Street and will feature over a dozen local vendors selling handmade products such as crafts, clothing and accessories,…
The Family Fun Zone at First Fridays at Five will be on North Street and will feature free, interactive activities from local non-profit organizations including face-painting, arts & crafts, games,…
The Berkshire County Sheriff’s Office will be offering the Child ID Project at the September 5 First Fridays at Five. This free service creates a digital ID with fingerprints, photo,…
The First Fridays Artswalk in downtown Pittsfield concludes its 5-month season (May through September) on Friday, September 5 from 5 to 8 pm as part of the City of Pittsfield’s…
Discover Pittsfield’s Vibrant Street Art Scene! Whether you're an art lover, curious traveler, or local explorer, this lively 2-hour guided walking tour offers a dynamic look into the artists and…