• Festive Frolic: Kids’ Paint & Sip

    St. Stephen’s Episcopal Church 67 East Street, Pittsfield, MA, United States

    Downtown Pittsfield, Inc. and St. Stephen’s Episcopal Church will host a Free Kids’ Paint & Sip on Saturday, December 6, 12:30 to 3 pm, in the auditorium at St. Stephen’s…

  • Festive Frolic: Photo Ops with Santa

    Dunham Mall 100 North Street

    NOW INSIDE!! Downtown Pittsfield, Inc. will host Photo Ops with Santa on Saturday, December 6, 12:30 to 3 pm, inside Hand Crafted at 26 Dunham Mall. Santa will be welcoming…

  • “A Taste of Downtown” – a month-long Downtown Restaurant Celebration

    Downtown Pittsfield Pittsfield, MA, United States

    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…

  • Downtown Pittsfield Spring Cleanup

    Downtown Pittsfield Pittsfield, MA, United States

    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…

  • Free Children’s Spring Tea Party and Paint & Sip

    WANDER Berkshires 34 Depot Street, Suite 101., Pittsfield, MA, United States

    Free Children’s Spring Tea Party and Paint & Sip at WANDER on Sunday, April 19, from 2 to 4 pm. Downtown Pittsfield, Inc. (DPI) will host a free Downtown Celebrates Spring Children’s…

  • Kids’ Spring Fest in Dunham Mall (Celebrates Spring!)

    Dunham Mall 100 North Street

    Join Downtown Pittsfield, Inc., the Berkshire Museum, and BeatNest for a Spring gathering outside on Dunham Mall at 100 North Street. The Berkshire Museum will bring objects from their education…

  • The Berkshires Music Mixer

    WANDER Berkshires 34 Depot Street, Suite 101., Pittsfield, MA, United States

    Hosted by Berkshires-born recording artist and music producer Jackson Whalan, the goal of The Berkshires Music Mixer is to bring the entire local music industry together. This is a space…

  • First Fridays at Five: Nate Martel and Band

    Persip Park 175 North Street, Pittsfield, MA, United States

    Persip Park, 175 North Street, will feature a live performance by Nate Martel and his band from 5 to 8 pm. Enjoy a beer garden from Hot Plate Brewing Co. and local food vendors within the vicinity. Powerhouse vocalist, songwriter, and guitarist, Nate Martel, currently resides in Easthampton, MA, but he was born and raised…

  • First Fridays at Five: Beer Garden and busker Micheal Aaron

    School Street, Pittsfield MA

    School Street will feature a Beer Garden with Hot Plate Brewing Co., lawn games, and busker, Micheal Aaron from 5 to 8 pm. Michael Aaron is not just another singer-songwriter; he's a musical craftsman whose eclectic blend of folk and indie rock reflects a lifetime of diverse experiences and influences. Drawing inspiration from a diverse array…

  • First Fridays: “Art in the Park” with Peter Vacchina

    Palace Park 116 North Street, Pittsfield, MA, United States

    Downtown Pittsfield, Inc. and First Fridays Artswalk will feature Peter Vacchina as the May “Art in the Park” artist.   Peter will be popped up in Palace Park (near 122…