• Downtown Pittsfield… It’s Alive! Kids’ Zone

    Lawn of St. Joseph's Church 414 North Street, Pittsfield, MA, United States

    Downtown Pittsfield… It’s Alive! Kids’ Zone: Saturday, October 18, 10 am to 1 pm The Downtown Pittsfield… It’s Alive! Kids’ Zone will be held on the St. Joseph’s Church lawn.…

  • Downtown Pittsfield… It’s Alive! Night Circus

    Dunham Mall 100 North Street +1 more

    Downtown Pittsfield… It’s Alive! Night Circus: Saturday, October 18, 3 to 6 pm, on Dunham Mall, School Street, and the portion of North Street that connects the two. The Downtown Pittsfield……

  • Night Circus: Free Tarot Readings with Emily Dunsay Wild

    90 North Studio 90 North Street, Pittsfield, MA, United States

    Enjoy free 3 Card Tarot Readings with master psychic, alchemist, life coach, and poet Emily Dunsay Wild inside 90 North Studio (90 North Street). The readings are free, but tips…

  • Depot After Dark: Teen Dance Party Edition!

    Liberty Street Liberty Street, Pittsfield, MA, United States

    Depot After Dark: Teen Dance Party Edition! will be held on Saturday, October 18, 7 to 9:30 pm, on Liberty Street (the alleyway between Tito’s/Wander and Crawford Square). Depot After Dark:…

  • Free Kids’ Harvest 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 Friday, November 7, from 5 to 7 pm, in the auditorium at St.…

  • 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…