• “Where’s Winston?” Scavenger Hunt at First Fridays at Five

    Downtown Pittsfield Pittsfield, MA, United States

    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,…

  • First Fridays at Five: Opal Raven Cirque

    Downtown Pittsfield Pittsfield, MA, United States

    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…

  • September 5 First Fridays at Five

    Downtown Pittsfield Pittsfield, MA, United States

    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.…

  • Depot After Dark: First Fridays Afterparty

    Liberty Street Liberty Street, Pittsfield, MA, United States

    After the September 5 First Fridays at Five, Downtown Pittsfield, Inc., Tito’s Mexican Bar & Grill, and Wander Berkshires will present “Depot After Dark” outside on Liberty Street (the alleyway…