• “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,…

  • Clock Tower Artists Open Studios

    Clock Tower Artists 75 South Church Street, 3rd Floor, Pittsfield, MA, United States

    September at the Clock Tower Artists Friday, September 5, 5 to 8 pm Saturday, September 13, 1 to 4 pm A new month, a new season approaching, and endless new inspiration! Step into…

  • 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.…

  • First Fridays at Five: Stunt Comedian WackyChad!

    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. Stunt Comedian WackyChad! will perform…

  • Free Drop-In Art Making at First Fridays at Five

    Berkshire Art Center 141 North Street, Pittsfield, MA, United States

    The Berkshire Art Center (BAC), 141 North Street, will host Free Drop-In Art Making during First Fridays at Five on Friday, September 5 from 5:30 to 7:30 pm. Enjoy a…

  • Summit Sounds with the Housie Shakers

    Bousquet Mountain 101 Dan Fox Drive, Pittsfield, MA, United States

    Enjoy an outdoor concert like no other… Start with a beautiful scenic chairlift ride to the summit, enjoy a delicious locally sourced meal, some amazing beer and wine, and live…