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  • Makers Market at First Fridays at Five

    Makers Market at First Fridays at Five

    Downtown Pittsfield Pittsfield, MA, United States

    The Makers Market at First Fridays at Five will feature over a dozen local vendors selling handmade products such as crafts, clothing and accessories, candles, art, custom gift items, self-care…

  • First Fridays at Five: Jan Rapisarda Mural

    First Fridays at Five: Jan Rapisarda Mural

    Downtown Pittsfield Pittsfield, MA, United States

    On Friday, May 1, weather permitting, artist Jan Rapisarda will be at work on a new, large-scale mural at 7 North Street, and the public is invited to watch him…

  • First Fridays: Bowey the Clown

    First Fridays: Bowey the Clown

    Downtown Pittsfield Pittsfield, MA, United States

    Bowey the Clown will be crafting free balloon creations in front of Crawford Square at 137 North Street.

  • Downtown Pittsfield, Inc. (DPI) 2026 Annual Meeting

    Downtown Pittsfield, Inc. (DPI) 2026 Annual Meeting

    Zion Lutheran Church 74 1st Street, Pittsfield, MA, United States

    The Downtown Pittsfield, Inc. (DPI) Annual Meeting will be held Thursday, May 14 at The Common Room at the Zion Lutheran Church at 74 First Street in Pittsfield. There will be registration and networking…

  • DPI Community Coffee Chat

    1Berkshire 137 North Street, Suite 200, Pittsfield, United States

    DPI Community Coffee Chat Wednesday, May 20, 8 to 9:30 am 1Berkshire Boardroom at 137 North Street, Suite 200 Topic: Insurance 101 for Small Businesses Hosts: Rebecca Brien, DPI Kevin…

  • June 5 First Fridays Artswalk

    June 5 First Fridays Artswalk

    Downtown Pittsfield Pittsfield, MA, United States

    The First Fridays Artswalk in downtown Pittsfield continues its 5-month season (May through September) on Friday, June 5 from 5 to 8 pm as part of the City of Pittsfield’s First Fridays…

  • First Fridays at Five: The Housie Shakers

    First Fridays at Five: The Housie Shakers

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

    Persip Park, 175 North Street, will feature a live performance by The Housie Shakers from 5 to 8 pm. Enjoy a beer garden from Hot Plate Brewing Co. and local…

  • First Fridays at Five: Busker Robin O'Herin

    First Fridays at Five: Busker Robin O’Herin

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

    Busker Robin O'Herin will be popped up in Palace Park (near 122 North Street) from 5 to 8 pm. A three-time Boston Blues Finalist, and 2023 Albany Blues Challenge Finalist,…