• 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…

  • May 1 First Fridays Artswalk

    Downtown Pittsfield Pittsfield, MA, United States

    The First Fridays Artswalk in downtown Pittsfield begins its 5-month season (May through September) on Friday, May 1 from 5 to 8 pm as part of the City of Pittsfield’s First Fridays…

  • First Fridays: Kids’ Bike Rodeo

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

    There will be a Kids’ Bike Rodeo in the Palace Park Parking Lot on Friday, May 1, from 5 to 8 pm, presented by the Berkshire Bike Path Council, AAA, and Massachusetts Safe Routes to School in honor of Bike Month.   This event is open to young riders, elementary and middle school children, and…

  • Family Fun Zone at First Fridays at Five

    Downtown Pittsfield Pittsfield, MA, United States

    The Family Fun Zone at First Fridays at Five will feature free, interactive activities from local non-profit organizations including arts & crafts, games, and more. Participating organizations include ALZ.0rg, Barrington…

  • 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.

  • 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

    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 food vendors within the vicinity. The Housie Shakers bring a variety of styles to the mix, with wide-ranging covers and original music spanning rock, blues,…

  • First Fridays at Five: artistic face painting with Melissa Matsuki Lillie

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

    Palace Park will feature free artistic face painting with Melissa Matsuki Lillie of Chroma Chameleon. Melissa Matsuki Lillie is painter whose artwork references natural forms using a personal visual language of vibrant colors and complex layers to reflect on the macroscopic and microscopic world. Her paintings evoke a sense of space that has been flattened…

  • Family Fun Zone at First Fridays at Five

    Downtown Pittsfield Pittsfield, MA, United States

    The Family Fun Zone at First Fridays at Five will feature free, interactive activities from local non-profit organizations including arts & crafts, games, and more.   Participating organizations include 914 LOCK INC, ALZ.0rg, Barrington Stage Company, BART Charter Public School, Berkshire Art Center, Berkshire Athenaeum, Berkshire Coalition for Suicide Prevention, Berkshire County Football Officials Association,…

  • June First Fridays at Five

    Downtown Pittsfield Pittsfield, MA, United States

    The City of Pittsfield, Downtown Pittsfield, Inc. (DPI), and the Downtown Pittsfield Cultural Association (DPCA) have announced details for the second First Fridays at Five of the 2026 season. The event on Friday, June 5 presented by MountainOne, will feature live music and dance, art, family fun, shopping, food, and entertainment throughout downtown Pittsfield. Attendees…