• Second Annual Pittsfield Parade Car Show

    McKay Street Parking Lot McKay Street, Pittsfield, MA, United States

    The Pittsfield Parade Committee is hosting its second annual Car Show to benefit the Pittsfield Parade! All cars are welcome! Entry fees are on a donation basis and all proceeds support the parade. Awards will be given at the end of the event. Food trucks and tented area.

  • Free Kids’ Paint & Sip – July 7

    Parklet at 53 North Street

    Downtown Pittsfield, Inc. will host a Free Kids’ Paint & Sip on Friday, July 7, 5 to 7 pm, in the outdoor seating area next to Hot Harry’s and in front of the Marketplace Cafe (53 North Street). This free summer-themed Paint & Sip is best suited for ages 5 to 12, although younger and…

  • July 7 First Fridays Artswalk

    Downtown Pittsfield Pittsfield, MA, United States

    The First Fridays Artswalk in downtown Pittsfield returns on Friday, July 7 from 5 to 8 pm. Enjoy an Art Market on Dunham Mall, live music in Persip Park, live art demonstrations, opening receptions, open studios, and a Swing Dance lesson in Palace Park with a live band! Also on July 7, the popular Free…

  • Fifth Annual Berkshire Jazz Showcase

    The Common, First Street, Pittsfield, MA 100 First Street, Pittsfield, MA, United States

    A free all-afternoon concert on Pittsfield's First Street Common, adjacent to the playground and splash park. The showcase features four of the finest jazz groups in the region: The Wanda…

  • Mountain Day with The Whiskey Treaty Roadshow

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

    Berkshire-based Americana/folk rock supergroup The Whiskey Treaty Roadshow and the Berkshire County Outdoor Recreation Summit are proud to announce the 2nd Annual Mountain Day at Bousquet Mountain on Saturday, July…

  • Free Kids’ Paint & Sip – August 4

    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, August 4, 5 to 7 pm, in the auditorium at St. Stephen’s…

  • Live Music: Robin O’Herin and Bernice Lewis

    Lichtenstein Center for the Arts 28 Renne Avenue, Pittsfield, MA, United States

    Robin O'Herin and Bernice Lewis Friday, August 4, 5 to 8 pm, FREE Lichtenstein Center for the Arts, 28 Renee Ave.   On Friday, August 4, Robin O’Herin and Bernice…

  • Live Painting Demo with Diane Firtell

    Framework by Downtown Pittsfield, Inc. 437 North Street, Pittsfield, MA, United States

    Live Painting Demo with Diane Firtell Friday, August 4, 5 to 8 pm, FREE FRAMEWORK, 437 North Street As part of the First Fridays Artswalk, Diane Firtell will be hosting a free live…

  • August 4 First Fridays Artswalk

    Downtown Pittsfield Pittsfield, MA, United States

    The First Fridays Artswalk in downtown Pittsfield returns on Friday, August 4 from 5 to 8 pm. Enjoy live music at the Lichtenstein Center for the Arts with sets by…