• 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…

  • First Fridays: Busker Autumn Phoenix in Palace Park

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

    Busker Autumn Phoenix will be popped up in Palace Park (near 122 North Street) from 5 to 8 pm on Friday, May 1. Autumn an award-winning singer-songwriter who will be performing original material and some covers. She is also a professional photographer! In the case of inclement weather, music with Autumn Phoenix will be inside…

  • 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 Stage Company, BART Charter Public School, Berkshire Art Center, Berkshire Athenaeum, Berkshire Coalition for Suicide Prevention, Berkshire County Head Start, Berkshire County Kids Place, Berkshire…

  • 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 items, and packaged foods and sweets. Makers include ATK Customs, Auntie Kat’s Gift Shop, Bake My Day, Baked! Pastries & More, Berkshire Henna, BlossomBun, Braidy…

  • 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 create live during the First Fridays at Five. The new mural is a celebration of the people, recreation, nature, and wildlife that make our region…

  • 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

    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…