• Massachusetts Tax-Free Weekend 2026

    Downtown Pittsfield Pittsfield, MA, United States

    The Massachusetts Tax-Free weekend for 2026 is scheduled for Saturday, August 8, and Sunday, August 9. During this annual sales tax holiday, the state’s 6.25% sales tax is waived for most individual retail items priced at $2,500 or less purchased for personal use. You can check official guidelines and updates directly on the Mass.gov Sales…

  • Rhythmscape: Soul Line Dancing with Berkshire Sole Society

    Dunham Mall 100 North Street

    “Rhythmscape” on Dunham Mall highlights a different rhythm and instructor from our local community each session, reflecting the many identities that make Pittsfield home. Rhythmscape is free and open to…

  • DPI Community Coffee Chat: Stop Marketing Alone

    Dunham Mall 100 North Street

    Downtown Pittsfield, Inc. (DPI) and 1Berkshire will host a DPI Community Coffee Chat on Wednesday, August 19, from 8 to 9:30 am, outside on Dunham Mall at 100 North Street. This is the fourth in an ongoing series of DPI Community Coffee Chats downtown open to representatives from small businesses and nonprofits in Pittsfield and…

  • Rhythmscape: Luana Dias David teaches Salsa

    Dunham Mall 100 North Street

    “Rhythmscape” on Dunham Mall highlights a different rhythm and instructor from our local community each session, reflecting the many identities that make Pittsfield home. Rhythmscape is free and open to…

  • First Fridays: “Art in the Park” with Jill McLean

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

    Join Downtown Pittsfield, Inc. and First Fridays Artswalk as they feature Jill McLean as the September “Art in the Park” artist. Jill will be drawing a large ink sketch of First Friday during the September 4 First Fridays at Five from 5 to 8 pm. As an unofficial finale to the 2026 season of the…

  • First Fridays at Five: Misty Blues

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

    Persip Park, 175 North Street, will feature a live performance by Misty Blues from 5 to 8 pm. Enjoy a beer garden from Hot Plate Brewing Co. and local food vendors within the vicinity.   2019 International Blues Challenge finalist, Misty Blues, is fronted by lead singer/band founder Gina Coleman. The band is based out…

  • First Fridays at Five: Andrew the Balloonatic

    Downtown Pittsfield Pittsfield, MA, United States

    Andrew the Balloonatic will be balloon twisting, crafting free balloon creations in front of Crawford Square at 137 North Street.

  • Downtown Pittsfield, Inc. announces Local Love Arts Festival

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

    For many years, Downtown Pittsfield, Inc. (DPI) has worked to create opportunities for local artists through programs such as Artscape, First Fridays Artswalk, the Let It Shine! Public Art Partnership, and the Emerging Artists Program. This fall, DPI is excited to take that commitment a step further by launching a brand-new event dedicated entirely to…