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  • The Rise With Pride Tour lands in Pittsfield!

    Featured
    WANDER Berkshires 34 Depot Street, Pittsfield, MA, United States

    Join Man Must Explore for a night of alternative rock, community, and celebration featuring support from Pittsfield's own alt-rock powerhouse Datura and a drag performance by the captivating Bella Santarella. […]

  • Laugh Out Loud

    Featured
    WANDER Berkshires 34 Depot Street, Pittsfield, MA, United States

    MTC Stands Up! Comedy Night Hosted by Remy Germinario at WANDER Jul 09, 2026, 7:00 PM – 8:10 PM Join the MTC 2026 cohort and Remy Germinario for a night […]

  • Ivy League of Comedy Tour

    Featured
    The Colonial Theatre 111 South Street, Pittsfield, MA, United States

    The Ivy League of Comedy is bringing the best of stand-up comedy to The Colonial Theatre, featuring Moody McCarthy, J-L Cauvin & Jane Condon!

    $30

  • An Evening with David Sedaris

    Featured
    The Colonial Theatre 111 South Street, Pittsfield, MA, United States

    Beloved bestselling author David Sedaris brings his signature sardonic wit and incisive social observation back to The Colonial Theatre.

    $60