• Depot After Dark: Teen Dance Party Edition!

    Liberty Street Liberty Street, Pittsfield, MA, United States

    Depot After Dark: Teen Dance Party Edition! will be held on Saturday, October 18, 7 to 9:30 pm, on Liberty Street (the alleyway between Tito’s/Wander and Crawford Square). Depot After Dark:…

  • Free Kids’ Harvest Paint & Sip

    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, November 7, from 5 to 7 pm, in the auditorium at St.…

  • Wandering Dance Festival: November 9-15

    Festival attendees can take part in free workshops, learn from esteemed choreographers, and showcase their own talents during open dance sessions. Stay tuned to milltownfoundation.org/wandering-dance-festival for more information!

  • XWA Superstars of Wrestling return to Pittsfield

    Masonic Temple 116 South Street, Pittsfield, MA, United States

    Get ready, Pittsfield! XWA Wrestling is back with another night of high-impact, family-friendly action you won’t want to miss! Advance Ticket Special: Kids 10 & under – ONLY $10 Adults…

  • Festive Frolic: Free Hot Chocolate and Photo Ops with the Grinch

    Otto’s Kitchen & Comfort 95 East Street, Pittsfield, MA, United States

    Otto’s Kitchen & Comfort, 95 East Street, will be providing free hot chocolate and photo ops with the Grinch from 5 to 8 pm on Friday, December 5. Stop by before or after the Park Square Tree Lighting Ceremony! This event is a part of the Festive Frolic which is happening on Friday, December 5…

  • Festive Frolic: Park Square Tree Lighting Ceremony

    Park Square

    The City of Pittsfield’s Park Square Tree Lighting Ceremony will be on Friday, December 5 starting at 6 pm. Join Santa, Mrs. Claus, and the City of Pittsfield’s Recreation Department…

  • Festive Frolic: The Berkshire Bazaar at The Holiday Inn

    The Holiday Inn & Suites 1 West Street, Pittsfield, MA, United States

    The Festive Frolic continues Saturday, December 6, with The Berkshire Bazaar hosted by Thistle ‘n Thorn Floral at The Holiday Inn, 1 West Street, from 11 am to 4 pm. Shop handmade goods and thoughtful gifts from dozens of local makers, artists, and small businesses. Enjoy a complimentary cocoa bar (while supplies last!), free photo station, and…

  • Festive Frolic: Free Drop-in Crafts at The Berkshire Athenaeum

    Berkshire Athenaeum 1 Wendell Avenue, Pittsfield, MA

    The Berkshire Athenaeum, Pittsfield’s Public Library, 1 Wendell Avenue, will offer free drop-in activities for all ages from 12:30 to 3 pm on Saturday, December 6. The Children’s Library will host a fun winter craft, the Young Adult Department will offer a button-making craft, and there will be festive bookmark making for adults and teens…

  • Free Ride Day at The Berkshire Carousel

    The Berkshire Carousel 50 Center Street, Pittsfield, MA, United States

    It's Donkey Day on Saturday, December 6! There will be free rides in celebration of Missy the Donkey sponsored by author Kevin O’ Hara. Kevin will introduce and sign his latest…