• Free Hot Chocolate and Photo Ops with the Grinch

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

    Otto’s Kitchen & Comfort will be providing free hot chocolate and photo ops with the Grinch from 5 to 8 pm on Friday, December 1! Stop by before or after…

  • December 1 First Fridays Artswalk

    Downtown Pittsfield Pittsfield, MA, United States

    December 1 First Fridays Artswalk features New Art Exhibits, Open Studios, Wreath Art Auction, and Free Admission to the Festival of Trees!   The First Fridays Artswalk in downtown Pittsfield…

  • Free Admission to the Festival of Trees!

    Berkshire Museum 39 South Street, Pittsfield, MA, United States

    The Berkshire Museum will offer free admission to the Festival of Trees: Nostalgia on Friday, December 1, 5 to 8 pm. This free event is sponsored by the Museum’s Board of Trustees.…

  • Holiday Tree Lighting Ceremony

    Park Square

    Join Santa, Mrs. Claus, and the City of Pittsfield’s Recreation Department for this festive holiday tradition! Don’t forget to stop by Otto’s to grab your FREE hot chocolate anytime from…

  • Free Kids’ Paint & Sip (Festive Frolic Junior)

    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 Saturday, December 2, 12 to 3 pm, in the auditorium at St. Stephen’s…

  • Santa at The Beacon Cinema (Festive Frolic Junior)

    The Beacon Cinema 57 North Street, Pittsfield, MA, United States

    Saturday’s Festive Frolic Junior events will be headlined by Santa at The Beacon Cinema sponsored by Phoenix Theatres and Downtown Pittsfield, Inc. from 12 to 3 pm. All children are welcome to take a free professional photo with Santa which will be made available for download after the event. This event is a part of…

  • Festive Frolic LEGO Drop-in at Bottomless Bricks

    Bottomless Bricks 163 South Street, Suite 4., Pittsfield, MA, United States

    Explore building with LEGO® bricks and take home a festive coloring sheet! Build a heart and share the joy with LEGO® #BuildToGive For each heart you build and share on social media, LEGO® will donate a LEGO® set to a child in need of play this holiday season. LEGO® is a trademark of the LEGO®…

  • “Santa: My Life & Times” Reading and Giveaway at the Berkshire Athenaeum

    Berkshire Athenaeum 1 Wendell Avenue, Pittsfield, MA

    The Berkshire United Way staff will be at the Berkshire Athenaeum on Saturday, December 2, 12 to 4 pm, to read and give away “Santa: My Life & Times”. There will also be buttons and bookmarks to take with you, and some nondenominational books to hand out too.

  • December Bebop with Poppy

    Witch Slapped 78 North Street, Pittsfield, MA, United States

    For Ages 2-6. Admission is $15 (grown ups are free with their child). Let’s bebop and play together! Recently crowned Majesty of the Berkshires, Poppy DaBubbly will provide opportunities for grown ups and their toddler to explore movement and language skills through dance, creative movement, echo songs, and more. Click here to register!