Pittsfield Holiday Events

Holiday Shindy 2025

Masonic Temple Association 13 Dec 2025

The Wizards of Winter at Colonial Theatre Pittsfield

Colonial Theatre Pittsfield 20 Dec 2025

Taconic Theatre Craft Show

Taconic High School 13 Dec 2025

The Polar Express for $1

57 North St, Pittsfield, MA, United States, Massachusetts 01201 7 Nov 2025

Pride Night w/ DJ Pup Daddy - Mariah Vs. Kelly

Methuselah Bar and Lounge 4 Dec 2025

Elegant & Timeless Pittsfield Estate Sale Hosted By Berkshire Legacy

100 North Umberland Road, Pittsfield, MA, 01201 8 Nov 2025

The Polar Express with Santa Claus

57 North St, Pittsfield, MA, United States, Massachusetts 01201 8 Nov 2025

Santa's Workshop CRAFT FAIR AND HOLIDAY FUN!

255 Lebanon Ave, Pittsfield, MA 22 Nov 2025

An Evening of Holiday Jazz with Tim Jones

The Garage at The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201 13 Dec 2025

The Wizards of Winter return to the COLONIAL THEATER, PITTSFIELD MA

111 South St, Pittsfield, MA 01201-6174, United States 20 Dec 2025

WREATH ART AUCTION to benefit The Pittsfield Community Food Pantry

Lichtenstein Center for the Arts 6 Dec 2025

Cheers to the Holidays! 9th Annual Wreath Decorating Events!

325 Fort Hill Ave, Pittsfield, MA 25 Nov 2025

Saturnalia Party!

1 School Street, Pittsfield, MA, United States, Massachusetts 01201 19 Dec 2025

Festive Holiday Cooking | BCC Community Education Workshop

1350 West St, Pittsfield, MA, United States, Massachusetts 01201 10 Dec 2025

The Wizards Of Winter

Colonial Theatre - Pittsfield 19 Dec 2025

The Animal Support Project Fantasy Photos (Winter Fun & Holiday Theme)

Benson's Pet Center (Pittsfield) 14 Dec 2025

Thanksgiving Made Easy: A Hands-on Cooking Workshop | BCC Community Education Workshop

1350 West St, Pittsfield, MA, United States, Massachusetts 01201 12 Nov 2025

Cheers to the Holidays! 9th Annual Wreath Decorating Events!

325 Fort Hill Ave, Pittsfield, MA 9 Dec 2025