Happening Next

Pittsfield Holiday Events

Holiday events Happening Next in Pittsfield, MA

Christmas Dreamland

Main Location: 475 Tyler St, Pittsfield, MA 12 Dec 2026
TRIPS-ADVENTURES

The Polar Express with Santa Claus

 57 North St, Pittsfield, MA, United States, Massachusetts 01201 12 Dec 2026
ART

The Light Before Christmas with Trek Track Collective

 The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201 28 Nov 2026
MUSIC

The Polar Express for $1

 57 North St, Pittsfield, MA, United States, Massachusetts 01201 11 Dec 2026
ART

Holiday Shindy 2026

 Masonic Temple Association 12 Dec 2026
HOLIDAY

Santa Brunch

Berkshire Hills Country Club, Benedict Road, Pittsfield, MA, USA 19 Dec 2026
KIDS

Yoga Dance: Move, Release & Reconnect ✨

 55 North St, Pittsfield, MA, United States, Massachusetts 01201 11 Nov 2026
HEALTH-WELLNESS

The Not Gala

 Pittsfield, Massachusetts 7 Nov 2026
CHARITIES

Prepare Him Room

 172 Hubbard Ave, Pittsfield, MA, United States, Massachusetts 01201 14 Nov 2026
CALENDAR

Taconic Theatre Craft Show

 Taconic High School 12 Dec 2026
ART

WREATH ART AUCTION to benefit The Pittsfield Community Food Pantry

 Lichtenstein Center for the Arts 2 Dec 2026
ART

Holiday Dinner

 Zucchini's 1331 North St, Pittsfield, MA 01201 5 Dec 2026
HOLIDAY