Pittsfield Holiday Events

Holiday Shindy 2025

Masonic Temple Association 13 Dec 2025

Mutts Gone Nuts: Santa Paws

The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201 14 Dec 2025

Taconic Theatre Craft Show

Taconic High School 13 Dec 2025

The Wizards of Winter at Colonial Theatre Pittsfield

Colonial Theatre Pittsfield 20 Dec 2025

A Christmas Story for $1

57 North St, Pittsfield, MA, United States, Massachusetts 01201 12 Dec 2025

Holiday Shindy 2025 Preview Shopping Hour

Masonic Temple 13 Dec 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

Sound Bath Meditation w/ Aimee

740 Williams Street, Pittsfield, MA, United States, Massachusetts 01201 26 Dec 2025

Holiday Open Studios

75 South Church St., 3rd floor, Studio 302, Pittsfield, MA 13 Dec 2025

Permanent Jewelry Pop-Up

Hot Plate Brewing Co. 20 Dec 2025

Christmas Eve Worship at Zion Lutheran Pittsfield

74 1st St, Pittsfield, MA, United States, Massachusetts 01201 24 Dec 2025

Holiday Stretch + Destress

740 Williams Street, Pittsfield, MA, United States, Massachusetts 01201 12 Dec 2025

Full Burn Nut Cracker @ Parkside !!

Parkside Restaurant 13 Dec 2025

The Light of Christmas, a holiday handbell concerrt

67 East Street, Pittsfield, MA, United States, Massachusetts 01201 14 Dec 2025

Saturnalia Party!

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

The Wizards Of Winter

Colonial Theatre - Pittsfield 19 Dec 2025

Jingle Barre Class

740 Williams Street, Pittsfield, MA, United States, Massachusetts 01201 24 Dec 2025

Soular Eclipse @ Pittsfield Council on Aging

Pittsfield Senior Center 19 Dec 2025

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

Benson's Pet Center (Pittsfield) 14 Dec 2025

Movie Afternoons | Screening of The Holiday

1 Wendell Avenue, Pittsfield, MA, United States, Massachusetts 01201 30 Dec 2025