Pittsfield Holiday Events

The Shining @ Holiday Inn

Holiday Inn & Suites Pittsfield-Berkshires by IHG 31 Oct 2026

The Polar Express with Santa Claus

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

The Polar Express for $1

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

Holiday Shindy 2026

Masonic Temple Association 12 Dec 2026

Taconic Theatre Craft Show

Taconic High School 12 Dec 2026