Pittsfield Festivals Events

The Little Mermen & The Princess Pals: Disney Sing Along

The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201 21 Nov 2026

Rev Tor's 30th Anniversary Jam

The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201 25 Sep 2026

Chili & Chowder Fest

16 Melville Street, Pittsfield, MA, United States, Massachusetts 01201 10 Jul 2026

Ivy League of Comedy Tour

The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201 12 Sep 2026

Bousquet Jazz + Blues Festival - Presented by Berkshires Jazz

101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201 8 Aug 2026

2nd Annual Youth Mental Health Wellness Fair

Pittsfield Farmers Market 11 Jul 2026

BCAC Community Day

The Common Park 16 Jul 2026

Back to the Garden 1969 - The Woodstock Experience

Colonial Theatre - Pittsfield 30 Aug 2026

Run for the Revolution 5K/10K/15K

Pittsfield State Forest 18 Oct 2026

Hootenanny 2026

Noble's Farm Stand And Flower Shop 25 Jul 2026

Little Bird Festival: Celebrating Lisa Mandeville, a Potluck and Open Song Circle

4-H Fairgrounds, Utility Drive, Pittsfield MA 25 Jul 2026

BEATTHESTREETS ALL STAR WEEKEND

Dorothy Amos Park 7 Aug 2026

SummerFest "Financial Tips for Investing in Your Child's Future"

5 Cheshire Road, Ste. 26 Pittsfield, MA 01201 6 Aug 2026