Pittsfield Arts Events

Free President's Day Bubble Show at Berkshire Community College (11:00AM Show)

Berkshire Community College 16 Feb 2026

Beyond The Wall Performs Dark Side of the Moon

The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201 14 Mar 2026

10 by Satch: The Music of Louis Armstrong

The Proprietor's Lodge - Lakefront Events, Dining & Venue 20 Feb 2026

3rd Annual Winter Festival at Clapp Park

Clapp Park 16 Feb 2026

The Lovin' Spoonful in Pittsfield

The Colonial Theatre 9 May 2026

The Art Switch Benefit Auction Party for Roots Rising (10x10 Arts Festival)

Clock Tower Artists' Studios and Gallery 17 Feb 2026

10x10 Real Art Party (RAP) Call for Art and Drop-off

Clock Tower Business Park 7 Feb 2026

Paint 'n Sip

444 North St, Pittsfield, MA, United States, Massachusetts 01201 20 Feb 2026

Rev Tor’s 30th Anniversary Jam

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

Sanctum Gallery Grand Opening (Invitation for Love)

148 North St Pittsfield Ma 01201 14 Feb 2026

I’m Going To Graceland

The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201 1 May 2026

RAD Women's Self Defense Training Certification

Allendale Shopping Center, 5 Cheshire Rd , Suite 119 , Pittsfield,MA 01201, Pittsfield, MA, United States, Massachusetts 01201 21 Feb 2026

Beginner’s Flower Cupcake Decorating | Community Education Workshop

1350 West St, Pittsfield, MA, United States, Massachusetts 01201 7 Mar 2026

GESTURE

Unitarian Universalists of Pittsfield (Mass.) 10 Feb 2026

Queer Crafting @WANDER hosted by Rainbow Seniors

WANDER Berkshires 28 Feb 2026

Paint & Sip ( Sunshine Daisies Porch Leaner)

Proprietor's Lodge 11 Mar 2026

Planning Team Berkshire Pride Art Exhibit @Berkshire Athenaeum Pittsfield

Berkshire Athenaeum, Pittsfield's Public Library 12 Feb 2026

Paint & Sip

Tavern At The A 11 Apr 2026

10x10 Festival: Winter Tree Identification Walk at Springside Park

Springside Park 14 Feb 2026

Little Lies: A Tribute to Fleetwood Mac

The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201 10 Apr 2026

Paint & Sip

Tavern At The A 27 Mar 2026

Paint & Sip

Proprietor's Lodge 11 Feb 2026

29th Annual Winter Lecture: How's the Wow?

Lenox Memorial Middle and High School 21 Feb 2026

Berkshire Book Con: A Celebration of Reading & Writing

1 Wendell Avenue, Pittsfield, MA, United States, Massachusetts 01201 18 Apr 2026

Making Way for Wildlife: Reconnecting Nature Across Our Landscapes

Berkshire Community College 11 Apr 2026

Audition Call for BTG's Production of James & the Giant Peach JR.

The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201 23 Feb 2026

Paint & Sip

Proprietor's Lodge 8 Apr 2026

Q-MoB 3 Yr Anniv Community Potluck Brunch/Celebration (Pittsfield, MA)

Downtown Pittsfield 22 Feb 2026

Open House

74 1st St, Pittsfield, MA, United States, Massachusetts 01201 24 Feb 2026

10 x 10 Book Fair and Author signing

Hot Plate Brewing Co. 14 Feb 2026

THE COLLAB Artist Showcase: Live, Loud & Local

WANDER Berkshires 27 Feb 2026

Magic Tree House - Showtime with Shakespeare KIDS at Colonial Theatre Pittsfield

Colonial Theatre Pittsfield 14 Feb 2026

Paint Your Bestie GALENTINE

444 North St, Pittsfield, MA, United States, Massachusetts 01201 15 Feb 2026

Playwright Mentoring Project Show

36 Linden St, Pittsfield, MA 01201-3212, United States 31 Mar 2026

Playwright Mentoring Project Show

36 Linden St, Pittsfield, MA 01201-3212, United States 11 Apr 2026

Movie Afternoons | Screening of Jurassic World Rebirth

1 Wendell Avenue, Pittsfield, MA, United States, Massachusetts 01201 17 Feb 2026

Powerful Voices Open Mic Show - Live Music, Comedy, Poetry+ More!

Pittsfield 30 Oct 2025