Entertainment events in Pittsfield

Check out happening entertainment events all around Pittsfield, MA

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

 Mon, 16 Feb at 11:00 am Berkshire Community College

Beyond The Wall Performs Dark Side of the Moon

 Sat, 14 Mar at 07:30 pm The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201

Aquanett LIVE at Proprietor's Lodge

 Sat, 14 Mar at 08:00 pm The Proprietor's Lodge - Lakefront Events, Dining & Venue

‘90s Nation: Alternative Rock

 Sat, 21 Feb at 07:30 pm The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201

Kristin Key: The Camp Kristin Tour

 Fri, 27 Mar at 07:30 pm The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201

10 by Satch: The Music of Louis Armstrong

 Fri, 20 Feb at 07:30 pm The Proprietor's Lodge - Lakefront Events, Dining & Venue

The Lovin' Spoonful in Pittsfield

 Sat, 09 May at 07:00 pm The Colonial Theatre

Shredfest Rewind: 80's Day + Bank Slalom

 Sat, 07 Mar at 12:00 pm 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201

Red & White Valentines Day Party 🔥

Sat, 14 Feb at 09:00 pm Tavern at the A

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

 Tue, 17 Feb at 06:00 pm Clock Tower Artists' Studios and Gallery USD 23

3rd Annual Night of Dreams Gala 2026

 Fri, 08 May at 06:00 pm Berkshire Hills Country Club

Dark Side of the Moon performed by Beyond the Wall

 Sat, 14 Mar at 07:30 pm Colonial Theatre

DJ on the Deck Après Ski Party

 Sat, 14 Feb at 12:00 pm 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201

Four Sticks: The Music of Led Zeppelin

 Sat, 04 Apr at 07:30 pm 111 South St., Pittsfield, MA, United States, Massachusetts 01201

Vinyl Night w/ DJ Pup Daddy - Mardi Gras 2026 @ 45 RPM

 Tue, 17 Feb at 07:00 pm Methuselah Bar and Lounge

Après Ski Party at Bousquet

 Sat, 21 Feb at 12:00 pm 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201

The Flannel Kings DEBUT at The Proprietor’s Lodge!

 Sat, 07 Mar at 08:00 pm The Proprietor's Lodge - Lakefront Events, Dining & Venue

DJ on the Deck Après Ski Party

 Sat, 14 Mar at 12:00 pm 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201

Rev Tor’s 30th Anniversary Jam

 Sat, 28 Mar at 07:30 pm The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201

SPINDLE (music bingo) w/ DJ Pup Daddy - Golden Age of Hip Hop

 Thu, 26 Feb at 07:00 pm Thistle and Mirth

Yacht Lobsters

 Sat, 30 May at 07:30 pm The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201

NEW Queer Live Jazz Valentine Mondays @ Methuselah (Pittsfield, MA)

 Mon, 16 Feb at 06:00 pm Methuselah Bar and Lounge Free

Little Lies: A Tribute to Fleetwood Mac

 Fri, 10 Apr at 07:30 pm The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201

Live Music with Jack Waldheim

 Mon, 16 Feb at 12:00 pm 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201

SHYNE RETURNS TO Tavern at The A!!!!

 Sat, 07 Mar at 08:00 pm Tavern at the A

SKI-BR Day w/ Pabst Blue Ribbon

 Sat, 14 Mar at 12:00 pm 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201

Jazz Vespers

 Wed, 04 Mar at 06:00 pm 74 1st St, Pittsfield, MA, United States, Massachusetts 01201

Breaking Out of the Mid-Winter Blues IV

Sun, 22 Feb at 06:00 pm 75 North Street , Pittsfield, MA, United States, Massachusetts 01201

Anti-Valentine's Day Party | Teen Programming

 Fri, 13 Feb at 03:00 pm 1 Wendell Avenue, Pittsfield, MA, United States, Massachusetts 01201

THE COLLAB Artist Showcase: Live, Loud & Local

 Fri, 27 Feb at 06:30 pm WANDER Berkshires USD 13

Cards and Karaoke

 Sat, 21 Mar at 07:00 pm Country Club of Pittsfield - Berkshires USD 66 to 109

Musical Bingo

 Sat, 21 Feb at 03:00 pm 1 Meadow Ln USD 7 to 23

Bousquet Beach Party

 Tue, 17 Feb at 09:00 am 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201

All Over the Map Returns to Bei- Tempi!!!!

 Sat, 21 Feb at 09:00 pm Bei Tempi - Good Times

Movie Afternoons | Screening of Jurassic World Rebirth

 Tue, 17 Feb at 02:00 pm 1 Wendell Avenue, Pittsfield, MA, United States, Massachusetts 01201

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

 Thu, 30 Oct at 08:00 pm Pittsfield Free

Q-MoB Queer Music & Movement Class (Pittsfield, MA)

 Mon, 17 Nov at 05:30 pm Zion Lutheran Church (ELCA) Free

Karaoke Wednesdays!

 Wed, 04 Feb at 09:00 pm Methuselah Bar and Lounge