Entertainment events in Pittsfield

Check out happening entertainment events all around Pittsfield, MA

Magic Tree House: Showtime with Shakespeare

 Sat, 14 Feb at 02:00 pm The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201

‘90s Nation: Alternative Rock

 Sat, 21 Feb 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

Rev Tor’s 14th Annual Dead of Winter Jam

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

DJ on the Deck Après Ski Party

 Sun, 18 Jan at 12:00 pm 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201

The Lovin' Spoonful in Pittsfield

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

Benefit Fundraiser for Sally Tiska Rice

 Sun, 18 Jan at 03:00 pm The Proprietor's Lodge - Lakefront Events, Dining & Venue

Shredfest Rewind: 80's Day + Bank Slalom

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

3rd Annual Night of Dreams Gala 2026

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

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

Richmond Night at Balderdash

 Fri, 30 Jan at 06:00 pm Balderdash Cellars

The Refrigerators

 Fri, 06 Feb at 08:00 pm The Proprietor's Lodge - Lakefront Events, Dining & Venue

Four Sticks: The Music of Led Zeppelin

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

DJ on the Deck Après Ski Party

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

Even It Up comes to The Parkside!!

 Sat, 24 Jan at 09:00 pm Parkside Restaurant

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

Miracles for Miles Dance Marathon $1000 prize

 Sat, 07 Feb at 06:00 pm Berkshire Hills Country Club USD 29 to 55

2026 Brett Haas Racing Party

 Sat, 31 Jan at 05:00 pm Polish Falcon Club USD 10 to 25

Red & White Valentines Day Party 🔥

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

Basic Dinner Party | Community Education Workshop

 Tue, 03 Feb at 05:30 pm 1350 West St, Pittsfield, MA, United States, Massachusetts 01201

SKI-BR Day w/ Pabst Blue Ribbon

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

Movie Afternoons | Screening of National Treasure

 Tue, 20 Jan at 02:00 pm 1 Wendell Avenue, Pittsfield, MA, United States, Massachusetts 01201

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

 Sat, 07 Feb at 01:00 pm Clock Tower Business Park

PHS Boys Basketball Music Bingo (CASH PRIZES!!)

 Sat, 07 Feb at 07:00 pm Tavern at the A

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

Dark Side of the Moon performed by Beyond the Wall

 Sat, 14 Mar at 07:30 pm Colonial Theatre

The Animal Support Project Fantasy Photos (Valentine's Day / Mardi Gras Theme)

 Sun, 08 Feb at 12:00 pm Benson's Pet Center (Pittsfield)

Movie Afternoons | Screening of Mona Lisa Smile

 Tue, 27 Jan at 02:00 pm 1 Wendell Avenue, Pittsfield, MA, United States, Massachusetts 01201

Jazz Vespers

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

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

Yacht Lobsters

 Sat, 30 May at 07:30 pm The Colonial Theatre - 111 South 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

DJ on the Deck Après Ski Party

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

Puppi Pryde Presents: The Next Gen Showcase

 Tue, 10 Feb at 05:30 pm WANDER Berkshires USD 13 to 18

Protest Open Mic

 Wed, 11 Feb at 06:00 pm WanderPittsfield, 34 Depot St., Pittsfield, MA

A Vivaldi & Mozart Candlelight Experience In Pittsfield, MA🕯️Friday 30th January

 Fri, 30 Jan at 11:00 pm Zion Lutheran Church (ELCA)

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