Upcoming Live Music Events

Aquanett LIVE at Proprietor's Lodge

 The Proprietor's Lodge - Lakefront Events, Dining & Venue 14 Mar 2026
MUSIC

10 by Satch: The Music of Louis Armstrong

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

The Lovin' Spoonful in Pittsfield

 The Colonial Theatre 9 May 2026
ART

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Upcoming Food & Drinks Events

Community Dinner with seeing rainbows

 175 Wendell Ave, Pittsfield, MA 01201-6927, United States 21 Feb 2026
FOOD-DRINKS

Winter Reading Olympics Read-In

 Berkshire Athenaeum 20 Feb 2026

SHYNE RETURNS TO Tavern at The A!!!!

 Tavern at the A 7 Mar 2026
PARTIES

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Upcoming Festivals Events

3rd Annual Winter Festival at Clapp Park

 Clapp Park 16 Feb 2026
FESTIVALS

Shredfest Rewind: 80's Day + Bank Slalom

 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201 7 Mar 2026
SPORTS

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

 Clock Tower Artists' Studios and Gallery 17 Feb 2026
ART USD 23

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Upcoming Valentine's Day Events

Red & White Valentines Day Party 🔥

Tavern at the A 14 Feb 2026
VALENTINES-DAY

DJ on the Deck Après Ski Party

 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201 14 Feb 2026
PARTIES

Sanctum Gallery Grand Opening (Invitation for Love)

 148 North St Pittsfield Ma 01201 14 Feb 2026
MEETUPS

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Upcoming Comedy Events

Kristin Key: The Camp Kristin Tour

 The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201 27 Mar 2026
COMEDY

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

 Methuselah Bar and Lounge 16 Feb 2026
MUSIC FREE

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

 Pittsfield 30 Oct 2025
ART FREE

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Upcoming Galentines Day Events

Galentine's Day at the Barre

 740 Williams Street, Pittsfield, MA, United States, Massachusetts 01201 12 Feb 2026
GALENTINES-DAY

Anti-Valentine's Day Party | Teen Programming

 1 Wendell Avenue, Pittsfield, MA, United States, Massachusetts 01201 13 Feb 2026
PARTIES

Paint Your Bestie GALENTINE

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

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Trending Events in Pittsfield

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

 Berkshire Community College 16 Feb 2026
ART

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

 Methuselah Bar and Lounge 17 Feb 2026
MARDI-GRAS

Bay State Games - Alpine Skiing

 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201 15 Mar 2026
SPORTS

‘90s Nation: Alternative Rock

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

Days of Play at Berkshire Community College

 Berkshire Community College 17 Feb 2026
TRIPS-ADVENTURES

Beyond The Wall Performs Dark Side of the Moon

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

Bianchi/Barbarotta Foundation 12th Annual Beer Tasting

 Berkshire Hills Country Club 28 Feb 2026
SPORTS

3rd Annual Night of Dreams Gala 2026

 Berkshire Hills Country Club 8 May 2026
MUSIC

Day of Play with the Berkshire Museum

 Berkshire Athenaeum 21 Feb 2026

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

 Clock Tower Business Park 7 Feb 2026
ART

Paint 'n Sip

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

Dark Side of the Moon performed by Beyond the Wall

 Colonial Theatre 14 Mar 2026
CONCERTS

Four Sticks: The Music of Led Zeppelin

 111 South St., Pittsfield, MA, United States, Massachusetts 01201 4 Apr 2026
MUSIC

Après Ski Party at Bousquet

 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201 21 Feb 2026
PARTIES

The Flannel Kings DEBUT at The Proprietor’s Lodge!

 The Proprietor's Lodge - Lakefront Events, Dining & Venue 7 Mar 2026
PARTIES

More things to do in Pittsfield

Live Music
Food & Drinks
Festivals
Valentine's Day
Comedy
Galentines Day
St. Patrick's Day
Mardi Gras
Presidents Day
Carnivals
Pop-Ups