Upcoming Pittsfield Events

Check out what's happening all around Pittsfield, MA

Bay State Games - Alpine Skiing

 Sun, 15 Mar at 08:30 am 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201

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

Days of Play at Berkshire Community College

 Tue, 17 Feb at 10:30 am Berkshire Community College

‘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

3rd Annual Winter Festival at Clapp Park

 Mon, 16 Feb at 10:00 am Clapp Park

Shredfest Rewind: 80's Day + Bank Slalom

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

Bianchi/Barbarotta Foundation 12th Annual Beer Tasting

 Sat, 28 Feb at 06:00 pm Berkshire Hills Country Club

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

Day of Play with the Berkshire Museum

 Sat, 21 Feb at 10:30 am Berkshire Athenaeum

3rd Annual Night of Dreams Gala 2026

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

The Little Mermen & The Princess Pals: Disney Sing Along

 Fri, 20 Feb at 07:00 pm The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201

Full Burn Slides Into The A !!

 Sat, 21 Feb at 08:00 pm Tavern at the A

Youth Group Paint & Sip

Sat, 21 Feb at 06:00 pm 172 Hubbard Ave, Pittsfield, MA, United States, Massachusetts 01201

Cosmic Bowling- STRIKE OUT GLIOBLASTOMA!

 Sat, 07 Mar at 06:00 pm K&M Bowling

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

Paint 'n Sip

 Fri, 20 Feb at 06:00 pm 444 North St, 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

AQUANETT

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

Après Ski Party at Bousquet

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

Women's Chili & Potato Bar

 Sat, 28 Feb at 05:30 pm 172 Hubbard Ave, Pittsfield, MA, United States, Massachusetts 01201

10x10 Real Art Party 2026

 Thu, 19 Feb at 06:00 pm Clock Tower Artists

Deal Me In - Casino Night to Benefit The Christian Center

 Fri, 10 Apr at 06:00 pm 193 Robbins Ave, Pittsfield, MA

🍞 Dine & Donate: Support Families Like Ours at Panera! 🍞

 Sat, 14 Feb at 04:00 pm Panera Bread, 635 Merrill Road, Pittsfield, MA 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

Galentine's Day at the Barre

 Thu, 12 Feb at 05:45 pm 740 Williams Street, Pittsfield, MA, United States, Massachusetts 01201

The Lovin’ Spoonful

 Sat, 09 May at 07:30 pm The Colonial Theatre - 111 South St., 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

JOY IS RESIST DANCE

 Wed, 25 Feb at 06:00 pm W A N D E R Berkshires

Valentine’s Day ❤️🩷❤️

 Sat, 14 Feb at 11:00 am 490 Pitsfield Rd, Lenox, MA

Sanctum Gallery Grand Opening (Invitation for Love)

 Sat, 14 Feb at 01:00 pm 148 North St Pittsfield Ma 01201

I’m Going To Graceland

 Fri, 01 May at 07:30 pm The Colonial Theatre - 111 South St., 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

Cardio Kickboxing (8-week series: Jan. 4th - Feb. 22nd)

 Sun, 15 Feb at 09:15 am 55 North 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

Community Dinner with seeing rainbows

 Sat, 21 Feb at 07:00 pm 175 Wendell Ave, Pittsfield, MA 01201-6927, United States

Rock & Bowl Fundraiser for Pittsfield Community Food Pantry

 Sat, 18 Apr at 05:00 pm New Moon Lodge

RAD Women's Self Defense Training Certification

 Sat, 21 Feb at 10:00 am Allendale Shopping Center, 5 Cheshire Rd , Suite 119 , Pittsfield,MA 01201, Pittsfield, MA, United States, Massachusetts 01201

Dale Derby Cardboard Box Race

 Sun, 08 Mar at 11:00 am 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201

A Salute to the American Soldier a Military Musical- Presented by Wayne Soares

 Sat, 28 Feb at 06:00 pm The Proprietor's Lodge - Lakefront Events, Dining & Venue

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

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

Beginner’s Flower Cupcake Decorating | Community Education Workshop

 Sat, 07 Mar at 11:00 am 1350 West St, Pittsfield, MA, United States, Massachusetts 01201

Gateway Fiber Free Bowling Night

Fri, 27 Feb at 07:00 pm K&M Bowling

SPINDLE (music bingo) w/ DJ Pup Daddy - Songs of the 2000s

 Thu, 26 Mar 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

Bass Large Mouth Bass/Small Mouth Bass 101 w/Spencer Cookson

Mon, 23 Feb at 06:30 pm Patrick's Pub

Paint & Sip ( Sunshine Daisies Porch Leaner)

 Wed, 11 Mar at 06:00 pm Proprietor's Lodge USD 50

Queer Crafting @WANDER hosted by Rainbow Seniors

 Sat, 28 Feb WANDER Berkshires Free

Queer Crafting @WANDER hosted by Rainbow Seniors

 Sat, 14 Feb WANDER Berkshires Free

Q-MoB Board/Leadership Team Meeting (Pittsfield, MA)

 Sun, 22 Feb at 03:00 pm Downtown Pittsfield Free

Planning Team Berkshire Pride Art Exhibit @Berkshire Athenaeum Pittsfield

 Thu, 12 Feb at 06:30 pm Berkshire Athenaeum, Pittsfield's Public Library Free

Ballet Foundations (8-Week Series: Jan. 5th - Feb. 23rd)

 Mon, 16 Feb at 04:15 pm 55 North St, Pittsfield, MA, United States, Massachusetts 01201

Free Ski Demo Day

 Mon, 16 Feb at 09:00 am 101 Dan Fox Dr, Pittsfield, MA, United States, Massachusetts 01201

10x10 Festival: Winter Tree Identification Walk at Springside Park

 Sat, 14 Feb at 10:00 am Springside Park

Beaver Detectives at Canoe Meadows

 Mon, 16 Feb at 04:00 pm Canoe Meadows Wildlife Sanctuary

Quick & Easy Dinners | Community Education Workshop

 Tue, 10 Mar at 05:30 pm 1350 West 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

Winter Reading Olympics Read-In

 Fri, 20 Feb at 10:00 am Berkshire Athenaeum

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

Bring Your Own Vinyl w/ DJ Pup Daddy

 Fri, 27 Feb at 07:00 pm Hot Plate Brewing Co.

Monday Mahjong Group | All Ages Programming

Mon, 16 Feb at 12:30 pm 1 Wendell Avenue, Pittsfield, MA, United States, Massachusetts 01201

Open Sanctuary

Wed, 18 Feb at 03:00 pm 74 1st St, Pittsfield, MA, United States, Massachusetts 01201

Paint & Sip

 Fri, 27 Mar at 06:00 pm Tavern At The A USD 45

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

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

 Sat, 21 Feb at 02:00 pm Lenox Memorial Middle and High School

Musical Theatre Audition Workshop for Youth

 Sat, 28 Feb at 01:00 pm Barrington Stage Company Ed. Department

Cognitive Behavioral Therapy for Suicide Prevention (CBT-SP)

 Fri, 10 Apr at 08:00 am Berkshire Innovation Center, Woodlawn Avenue, Pittsfield, MA, USA USD 35

Making Way for Wildlife: Reconnecting Nature Across Our Landscapes

 Sat, 11 Apr at 09:30 am Berkshire Community College Free

SheJumps | WILD SKILLS Junior Ski Patrol | MA

 Sat, 07 Mar at 08:30 am 101 Dan Fox Dr USD 0 to 50

Monthly Community Potluck

 Thu, 05 Mar at 04:00 pm W A N D E R Berkshires

Jazz Vespers

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

"STRIKING OUT CANCER IN THE BERKSHIRES "!! /Joe Adee & The Lug Nuts

Sat, 21 Feb at 07:00 pm Proprietor's Lodge

Berkshire Book Con: A Celebration of Reading & Writing

 Sat, 18 Apr at 12:30 pm 1 Wendell Avenue, Pittsfield, MA, United States, Massachusetts 01201

BR&B returns to Bei Tempi for Valentine’s Day

 Sat, 14 Feb at 08:00 pm Bei Tempi - Good Times

XWA PRO WRESTLING

 Sat, 21 Mar at 05:00 pm Masonic Temple Association

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

 Mon, 23 Feb at 06:00 pm The Colonial Theatre - 111 South St., Pittsfield, MA, United States, Massachusetts 01201

All Over the Map Returns to Tavern at the A!!!!

Fri, 13 Mar at 06:00 pm Tavern at the A

Queer Crafting @ Wander

 Sat, 28 Mar at 12:30 pm W A N D E R Berkshires

Paint & Sip

 Wed, 08 Apr at 06:00 pm Proprietor's Lodge USD 50

Pretty Paws Nail Clinic

 Sat, 09 May at 09:00 am Benson's Pet Center (Pittsfield)

Open House

 Tue, 24 Feb at 05:30 pm 74 1st St, Pittsfield, MA, United States, Massachusetts 01201

Candlelight Yoga with Taylor

 Fri, 27 Feb at 06:00 pm On Pointe Barre & Fitness Studio

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

 Sun, 22 Feb at 12:30 pm Downtown Pittsfield Free

Register for KidsAct! Spring Break Camp

 Mon, 20 Apr at 09:00 am 122 North Street, Pittsfield, MA, United States, Massachusetts 01201

Paint & Sip

 Sat, 11 Apr at 01:00 pm Tavern At The A USD 50

Breaking Out of the Mid-Winter Blues IV

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

BERK12 Education Community Convening

 Fri, 20 Mar at 08:30 am Berkshire Community College Free

Playwriting Class with Jessica Provenz

 Wed, 04 Mar at 02:00 pm WANDER Berkshires Free

Anti-Valentine's Day Party | Teen Programming

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

10 x 10 Book Fair and Author signing

 Sat, 14 Feb at 02:00 pm Hot Plate Brewing Co.

Self-Love Sound Bath Meditation w/ Aimee

 Fri, 20 Feb at 06:00 pm 740 Williams Street, Pittsfield, MA, United States, Massachusetts 01201

THE COLLAB Artist Showcase: Live, Loud & Local

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