Comedy Events and Things to do in Pittsfield, MA

Lipstick and Laughter Comedy at Pub 34
Sat, May 30, 8:00 PM
West Haven · 439 Derby Ave
Lipstick and Laughter Comedy at Pub 34
Sat, May 30, 8:00 PM
West Haven · 439 Derby Ave
GOOD JUDY: Drag Show - West Hartford, CT
Sun, May 31, 12:30 PM
West Hartford · The Elbow Room
GOOD JUDY: Drag Show - West Hartford, CT
Sun, May 31, 12:30 PM
West Hartford · The Elbow Room
Going fast
Todd Barry: Extend All Courtesies Tour 2026
Fri, Jun 19, 8:00 PM
Cheshire · Counter Weight Brewing Co.
Going fast
Todd Barry: Extend All Courtesies Tour 2026
Fri, Jun 19, 8:00 PM
Cheshire · Counter Weight Brewing Co.
The Pattern Game: Weight Training for Premise-Based Improv w Josuel Rosario
Mon, Jun 1, 7:00 PM
Hartford · Sea Tea Improv Studios
The Pattern Game: Weight Training for Premise-Based Improv w Josuel Rosario
Mon, Jun 1, 7:00 PM
Hartford · Sea Tea Improv Studios
Yes, and...Another Round!
Thu, Jun 18, 7:00 PM + 3 more
Beacon · Happy Valley Arcade Bar
Yes, and...Another Round!
Thu, Jun 18, 7:00 PM + 3 more
Beacon · Happy Valley Arcade Bar
Something Rotten Jr. -Much Ado Cast
Sun, May 31, 1:00 PM
Poughkeepsie · James Earl Jones Theater
Something Rotten Jr. -Much Ado Cast
Sun, May 31, 1:00 PM
Poughkeepsie · James Earl Jones Theater
$h!tfaced Stand-up
Sat, Jun 13, 8:00 PM
Worcester · Hibernian Cultural Centre
$h!tfaced Stand-up
Sat, Jun 13, 8:00 PM
Worcester · Hibernian Cultural Centre
Comedy Night at Eli Cannon's Brewing Collective
Sat, Jun 13, 7:30 PM
Middletown · Eli Cannons Brewing Collective
Comedy Night at Eli Cannon's Brewing Collective
Sat, Jun 13, 7:30 PM
Middletown · Eli Cannons Brewing Collective
The 2nd Annual Lingerie Ball
Sat, Jun 6, 8:00 PM
Windsor Locks · The Venue
The 2nd Annual Lingerie Ball
Sat, Jun 6, 8:00 PM
Windsor Locks · The Venue
Straight Up Comedy with Ben Kirsch
Fri, May 29, 8:00 PM
New Haven · The Sandbox
Straight Up Comedy with Ben Kirsch
Fri, May 29, 8:00 PM
New Haven · The Sandbox
THE ROAST OF IAN BICK
Sat, Jun 27, 6:00 PM
Danbury · The Roxy
THE ROAST OF IAN BICK
Sat, Jun 27, 6:00 PM
Danbury · The Roxy
Sales end soon
Ballroom and Latin Kids Group Class
Wednesday at 4:30 PM + 32 more
Suffield · Fred Astaire Suffield
Sales end soon
Ballroom and Latin Kids Group Class
Wednesday at 4:30 PM + 32 more
Suffield · Fred Astaire Suffield
Something Rotten Jr. -All's Well Cast
Sat, May 30, 6:00 PM
Poughkeepsie · James Earl Jones Theater
Something Rotten Jr. -All's Well Cast
Sat, May 30, 6:00 PM
Poughkeepsie · James Earl Jones Theater
G Fi Di Streets
Sat, Aug 8, 8:00 PM
Springfield · 279 Main St
G Fi Di Streets
Sat, Aug 8, 8:00 PM
Springfield · 279 Main St
Lu Chekowsky, DON'T BUY WHAT I'M SELLING
Tue, Jun 16, 6:00 PM
Rhinebeck · Oblong Books [Rhinebeck]
Lu Chekowsky, DON'T BUY WHAT I'M SELLING
Tue, Jun 16, 6:00 PM
Rhinebeck · Oblong Books [Rhinebeck]
COMEDIAN, MAXWELL SHULTZ AT DARK HORSE
Fri, Jun 19, 8:00 PM
Southbridge · The Dark Horse
COMEDIAN, MAXWELL SHULTZ AT DARK HORSE
Fri, Jun 19, 8:00 PM
Southbridge · The Dark Horse
Pete Correale ~ Live at The Italian Society of Middletown
Sat, Oct 3, 5:30 PM
Middletown · Italian Society of Middletown
Pete Correale ~ Live at The Italian Society of Middletown
Sat, Oct 3, 5:30 PM
Middletown · Italian Society of Middletown
Counter Weight Presents Stand Up Comedy with Brendan Sagalow
Fri, Jul 17, 8:00 PM
Cheshire · Counter Weight Brewing Company
Counter Weight Presents Stand Up Comedy with Brendan Sagalow
Fri, Jul 17, 8:00 PM
Cheshire · Counter Weight Brewing Company
Next Stop Comedy at Black Hog Brewing! - Oxford, CT
Sat, Jun 13, 7:00 PM + 4 more
Oxford · Black Hog Brewing
Next Stop Comedy at Black Hog Brewing! - Oxford, CT
Sat, Jun 13, 7:00 PM + 4 more
Oxford · Black Hog Brewing
Paint Nite Brand Creative Events
Sun, Jun 21, 2:00 PM
New Salem · New Salem Cider
Paint Nite Brand Creative Events
Sun, Jun 21, 2:00 PM
New Salem · New Salem Cider

Trends in Pittsfield

Explore more trends

Lipstick and Laughter Comedy at Pub 34

Lipstick and Laughter Comedy at Pub 34

GOOD JUDY: Drag Show - West Hartford, CT

GOOD JUDY: Drag Show - West Hartford, CT

Todd Barry: Extend All Courtesies Tour 2026

Todd Barry: Extend All Courtesies Tour 2026

The Pattern Game: Weight Training for Premise-Based Improv w Josuel Rosario

The Pattern Game: Weight Training for Premise-Based Improv w Josuel Rosario

Yes, and...Another Round!

Yes, and...Another Round!

Something Rotten Jr. -Much Ado Cast

Something Rotten Jr. -Much Ado Cast

$h!tfaced Stand-up

$h!tfaced Stand-up

Comedy Night at Eli Cannon's Brewing Collective

Comedy Night at Eli Cannon's Brewing Collective

The 2nd Annual Lingerie Ball

The 2nd Annual Lingerie Ball

Straight Up Comedy with Ben Kirsch

Straight Up Comedy with Ben Kirsch

THE ROAST OF IAN BICK

THE ROAST OF IAN BICK

Ballroom and Latin Kids Group Class

Ballroom and Latin Kids Group Class

Something Rotten Jr. -All's Well Cast

Something Rotten Jr. -All's Well Cast

G Fi Di Streets

G Fi Di Streets

Lu Chekowsky, DON'T BUY WHAT I'M SELLING

Lu Chekowsky, DON'T BUY WHAT I'M SELLING

COMEDIAN, MAXWELL SHULTZ AT DARK HORSE

COMEDIAN, MAXWELL SHULTZ AT DARK HORSE

Pete Correale ~ Live at The Italian Society of Middletown

Pete Correale ~ Live at The Italian Society of Middletown

Counter Weight Presents Stand Up Comedy with Brendan Sagalow

Counter Weight Presents Stand Up Comedy with Brendan Sagalow

Next Stop Comedy at Black Hog Brewing! - Oxford, CT

Next Stop Comedy at Black Hog Brewing! - Oxford, CT

Paint Nite Brand Creative Events

Paint Nite Brand Creative Events

Things to do around Pittsfield

Trends in Pittsfield

1. Mothers day brunch

2. Stand up comedy

3. Singles events

4. Paint and sip

5. Lgbt

6. Speed dating

7. Events near me

8. Drag show

9. Open mic

10. Puppy yoga

11. Plant bingo lee ma

12. Bingo