Discover Comedy Events & Activities in Pittsfield, MA

Comedy Night at Thimble Island Brewing
Today at 7:30 PM
Thimble Island Brewing Company
Comedy Night at Thimble Island Brewing
Today at 7:30 PM
Thimble Island Brewing Company
Next Stop Comedy at Caius Farm Brewery! - Branford, CT
Sat, Mar 15, 7:00 PM
Caius Farm Brewery
Next Stop Comedy at Caius Farm Brewery! - Branford, CT
Sat, Mar 15, 7:00 PM
Caius Farm Brewery
Just added!
Todd Barry
Sat, May 31, 8:00 PM
Space Ballroom
Just added!
Todd Barry
Sat, May 31, 8:00 PM
Space Ballroom
Winter Fun Cupcake Class
Tomorrow at 10:00 AM
Oakholm Brewing Company
Winter Fun Cupcake Class
Tomorrow at 10:00 AM
Oakholm Brewing Company
Just added!
2025 Yale University | Joe Wong's Stand-Up Comedy Tour: Between Jobs
Sat, Apr 12, 6:00 PM
Davies Auditorium
Just added!
2025 Yale University | Joe Wong's Stand-Up Comedy Tour: Between Jobs
Sat, Apr 12, 6:00 PM
Davies Auditorium
Still On The Mountain X Woolen Mill Comedy Club - Comedy & Cocktails
Sun, Mar 2, 7:00 PM
Killington Distillery - Still on the Mountain
Still On The Mountain X Woolen Mill Comedy Club - Comedy & Cocktails
Sun, Mar 2, 7:00 PM
Killington Distillery - Still on the Mountain
Thirdspace Comedy night
Today at 8:00 PM
410 Blake Street, New Haven, CT, USA
Thirdspace Comedy night
Today at 8:00 PM
410 Blake Street, New Haven, CT, USA
Little Mania Wrestling: Mini Champions, Massive Thrills! Danbury, CT
Mon, Jun 16, 7:30 PM
The Roxy
Little Mania Wrestling: Mini Champions, Massive Thrills! Danbury, CT
Mon, Jun 16, 7:30 PM
The Roxy
Stand Up Comedy At Woolen Mill Comedy Club With Headliner Mike Celona!
Sat, Apr 12, 8:00 PM
Woolen Mill Comedy Club
Stand Up Comedy At Woolen Mill Comedy Club With Headliner Mike Celona!
Sat, Apr 12, 8:00 PM
Woolen Mill Comedy Club
R&B Comedy Showcase
Sat, May 10, 7:00 PM
Norwalk City Concert Hall
R&B Comedy Showcase
Sat, May 10, 7:00 PM
Norwalk City Concert Hall
Stand Up Comedy At Woolen Mill Comedy Club With Headliner Max Higgins!
Sat, Apr 19, 8:00 PM
Woolen Mill Comedy Club
Stand Up Comedy At Woolen Mill Comedy Club With Headliner Max Higgins!
Sat, Apr 19, 8:00 PM
Woolen Mill Comedy Club
Urban Culture
Sun, Mar 16, 4:00 PM + 17 more
60 Connolly Pkwy
Urban Culture
Sun, Mar 16, 4:00 PM + 17 more
60 Connolly Pkwy
Hypnotist Joe DiVito voted as #1 comic, a Family-Friendly Event
Sat, Mar 29, 7:30 PM
North Middlesex Regional High School
Hypnotist Joe DiVito voted as #1 comic, a Family-Friendly Event
Sat, Mar 29, 7:30 PM
North Middlesex Regional High School
Just added!
Iridescent Falls - Paint and Sip by Classpop!™
Thu, Mar 20, 7:00 PM
Pinot's Palette Fishkill
Just added!
Iridescent Falls - Paint and Sip by Classpop!™
Thu, Mar 20, 7:00 PM
Pinot's Palette Fishkill
Comedy Night @ the VFW Westport
Fri, Apr 11, 8:00 PM
Veterans of Foreign Wars
Comedy Night @ the VFW Westport
Fri, Apr 11, 8:00 PM
Veterans of Foreign Wars
Danbury, CT - Little Mania Midget Wrestling @ The Roxy
Mon, Jun 16, 7:30 PM
40 Mill Plain Rd
Danbury, CT - Little Mania Midget Wrestling @ The Roxy
Mon, Jun 16, 7:30 PM
40 Mill Plain Rd
Dirty Dixie’s Drag Brunch - New Date due to Weather
Sun, Mar 23, 12:00 PM
Grand St. Tavern
Dirty Dixie’s Drag Brunch - New Date due to Weather
Sun, Mar 23, 12:00 PM
Grand St. Tavern
The Princess Bride: An Inconceivable Evening with Cary Elwes
Sat, Apr 5, 8:00 PM
College Street Music Hall
The Princess Bride: An Inconceivable Evening with Cary Elwes
Sat, Apr 5, 8:00 PM
College Street Music Hall
Steve Hofstetter
Sat, Oct 4, 7:00 PM
Space Ballroom
Steve Hofstetter
Sat, Oct 4, 7:00 PM
Space Ballroom
Just added!
Doug Stanhope & Andy Andrist
Fri, Oct 24, 7:00 PM
Space Ballroom
Just added!
Doug Stanhope & Andy Andrist
Fri, Oct 24, 7:00 PM
Space Ballroom

Comedy Night at Thimble Island Brewing

Comedy Night at Thimble Island Brewing

Next Stop Comedy at Caius Farm Brewery! - Branford, CT

Next Stop Comedy at Caius Farm Brewery! - Branford, CT

Todd Barry

Todd Barry

Winter Fun Cupcake Class

Winter Fun Cupcake Class

2025 Yale University | Joe Wong's Stand-Up Comedy Tour: Between Jobs

2025 Yale University | Joe Wong's Stand-Up Comedy Tour: Between Jobs

Still On The Mountain X Woolen Mill Comedy Club - Comedy & Cocktails

Still On The Mountain X Woolen Mill Comedy Club - Comedy & Cocktails

Thirdspace Comedy night

Thirdspace Comedy night

Little Mania Wrestling: Mini Champions, Massive Thrills! Danbury, CT

Little Mania Wrestling: Mini Champions, Massive Thrills! Danbury, CT

Stand Up Comedy At Woolen Mill Comedy Club With Headliner Mike Celona!

Stand Up Comedy At Woolen Mill Comedy Club With Headliner Mike Celona!

R&B Comedy Showcase

R&B Comedy Showcase

Stand Up Comedy At Woolen Mill Comedy Club With Headliner Max Higgins!

Stand Up Comedy At Woolen Mill Comedy Club With Headliner Max Higgins!

Urban Culture

Urban Culture

Hypnotist Joe DiVito voted as #1 comic, a Family-Friendly Event

Hypnotist Joe DiVito voted as #1 comic, a Family-Friendly Event

Iridescent Falls - Paint and Sip by Classpop!™

Iridescent Falls - Paint and Sip by Classpop!™

Comedy Night @ the VFW Westport

Comedy Night @ the VFW Westport

Danbury, CT - Little Mania Midget Wrestling @ The Roxy

Danbury, CT - Little Mania Midget Wrestling @ The Roxy

Dirty Dixie’s Drag Brunch - New Date due to Weather

Dirty Dixie’s Drag Brunch - New Date due to Weather

The Princess Bride: An Inconceivable Evening with Cary Elwes

The Princess Bride: An Inconceivable Evening with Cary Elwes

Steve Hofstetter

Steve Hofstetter

Doug Stanhope & Andy Andrist

Doug Stanhope & Andy Andrist

Things to do around Pittsfield

Trends in Pittsfield

1. Valentines day events

2. Stand up comedy

3. Singles events

4. Paint and sip

5. Live music

6. Craft fairs

7. Rewritten

8. Teens

9. Bingo

10. Valentines day dinner

11. Murder mystery dinners

12. February 2025