Entertainment Events and Things to do in Pittsfield, MA

Going fast
Hannah Montana Drag Brunch
Saturday at 11:00 AM
Albany · Common Roots Albany Outpost
Going fast
Hannah Montana Drag Brunch
Saturday at 11:00 AM
Albany · Common Roots Albany Outpost
Alison Arngrim: Confessions of a Prairie Bitch
Fri, May 8, 7:30 PM
West Stockbridge · The Foundry West Stockbridge
Alison Arngrim: Confessions of a Prairie Bitch
Fri, May 8, 7:30 PM
West Stockbridge · The Foundry West Stockbridge
Big Shrimp w/ Ryan Dempsey (of Twiddle) at Ophelia's
Sat, Apr 11, 9:00 PM
Albany · Ophelia's
Big Shrimp w/ Ryan Dempsey (of Twiddle) at Ophelia's
Sat, Apr 11, 9:00 PM
Albany · Ophelia's
DEATH and the THE FOOL: A Medieval Folly
Sun, Jun 21, 3:00 PM
West Stockbridge · The Foundry West Stockbridge
DEATH and the THE FOOL: A Medieval Folly
Sun, Jun 21, 3:00 PM
West Stockbridge · The Foundry West Stockbridge
Nutshell Playhouse: SpyJinks!
Sun, Jul 19, 3:00 PM
West Stockbridge · The Foundry West Stockbridge
Nutshell Playhouse: SpyJinks!
Sun, Jul 19, 3:00 PM
West Stockbridge · The Foundry West Stockbridge
¡Buen Provecho! Drag Brunch - Celebrating 3 Years!
Saturday at 11:00 AM
Holyoke · Fame Lounge
¡Buen Provecho! Drag Brunch - Celebrating 3 Years!
Saturday at 11:00 AM
Holyoke · Fame Lounge
Woody's Round Up 4/10/26 at Holyoke Media
Fri, Apr 10, 7:30 PM
Holyoke · Holyoke Media
Woody's Round Up 4/10/26 at Holyoke Media
Fri, Apr 10, 7:30 PM
Holyoke · Holyoke Media
Fairways of Halfmoon Comedy Show
Sat, Apr 11, 6:30 PM
Mechanicville · The Fairways of Halfmoon
Fairways of Halfmoon Comedy Show
Sat, Apr 11, 6:30 PM
Mechanicville · The Fairways of Halfmoon
Spring Through the Decades: Drag Brunch
Sun, Apr 26, 10:30 AM
Averill Park · Tighe's Bistro Americain
Spring Through the Decades: Drag Brunch
Sun, Apr 26, 10:30 AM
Averill Park · Tighe's Bistro Americain
Fourth of July Fire
Fri, Jul 3, 3:00 PM
Greenfield · Franklin County Fairgrounds
Fourth of July Fire
Fri, Jul 3, 3:00 PM
Greenfield · Franklin County Fairgrounds
Just added
Simpsons Steamed Hams - 30th Anniversary Event
Tue, Apr 14, 6:00 PM
Albany · Druthers Brewing Company
Just added
Simpsons Steamed Hams - 30th Anniversary Event
Tue, Apr 14, 6:00 PM
Albany · Druthers Brewing Company
MIDGETS WITH ATTITUDE "MIDGET MAYHEM TOUR" - Albany, NY
Sat, Jun 13, 9:00 PM
Albany · Empire Live
MIDGETS WITH ATTITUDE "MIDGET MAYHEM TOUR" - Albany, NY
Sat, Jun 13, 9:00 PM
Albany · Empire Live
A Lick & A Promise: Big Pride Hoedown 2026 in Hillsdale, NY.
Sat, Jun 13, 6:00 PM
Hillsdale · Taconic Ridge Farm
A Lick & A Promise: Big Pride Hoedown 2026 in Hillsdale, NY.
Sat, Jun 13, 6:00 PM
Hillsdale · Taconic Ridge Farm
Almost full
Ladies Night Out {Early Price} with Men in Motion -Brattleboro VT (21+)
Sat, Apr 18, 9:00 PM
Brattleboro · BAR 580
Almost full
Ladies Night Out {Early Price} with Men in Motion -Brattleboro VT (21+)
Sat, Apr 18, 9:00 PM
Brattleboro · BAR 580
I Miss Svint Festival.
Saturday at 11:00 AM
West Springfield · 235 Western Ave
I Miss Svint Festival.
Saturday at 11:00 AM
West Springfield · 235 Western Ave
Theatresports Semi Final 04/04/26
Sat, Apr 4, 8:00 PM
Schenectady · MOPCO:The Mopco Improv Theatre
Theatresports Semi Final 04/04/26
Sat, Apr 4, 8:00 PM
Schenectady · MOPCO:The Mopco Improv Theatre
Draglesque and Drink: Pride Kick Off Burlesque and Drag Show
Sun, May 31, 12:00 PM
Troy · Mean Max Brew Works Troy Taproom
Draglesque and Drink: Pride Kick Off Burlesque and Drag Show
Sun, May 31, 12:00 PM
Troy · Mean Max Brew Works Troy Taproom
Sizzle and Strut: Drag Brunch
Sun, May 3, 12:00 PM
Albany · Ophelia's
Sizzle and Strut: Drag Brunch
Sun, May 3, 12:00 PM
Albany · Ophelia's
Free Film Screening: The Tallest Dwarf
Saturday at 2:00 PM
Albany · Albany Public Library - Pine Hills Branch
Free Film Screening: The Tallest Dwarf
Saturday at 2:00 PM
Albany · Albany Public Library - Pine Hills Branch

Trends in Pittsfield

Explore more trends

Hannah Montana Drag Brunch

Hannah Montana Drag Brunch

Alison Arngrim: Confessions of a Prairie Bitch

Alison Arngrim: Confessions of a Prairie Bitch

Big Shrimp w/ Ryan Dempsey (of Twiddle) at Ophelia's

Big Shrimp w/ Ryan Dempsey (of Twiddle) at Ophelia's

DEATH and the THE FOOL: A Medieval Folly

DEATH and the THE FOOL: A Medieval Folly

Nutshell Playhouse: SpyJinks!

Nutshell Playhouse: SpyJinks!

¡Buen Provecho! Drag Brunch - Celebrating 3 Years!

¡Buen Provecho! Drag Brunch - Celebrating 3 Years!

Woody's Round Up 4/10/26 at Holyoke Media

Woody's Round Up 4/10/26 at Holyoke Media

Fairways of Halfmoon Comedy Show

Fairways of Halfmoon Comedy Show

Spring Through the Decades: Drag Brunch

Spring Through the Decades: Drag Brunch

Fourth of July Fire

Fourth of July Fire

Simpsons Steamed Hams - 30th Anniversary Event

Simpsons Steamed Hams - 30th Anniversary Event

MIDGETS WITH ATTITUDE "MIDGET MAYHEM TOUR" - Albany, NY

MIDGETS WITH ATTITUDE "MIDGET MAYHEM TOUR" - Albany, NY

A Lick & A Promise: Big Pride Hoedown 2026 in Hillsdale, NY.

A Lick & A Promise: Big Pride Hoedown 2026 in Hillsdale, NY.

Ladies Night Out {Early Price} with Men in Motion -Brattleboro VT (21+)

Ladies Night Out {Early Price} with Men in Motion -Brattleboro VT (21+)

I Miss Svint Festival.

I Miss Svint Festival.

Theatresports Semi Final 04/04/26

Theatresports Semi Final 04/04/26

Draglesque and Drink: Pride Kick Off Burlesque and Drag Show

Draglesque and Drink: Pride Kick Off Burlesque and Drag Show

Sizzle and Strut: Drag Brunch

Sizzle and Strut: Drag Brunch

Free Film Screening: The Tallest Dwarf

Free Film Screening: The Tallest Dwarf

Things to do around Pittsfield

Trends in Pittsfield

1. Paint and sip

2. Dj lucas

3. Stand up comedy

4. Easter brunch

5. Angelz fury

6. Live music

7. Gay meetup

8. Groove for good

9. Events near me

10. Open mic

11. Speed dating

12. Craft fairs