Windsor Comedy Events

Daniel Tosh at The Colosseum at Caesars Windsor

The Colosseum at Caesars Windsor 25 Jun 2026

Weird Al Yankovic at The Colosseum at Caesars Windsor

The Colosseum at Caesars Windsor 4 Jul 2026

Daniel Tosh

The Colosseum At Caesars Windsor 24 Jun 2026

Parking Daniel Tosh

The Colosseum at Caesars Windsor 26 Jun 2026

Snowed in Comedy Tour- Windsor

Capitol Theatre Windsor 7 Apr 2026

Sobreviviendo Canadá - Comedia en Español - Windsor

Ciocco Café 21 Mar 2026

Mr.Lewin LIVE Comedy At Tipsy Toucan (Apr 11th)

The Tipsy Toucan 11 Apr 2026

The Supervillains of Comedy @ Villains Beastro

VillainsBeastro Windsor 28 Feb 2026

Jokes On Us Comedy Tour LIVE At Tipsy Toucan

The Tipsy Toucan 13 Mar 2026

Danger Cats Comedy Live in Windsor March 13 🔥

The Cherry Rock Lounge 13 Mar 2026

The Broadway Bunch: All Ages

Meteor 27 Feb 2026

Mark DeBonis LIVE Comedy At Tipsy Toucan (May 30th)

The Tipsy Toucan 30 May 2026

The Rule Of Three Comedy Competition

138 University Ave W 25 Apr 2026

Tyler Horvath LIVE Comedy At Tipsy Toucan (Apr 2nd)

The Tipsy Toucan 2 Apr 2026

Next Stop Comedy at The Lion's Head Tavern! - Windsor, ON

Lion's Head Tavern 27 Feb 2026

The Bridge: DETROIT Edition LIVE Comedy At Tipsy Toucan (Mar 14th)

The Tipsy Toucan 14 Mar 2026

WHH REUNION

Phog Lounge 6 Mar 2026

Tatiana Frank LIVE Comedy At Tipsy Toucan (Apr 24th)

The Tipsy Toucan 24 Apr 2026

Two Asians One Mic | STAND UP COMEDY TOUR - 2026

Meteor 28 Mar 2026

Night of Laughs: A Blue Collar Boxing and Windsor Comedy Club Collaboration

Blue Collar Boxing Academy 7 Mar 2026

Improv Rec League: Finals Night

The Shadowbox Theatre 28 Feb 2026

K*ll Tony, Kansei Yasuda "RESPECT!!" LIVE Comedy at Tipsy Toucan (Mar 28th)

The Tipsy Toucan 28 Mar 2026

Starlight Cabaret - A Tribute to Classic Drag

The Man's Shop & Barbershop Bar 7 Mar 2026

Jokes on Me Comedy Tour! Zahan Sigara and Miguel de la Barrera - Windsor

The Cherry Rock Lounge 6 Mar 2026

The Goat, or Who Is Sylvia? by Edward Albee

The Shadowbox Theatre 13 Mar 2026

The Mid-week (Midwest) Comedy Show at Sidelines!

Sidelines Sports Bar & Grill 26 Feb 2026

Erie St GastroPub & Lotus and Lattes - Street Festival

839 Erie Street East, Windsor, ON, Canada, Ontario N9A 3Y5 23 May 2026

Brad Wenzel LIVE Comedy At Tipsy Toucan (Mar 7th)

The Tipsy Toucan 7 Mar 2026

The Bridge: DETROIT Edition LIVE Comedy At Tipsy Toucan (May 9th)

The Tipsy Toucan 9 May 2026

Snowed in Comedy Tour at Capitol Theatre

Capitol Theatre 7 Apr 2026

Max Sheldrick LIVE Comedy At Tipsy Toucan (May 2nd)

The Tipsy Toucan 2 May 2026

Hannah Veldhoen LIVE Comedy At Tipsy Toucan (Mar 21st)

The Tipsy Toucan 21 Mar 2026

Hannah Lawrence LIVE Comedy At Tipsy Toucan (May 16th)

The Tipsy Toucan 16 May 2026

Michael Harrison LIVE Comedy At Tipsy Toucan (Apr 4th)

The Tipsy Toucan 4 Apr 2026

Parking Jim Gaffigan

The Colosseum at Caesars Windsor 7 Mar 2026

Leo Dufour LIVE Comedy At Tipsy Toucan (May 16th)

The Tipsy Toucan 16 May 2026

Hannah Lawrence LIVE Comedy At Tipsy Toucan (May 23rd)

The Tipsy Toucan 23 May 2026

Weird Al Yankovic with Puddles Piddy Party

The Colosseum at Caesars Windsor 5 Jul 2026

Na’im Ali and Dru Montana LIVE Comedy At Tipsy Toucan (Apr 25th)

The Tipsy Toucan 25 Apr 2026

Comedy At Walkerville Brewery

Walkerville Brewery 30 May 2026