Windsor Comedy Events

Kenny Vs Spenny Live In Windsor

RockStar Music Hall 12 Dec 2025

Windsor Comedy Club Proshow

468 Erie St E 12 Dec 2025

The Vaudevillianaires' Krampus Ball with Posh Toboggan

Meteor 20 Dec 2025

The 12 Lies of Christmas - A Holiday Magic Experience

1477 Wyandotte St E, Windsor, ON, Canada, Ontario N9A 3L1 12 Dec 2025

Laughing at Lionshead holiday edition 2025!

Lion's Head Tavern 12 Dec 2025

Hershawn Arora LIVE Comedy At Tipsy Toucan (Feb 21st)

The Tipsy Toucan 21 Feb 2026

The Jimmy Show-Christmas Comedy Charity LIVE At The Tipsy Toucan (Dec 20th)

The Tipsy Toucan 20 Dec 2025

Tim Reaburn's Heckle Show at Windsor Comedy Club vol.1

89 university ave west, Windsor, ON, Canada, Ontario 30 Dec 2025

Brutal Comedy Tour LIVE at The Tipsy Toucan (January 17)

The Tipsy Toucan 17 Jan 2026

Canada's Drag Race Episode 5 Viewing Party

The Man's Shop & Barbershop Bar 18 Dec 2025

Bo Johnson Live in Windsor

Meteor 14 Dec 2025

The Brutal Comedy Tour - Windsor ON

The Tipsy Toucan - Public House 17 Jan 2026

A Riverfront Double Feature!

Paulin Memorial Presbyterian Church 30 Jan 2026

Rose City Comedy Festival - Capitol Headline Show

Capitol Theatre Windsor 31 Jan 2026

Roast of Windsor - Rose City Comedy Festival @ The Capitol Theatre

121 University Avenue West,Windsor,N9A 4K7,CA 31 Jan 2026

Round 8: Funniest comedian in Windsor Competition - a part of The Brewing For Comedy Festival III

89 university ave west, Windsor, ON, Canada, Ontario 31 Dec 2025

Hot A Heck Comedy Tour - Windsor

Meteor 19 Dec 2025

Canadian Famous Comedy Tour LIVE at The Tipsy Toucan (December 13)

The Tipsy Toucan 13 Dec 2025

Uncle Lazer

Windsor Laughs 18 Jan 2026

Leo Dufour LIVE Comedy At Tipsy Toucan (January 3rd)

The Tipsy Toucan 3 Jan 2026

Armin Arbabi LIVE Comedy At Tipsy Toucan (December 19-20th)

The Tipsy Toucan 19 Dec 2025

Rob Mailloux LIVE Comedy At Tipsy Toucan (December 26-27th)

The Tipsy Toucan 26 Dec 2025

Andrew Santino at The Colosseum at Caesars Windsor

The Colosseum at Caesars Windsor 16 Jan 2026

Dave Merheje-Christmas Edition LIVE Comedy At Tipsy Toucan (December 27th)

The Tipsy Toucan 27 Dec 2025

Danger Cats Comedy Live in Windsor March 13 🔥

The Cherry Rock Lounge 13 Mar 2026

Culturally Inappropriate | STAND UP COMEDY TOUR | 2025

Meteor 24 Jan 2026

One Helluva Drag Show

Chapter Two Brewing Company 17 Jan 2026

Steve-O Crash & Burn Tour Windsor ON

The Chrysler Theatre 12 Feb 2026

Fledermaus! A Champagne Masquerade

Capitol Theatre Windsor 8 Jan 2026

Clean Comedian Jim McCue "The Circuit" 53

1570 Marentette Ave, Windsor, ON N8X 4E3, Canada 15 Jan 2026

The Dirty Show at Windsor Comedy Club

89 university ave west, Windsor, ON, Canada, Ontario 30 Dec 2025

Pasta and Punches for Sam Canty

East Windsor 14 Dec 2025

Snowed in Comedy Tour- Windsor

Capitol Theatre Windsor 7 Apr 2026

Improv Drop In Event

2345 Edna St, Windsor, ON N8Y 4W8, Canada 3 Feb 2026

SCHOOL PERFORMANCE: A Riverfront Double Feature!

3200 Woodland Ave, Windsor, ON N9E 1Z5, Canada 30 Jan 2026

Late Show Presented by Windsor Comedy Club

Craft Heads Brewing Company 4 Oct 2024

Windsor Comedy Club Presents Brewing For Comedy Tuesdays

468 Erie St E 9 Jan 2024

Hannah Berner

The Colosseum at Caesars Windsor 20 Feb 2026