Windsor Comedy Events

Steve-O Crash & Burn Tour Windsor ON

The Chrysler Theatre 12 Feb 2026

Hannah Berner

The Colosseum at Caesars Windsor 20 Feb 2026

Andrew Santino at The Colosseum at Caesars Windsor

The Colosseum at Caesars Windsor 16 Jan 2026

Parking Daniel Tosh

The Colosseum at Caesars Windsor 26 Jun 2026

Snowed in Comedy Tour- Windsor

Capitol Theatre Windsor 7 Apr 2026

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

The Tipsy Toucan 21 Feb 2026

The Brutal Comedy Tour - Windsor ON

The Tipsy Toucan - Public House 17 Jan 2026

Culturally Inappropriate | STAND UP COMEDY TOUR | 2025

Meteor 24 Jan 2026

Rose City Comedy Festival - Capitol Headline Show

Capitol Theatre Windsor 31 Jan 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

Montreal Comedy Takeover - Windsor

The Manchester Bar 17 Jan 2026

Andrew Santino: Live

The Colosseum at Caesars Windsor 16 Jan 2026

Hamoodi LIVE Comedy At Tipsy Toucan (Jan 24th)

The Tipsy Toucan 24 Jan 2026

SCHOOL PERFORMANCE: A Riverfront Double Feature!

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

One Helluva Drag Show

Chapter Two Brewing Company 17 Jan 2026

The Bridge: DETROIT Edition LIVE Comedy At Tipsy Toucan (Jan 10th)

The Tipsy Toucan 10 Jan 2026

MOLIÈRE’S TARTUFFE by Korda

2520 Seminole St, Windsor, ON, Canada, Ontario N8Y 1X4 30 Jan 2026

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

The Tipsy Toucan 28 Mar 2026

Comedy Night at Sidelines Sports Bar & Grill!

Sidelines Sports Bar & Grill 30 Jan 2026

Clean Comedian Jim McCue "The Circuit" 53

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

Improv Drop In Event

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

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

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

Two Asians One Mic | STAND UP COMEDY TOUR - 2026

Meteor 28 Mar 2026

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

The Tipsy Toucan 14 Mar 2026

A Riverfront Double Feature!

Paulin Memorial Presbyterian Church 30 Jan 2026

Bryan Hatt LIVE Comedy At Tipsy Toucan (Jan 31st)

The Tipsy Toucan 31 Jan 2026

Sandra Battaglini LIVE Comedy At Tipsy Toucan (Feb 7th)

The Tipsy Toucan 7 Feb 2026

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

The Tipsy Toucan 7 Mar 2026

Valentine's Day Comedy LIVE At Tipsy Toucan (Feb 14th)

The Tipsy Toucan 14 Feb 2026

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

The Tipsy Toucan 2 May 2026

Bryan O Gorgmon LIVE Comedy At Tipsy Toucan (Feb 28th)

The Tipsy Toucan 28 Feb 2026

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

The Tipsy Toucan 16 May 2026

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

The Tipsy Toucan 9 May 2026

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

The Tipsy Toucan 25 Apr 2026

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

The Tipsy Toucan 21 Mar 2026

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

The Tipsy Toucan 4 Apr 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

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

The Tipsy Toucan 11 Apr 2026

Weird Al Yankovic with Puddles Piddy Party

The Colosseum at Caesars Windsor 5 Jul 2026