Windsor Festivals Events

Art in the Park

Willistead Park 6 Jun 2026

Rose City Comedy Festival - Capitol Headline Show

Capitol Theatre Windsor 31 Jan 2026

S'mores & Cocoa Festival

400 Erie Street East, Windsor, ON, Canada, Ontario N9A 3X4 14 Feb 2026

Blaze of Story featuring Paulina O’Kieffe

Café Amor & Art 13 Jan 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

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

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

Folk Festival 2026

5225 Howard Ave, , LaSalle, ON, Canada, Ontario N9H 0J2 7 Feb 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

Chili Fest

201 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 5K4 11 Feb 2026

School House and Braden Lam presents “The Freewheelin’ Field Trip” at Meteor

Meteor 20 Mar 2026

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

The Tipsy Toucan 31 Jan 2026

Pasta Fest

201 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 5K4 12 Mar 2026

Asylum: Windsor's Dark Alternative night

VillainsBeastro Windsor 7 Feb 2026

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

The Tipsy Toucan 7 Mar 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

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

The Tipsy Toucan 4 Apr 2026

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

The Tipsy Toucan 23 May 2026