Windsor Festivals Events

Dave Merheje-Summer Edition LIVE Comedy At Tipsy Toucan (July 31st)

The Tipsy Toucan 31 Jul 2026

Windsor 2nd Annual Asian Night Market

Festival Plaza 27 Aug 2026

Windsor Carnival 2026

Lanspeary Outdoor Rink 20 Aug 2026

LiUNA!625 Family Father's Day Extravaganza

SportsPlex Fitness St. Clair College 20 Jun 2026

2026 Electric Avenue International Jazz Festival

WindsorEats 3 Jul 2026

Mexican Village for Carrousel of the Nations

400 Erie Street East, Windsor, ON, Canada, Ontario N9A 3X4 12 Jun 2026

2026 Chinese Village at Carousel of Nations

1420 Tecumseh Road East, Windsor, ON, Canada 13 Jun 2026

Windsor International Black Film Festival

353 Freedom Way, Windsor, ON N9A 0C7, Canada 13 Aug 2026

Keesha Brownie LIVE Comedy At Tipsy Toucan (June 27th)

The Tipsy Toucan 27 Jun 2026

2026 Windsor Waterfront Half Marathon + 5K

Riverfront Festival Plaza 13 Sep 2026

Kyle Lucey LIVE Comedy At Tipsy Toucan (July 4th)

The Tipsy Toucan 4 Jul 2026

Mystic Garden Music Festival 2026

1250 Langlois Ave, Windsor, ON, Canada 11 Jul 2026

Ron Josol LIVE Comedy At Tipsy Toucan (Nov 7th)

The Tipsy Toucan 7 Nov 2026

SYNC

Festival Plaza Park 17 Jul 2026

Danny Martinello LIVE Comedy At Tipsy Toucan (Sep 19th)

The Tipsy Toucan 19 Sep 2026

CHARIOT FESTIVAL (Ratha-Yatra 2026)

Lanspeary Park 1 Aug 2026

Ghost Ship

78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4 17 Oct 2026

Taste of Walkerville

Wyandotte St E, Windsor, ON, Canada 12 Sep 2026

Jeremy Dobski LIVE Comedy At Tipsy Toucan (July 25th)

The Tipsy Toucan 25 Jul 2026

The Bridge: DETROIT Edition LIVE Comedy At Tipsy Toucan (July 11th)

The Tipsy Toucan 11 Jul 2026

Jason Allen LIVE Comedy At Tipsy Toucan (June 20th)

The Tipsy Toucan 20 Jun 2026

Armin Arbabi LIVE Comedy At Tipsy Toucan (Aug 22nd)

The Tipsy Toucan 22 Aug 2026

Hassan Phills: Live in Windsor

Windsor Laughs Comedy Club at The Tipsy Toucan 20 Nov 2026

2-Minutes To K*ll Summer Edition - Comedians Compete for $1,000 & A Cruise!

Pelissier Parking Garage 27 Jun 2026

Carousel of the Nations : GHANA

1093 drouillard road, Windsor, ON, Canada, Ontario N8y 2p9 13 Jun 2026

TULUM VIBES!

ekō 2 Aug 2026

Desi AF Featuring: Sonya Vai

Meteor 20 Jun 2026

Nick Burden LIVE Comedy At Tipsy Toucan (Aug 29th)

The Tipsy Toucan 29 Aug 2026

Erie St GastroPub - Block Party

Erie St GastroPub 23 May 2026

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

The Tipsy Toucan 14 Nov 2026

WINDSOR HIP HOP FESTIVAL 2026

Atkinson Park 8 Aug 2026

Northern Heat Ribfest Devonshire Mall !!! Crooked Swagger Live

Devonshire Mall 28 Aug 2026

Windsor' NEW Ribfest presents Wicked Truth

Devonshire Mall 29 Aug 2026

Windsor Jerk Fest 2026

2410 Central Ave 26 Jun 2026

Lost Charm / Sunforger / No Saviors at Meteor

Meteor 10 Jul 2026

Alexa Stanton LIVE Comedy At Tipsy Toucan (Aug 15th)

The Tipsy Toucan 15 Aug 2026

Carrousel of Nations African Village

1356 Tecumseh Rd. W., Windsor, ON, Canada 19 Jun 2026

Black Film Festival

353 Freedom Way, Windsor, ON N9A 0C7, Canada 13 Aug 2026

Dream Nails (UK) / Bird Witness / Seedy CD’s at Meteor

Meteor 2 Jul 2026

Serenity Summerfest

2335 Dougall Ave., Windsor, ON, Canada, Ontario N8X1S9 13 Jun 2026

Drumming Down the Sun

Peace Fountain 4 Jun 2026