Entertainment events in Windsor

Check out happening entertainment events all around Windsor, ON

Jimmy Carr: Laughs Funny

 Tue, 13 Oct at 07:30 pm 8787 McHugh Street, Windsor, ON, Canada, Ontario N8S 0A1

Weird Al Yankovic

 Fri, 03 Jul at 07:00 pm The Colosseum At Caesars Windsor

Daniel Tosh at The Colosseum at Caesars Windsor

 Thu, 25 Jun at 08:00 pm The Colosseum at Caesars Windsor

The Black Keys

 Sat, 17 Oct The Colosseum At Caesars Windsor

Daniel Tosh

 Wed, 24 Jun at 07:00 pm The Colosseum At Caesars Windsor

Bert Kreischer at The Colosseum at Caesars Windsor

 Thu, 01 Oct at 08:00 pm The Colosseum at Caesars Windsor

Bert Kreischer

 Wed, 30 Sep at 07:00 pm The Colosseum At Caesars Windsor

UB40

 Sat, 03 Oct at 12:00 am The Colosseum at Caesars Windsor

Jann Arden at The Colosseum at Caesars Windsor

 Fri, 19 Jun at 08:00 pm The Colosseum at Caesars Windsor

Jordan Davis at The Colosseum at Caesars Windsor

 Sat, 27 Jun at 08:00 pm The Colosseum at Caesars Windsor

Nelly at The Colosseum at Caesars Windsor

 Thu, 16 Jul at 08:00 pm The Colosseum at Caesars Windsor

The Black Keys Tickets

 Sun, 18 Oct at 07:30 pm Windsor, Ontario, Canada

Weird Al Yankovic with Puddles Piddy Party

 Sun, 05 Jul at 12:00 am The Colosseum at Caesars Windsor

Seth Meyers

 Fri, 10 Jul at 07:00 pm The Colosseum At Caesars Windsor

Jann Arden

 Thu, 18 Jun at 07:00 pm The Colosseum At Caesars Windsor

Devo Tickets

Fri, 05 Jun at 08:00 pm Caesars Windsor Colosseum

Devo

 Thu, 04 Jun at 07:00 pm The Colosseum At Caesars Windsor

Family Father's Day Charity Extravaganza

Sat, 20 Jun at 10:00 am SportsPlex Fitness St. Clair College

Windsor Carnival 2026

 Thu, 20 Aug at 10:00 am Lanspeary Outdoor Rink

The Australian Pink Floyd Show

 Fri, 28 Aug at 12:00 am The Colosseum at Caesars Windsor

Bush & JJ Wilde

 Wed, 22 Jul at 07:00 pm The Colosseum At Caesars Windsor

Seth Meyers

 Sun, 12 Jul at 12:00 am The Colosseum at Caesars Windsor

2026 Electric Avenue International Jazz Festival

 Fri, 03 Jul at 06:00 pm WindsorEats

Rock the Walk Fashion & Live Music Celebration

 Sat, 13 Jun at 05:30 pm St. Clair College Centre for the Arts

Retro Silent Disco | Water's Edge Event Centre | Windsor

 Sat, 18 Jul at 05:30 pm Water's Edge Event Centre CAD 45 to 70

The Australian Pink Floyd Show: The Happiest Days Of Our Lives

 Thu, 27 Aug at 08:00 pm The Colosseum at Caesars Windsor

Windsor Riverfront Fireworks Party at the Bistro

 Mon, 22 Jun at 06:00 pm The Riverfront Bistro CAD 134 to 933

Lord Huron

 Mon, 13 Jul at 12:00 am The Colosseum at Caesars Windsor

Windsor International Black Film Festival

 Thu, 13 Aug at 09:00 am 353 Freedom Way, Windsor, ON N9A 0C7, Canada

Mystic Garden Music Festival 2026

 Sat, 11 Jul at 12:00 pm 1250 Langlois Ave, Windsor, ON, Canada

Warren Zeiders

 Thu, 06 Aug The Colosseum At Caesars Windsor

A Night In Nashville

Sat, 23 May at 06:00 pm Pélissier Street Parking Garage

MAPLE LEAF PRO Wrestling MAYHEM on TSN TV Tapings

 Fri, 12 Jun at 07:00 pm St. Clair College CAD 32 to 213

NCG WRESTLING PRESENTS " THE NIGHT BEFORE THE BIG EVENT"

 Fri, 19 Jun at 07:00 pm Portofino Riverside Tower Inc CAD 301

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

 Sat, 30 May at 08:00 pm The Tipsy Toucan CAD 25

SYNC

 Fri, 17 Jul at 04:00 pm Festival Plaza Park CAD 116 to 278

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

 Sat, 19 Sep at 08:00 pm The Tipsy Toucan CAD 28

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

 Sat, 27 Jun at 08:00 pm The Tipsy Toucan CAD 25

Windsor Ladies Night

 Sat, 27 Jun at 02:30 pm 1190 Wyandotte St W CAD 39

Foreign Journey in Windsor

 Sat, 19 Sep at 07:30 pm The Chrysler Theatre

80's & 90's Double Wham Jam

 Sat, 25 Jul at 08:00 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4

Windsor Sunset Party Cruise with Jean-Luc and Nick

 Sat, 18 Jul at 06:45 pm 78 Riverside Dr W, Windsor, ON N9A 0A3, Canada

Taste of Walkerville

 Sat, 12 Sep at 11:00 am Wyandotte St E, Windsor, ON, Canada

WIFF Under the Stars - FREE Outdoor Movies

 Fri, 12 Jun at 09:00 am 421 Riverside Dr W, Windsor, ON N9A 7J1, Canada

Billy Raffoul in Windsor

 Sat, 13 Jun at 07:00 pm St. Clair College Centre for the Arts

Salsa Fever Cruise with Latin Power Band

 Sat, 01 Aug at 08:00 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4

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

 Sat, 25 Jul at 08:00 pm The Tipsy Toucan CAD 25

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

 Sat, 11 Jul at 08:00 pm The Tipsy Toucan CAD 25

Devo

 Sat, 06 Jun at 12:00 am The Colosseum at Caesars Windsor

1999 - The Ultimate Prince Experience

 Thu, 09 Jul at 07:00 pm Chrysler Theatre

Lord Huron at The Colosseum at Caesars Windsor

 Sun, 12 Jul The Colosseum at Caesars Windsor

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

 Sat, 20 Jun at 08:00 pm The Tipsy Toucan CAD 25

Josh Ross: Later Tonight Tour

 Sat, 14 Nov at 08:00 pm The Colosseum at Caesars Windsor

Cat Clyde in Windsor

 Thu, 28 May at 07:00 pm Meteor

We Three Kings: The Multinational Tribute to Elvis ~ WINDSOR

 Wed, 03 Jun at 07:30 pm RockStar Music Hall

89NEXT Rocks with Windsor Premier Cruises!

 Sat, 15 Aug at 08:00 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4

SQuiRT

 Fri, 22 May at 09:00 pm Prototype CAD 35 to 39

Warren Zeiders

 Fri, 07 Aug at 08:00 pm The Colosseum at Caesars Windsor

PorkChops Comedy - Windsor, On

 Fri, 12 Jun at 07:00 pm The Cherry Rock Lounge CAD 33

Jeff Leeson at Chrysler Theatre

 Fri, 23 Oct at 08:00 pm Chrysler Theatre

SECRET HOURS: Windsor’s Hottest Dancehall x Afrobeat x Hip-Hop Party

 Sat, 13 Jun at 10:00 pm Diva's Delite Caribbean and Canadian Cuisine CAD 23

Canadas Circus Spectacular at WFCU Centre

 Sun, 14 Jun WFCU Centre

SNL Pub Crawl

 Sun, 28 Jun at 01:00 pm 400 Erie Street East, Windsor, ON, Canada, Ontario N9A 3X4

Strings: A Marionette's Tale

 Fri, 19 Jun at 07:00 pm Capitol Theatre CAD 23 to 28

Julie Doiron / Carson McHone at Meteor

Mon, 22 Jun at 08:00 pm Meteor

Y2K Cruise

 Sat, 11 Jul at 08:00 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4

Erie St GastroPub - Block Party

 Sat, 23 May at 10:00 am Erie St GastroPub Free

Father's Day Cruise-Bridge Tour

 Sun, 21 Jun at 02:00 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4

Expendable Youth Live on Macassa Bay!

 Sat, 13 Jun at 07:00 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4

Gilligan's Island 3 Hour Tour

 Fri, 24 Jul at 07:00 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4

MagicBox: An Evening of Wonder

 Sat, 23 May at 08:00 pm The Shadowbox Theatre CAD 28

Square Dance Night

 Sat, 23 May at 07:00 pm Walkerville Brewery CAD 12

Funny to be HERE: An afternoon comedy showcase at WindsorEats

 Sat, 30 May at 03:30 pm WindsorEats Food Hall CAD 18

Alistair Ogden's Here For You | Live Stand Up Comedy in Windsor

 Sat, 08 Aug at 08:00 pm Windsor Laughs Comedy Club at The Tipsy Toucan CAD 21 to 28

Windsor-Essex Christmas Market 2026 - Part 1

 Sat, 14 Nov at 12:00 pm THE WFCU CENTRE

Pinoyz II Men(Norm Alconcel/Ernie Vincente) LIVE At Tipsy Toucan (June 6th)

 Sat, 06 Jun at 08:00 pm The Tipsy Toucan CAD 25

The Rule Of Three

 Sat, 22 Aug at 08:00 pm 138 University Ave W CAD 12

His Sinatra

 Fri, 07 Aug at 07:00 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4

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

 Sat, 29 Aug at 08:00 pm The Tipsy Toucan CAD 25

Henry Sir: Live In Windsor

 Thu, 24 Sep at 07:00 pm Windsor Laughs Comedy Club at The Tipsy Toucan CAD 26 to 32

RIDE THE CYCLONE by Korda

 Fri, 12 Jun at 08:00 pm 2520 Seminole St, Windsor, ON, Canada, Ontario N8Y 1X4

WinKizX 2026 – Windsor Kizomba Exchange (2nd Edition)

 Fri, 18 Sep at 06:00 pm Hellenic Cultural Centre Windsor

Windsor Pop Up Wedding Dress Sale

 Sun, 28 Jun at 09:00 am Giovanni Caboto Club 2175 Parent Ave, Windsor, ON

Diablerie Vampire Ball

 Sat, 17 Oct at 08:00 pm Water's Edge Event Centre CAD 65 to 150

Sonata Music Adventures Live In Concert!

 Sat, 30 May at 02:00 pm Capitol Theatre Windsor CAD 0 to 55

Parking Jordan Davis

 Sun, 28 Jun at 12:00 am The Colosseum at Caesars Windsor

The Piano Men

 Sat, 14 Nov at 06:00 pm 201 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 5K4

BOLLYWOOD DANCE WORKSHOP

 Sat, 23 May at 02:00 pm Cathy's Dance Studio Inc CAD 15 to 30

Opportunity Bridal - Wedding Dress Sale - Windsor

 Sat, 14 Mar Giovanni Caboto Club CAD 0 to 54

A Night of Ghazals with Rhea Zaki

 Sat, 11 Jul at 06:00 pm Giovanni Caboto Club CAD 23 to 44

TRILOGY CLASSICS LIVE presents FOREIGN JOURNEY at the CHRYSLER CENTRE, WINDSOR, ON

 Sat, 19 Sep at 07:30 pm The Chrysler Theatre

Foxwarren at Meteor

Tue, 07 Jul at 07:00 pm Meteor

The Deadly Romantics - It's Gettin' Harder 2026 - Windsor

 Sat, 30 May at 08:00 pm The Cherry Rock Lounge

The Newcomers Stand-up Comedy Show

 Fri, 05 Jun at 07:00 pm The Shadowbox Theatre CAD 23

True North Voices

 Fri, 03 Jul at 08:00 pm Capitol Theatre Windsor CAD 28

BollyXKuthu Dance Workshop & Fun Social Windsor

 Sat, 30 May at 03:00 pm Mackenzie Hall Cultural Centre CAD 18 to 23

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

 Fri, 27 Feb at 08:00 pm Lion's Head Tavern USD 28

3rd Annual R.Y.O.T. For Charity Pre-Halloween Bash🎃

Sat, 17 Oct at 07:00 pm Meteor

Cat Clyde

 Wed, 27 May at 07:00 pm Meteor - Windsor

WSB Save the Date - June 26th 2026

 Fri, 26 Jun at 08:00 pm Polish Club Windsor