Entertainment events in Windsor

Check out happening entertainment events all around Windsor, ON

Weird Al Yankovic

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

Paul Anka

 Sun, 12 Apr at 12:00 am 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

Daniel Tosh

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

Dylan Scott at The Colosseum at Caesars Windsor

 Sat, 25 Apr at 08:00 pm The Colosseum at Caesars Windsor

MAPLE LEAF PRO WRESTLING Presents ROH x MLP Global Wars & MLP Uprising

 Fri, 27 Mar at 07:00 pm St. Clair College CAD 32 to 213

Steve O - Stephen Gilchrist Glover at Chrysler Theatre

 Thu, 12 Feb at 08:00 pm Chrysler Theatre

Steve-O

 Wed, 11 Feb at 07:00 pm Chrysler Theatre

Jordan Davis at The Colosseum at Caesars Windsor

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

George Thorogood and the Destroyers at The Colosseum at Caesars Windsor

 Thu, 21 May at 07:30 pm The Colosseum at Caesars Windsor

George Thorogood & The Destroyers

 Thu, 21 May at 11:30 pm The Colosseum at Caesars Windsor

Mardi Gras Extravaganza 2026!

 Fri, 27 Feb at 06:00 pm Fogolar Furlan Club of Windsor

Lord Huron at The Colosseum at Caesars Windsor

 Sun, 12 Jul at 08:00 pm The Colosseum at Caesars Windsor

Daniel Tosh: My First Farewell Tour

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

Sloan in Windsor

 Sat, 14 Mar at 07:00 pm Capitol Theatre Windsor

Love Hurts Valentine's Popup

 Fri, 13 Feb at 05:00 pm WindsorEats

Snowed in Comedy Tour- Windsor

 Tue, 07 Apr at 03:00 pm Capitol Theatre Windsor

HANNAH BERNER: NONE OF MY BUSINESS TOUR

 Thu, 19 Feb at 08:00 pm The Colosseum at Caesars Windsor

Bed By 10 Is Coming To Windsor!

 Sat, 18 Apr at 04:00 pm Disco Inferno Windsor

Parking Flint Firebirds at Windsor Spitfires

 Sat, 24 Jan at 12:05 am WFCU Centre

Hannah Berner

 Wed, 18 Feb at 07:00 pm The Colosseum At Caesars Windsor

Lord Huron

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

Cinco de Mayo

 Sun, 03 May at 12:00 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4

The Fab Four: The Ultimate Tribute

 Thu, 12 Feb at 08:00 pm The Colosseum at Caesars Windsor

89NEXT - Valentine's Day Show

 Sat, 14 Feb at 09:00 pm The Cherry Rock Lounge

Windsor Symphony Orchestra - Mendelssohn's Elijah at Capitol Theatre

 Sat, 07 Mar at 07:30 pm Capitol Theatre

Sarnia Sting at Windsor Spitfires at WFCU Centre

 Sun, 01 Feb at 07:00 pm WFCU Centre

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

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

The Trews with Special Guest Crown Lands

 Sat, 28 Feb at 08:00 pm The Colosseum at Caesars Windsor

Lee Siegel Sings Broadway

 Sat, 14 Feb at 07:30 pm 121 University Avenue, West, Windsor, ON, Canada, Ontario N9A 5P4

Red Astro - A Tribute to The Red Hot Chili Pepppers

 Sat, 28 Feb at 09:00 pm The Cherry Rock Lounge

Laughs & Love: A Valentine’s Comedy Show - Windsor

 Sat, 14 Feb at 07:00 pm The Cherry Rock Lounge CAD 28

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

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

BAD EXAMPLES 12TH ANNUAL CONCERT FUNDRAISER ZZ TOP TRIBUTE

 Sat, 28 Feb at 07:00 pm Serbian Centre CAD 44

Black Orchids' Valentine's Day Celebration

 Sat, 14 Feb at 05:00 pm Royal Canadian Legion, Ambassador & Walkerville Branch 644 Windsor, Ontario

Legends of Motown at Chrysler Theatre

 Fri, 13 Mar Chrysler Theatre

Windsor Express

 Mon, 23 Feb The Colosseum At Caesars Windsor

Forever Seger - A Tribute to the Music of Bob Seger

 Sat, 07 Mar at 08:00 pm The Chrysler Theatre

Y2K Cruise

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

Night of Rock Legends: Led Zeppelin meets Pearl Jam

 Sat, 21 Mar at 08:00 pm The Chrysler Theatre

The Broadway Bunch: All Ages

 Fri, 27 Feb at 08:00 pm Meteor

Dirty Bingo

 Fri, 13 Feb at 07:00 pm TQLA CAD 10

Windsor Symphony Orchestra - Sultans of String at Capitol Theatre

 Sat, 18 Apr at 07:30 pm Capitol Theatre

Bake Club | Club Love at Windsor Eats

 Sun, 08 Feb at 03:00 pm 400 Erie St E CAD 17

The Wizard of Oz

 Thu, 26 Mar at 07:30 pm Templeblooms at the Masonic Ballroom

Dueling Pianos

 Thu, 19 Feb at 07:00 pm Walkerville Brewery CAD 17

Windsor Symphony Orchestra - Lillian Plays Boccherini at Capitol Theatre

 Thu, 12 Mar at 07:30 pm Capitol Theatre

Danger Cats Comedy Live in Windsor March 13 🔥

 Fri, 13 Mar at 07:00 pm The Cherry Rock Lounge

Father's Day Cruise-Bridge Tour

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

Valentine's Jazz Night at Walkerville Brewery

 Sat, 14 Feb at 08:00 pm Walkerville Brewery CAD 12

It’s 5 O’Clock Somewhere Fest

 Sun, 22 Feb at 01:00 pm Phog Lounge CAD 28

Live in Windsor the Hip Experience

Fri, 17 Apr at 09:00 pm The Cherry Rock Lounge

Date on Purpose: The Intentional Dating Experience (Ages 50–65+)

 Wed, 18 Feb at 06:30 pm Wineology CAD 68

TRIPLE X OH!

 Sat, 21 Feb at 07:00 pm Chapter Two Brewing Company CAD 12

Laugh-A-Rita Comedy Night at Treehouse!

 Sun, 22 Feb at 05:00 pm Treehouse CAD 6 to 17

HipHop & Heels IWD2026 Event

 Sat, 07 Mar at 07:00 pm The Well Windsor CAD 15 to 75

FACS w/ Bog Moss at Meteor

Sun, 15 Feb at 08:00 pm Meteor

From The Hip a celebration of The Tragically Hip wsg This Thing We Started

 Sat, 28 Mar at 07:00 pm Serbian Centre CAD 33

Fashion Week Windsor-Essex 2026 Fashion Mixer

 Thu, 26 Mar at 06:00 pm Art Windsor-Essex CAD 39

Curious George and the Golden Meatball

 Wed, 18 Mar at 07:00 pm Chrysler Theatre

Curious George and The Golden Meatball at Chrysler Theatre

 Thu, 19 Mar Chrysler Theatre

SQuiRT

 Fri, 22 May at 09:00 pm 44 University Ave W CAD 44

DANCING AT LUGHNASA by Korda

 Fri, 13 Mar at 08:00 pm 2520 Seminole St, Windsor, ON, Canada, Ontario N8Y 1X4

Release Your Negativity -Didgeridoo Sound / Color Vibrational Attunement, Meditation & Sound Bath

Sat, 21 Feb at 07:00 pm The Shala Yoga & Meditation Studio

Dinner and a Movie- PRETTY WOMAN

 Sat, 14 Feb at 06:00 pm 201 Riverside Dr W, Windsor, ON, Canada

Day of the Dude

 Fri, 06 Mar at 05:00 pm WindsorEats

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

 Sat, 28 Mar at 08:00 pm The Tipsy Toucan CAD 25

IMPROV is the OPPOSITE OF AI - Be Original in the Improv for Beginners Class

 Wed, 11 Feb at 06:00 pm Kordazone Theatre

Rose City Romance 2026

 Fri, 10 Apr at 09:00 am Caesars Windsor CAD 4 to 310

COLDHEARTED! - a Kat Valentine special

 Wed, 11 Feb at 10:00 pm The Cherry Rock Lounge CAD 7

ekō.one [Roice + Ex Libris]

 Sun, 15 Feb at 08:00 pm ekō Free

St. Patrick's Day Party at WindsorEats

 Tue, 17 Mar at 02:00 pm WindsorEats

Dreamboats at Chrysler Theatre

 Fri, 13 Feb Chrysler Theatre

Parking Peterborough Petes at Windsor Spitfires

 Fri, 27 Feb at 12:05 am WFCU Centre

LEASH - A Tribute to Pearl Jam

 Sat, 07 Mar at 09:00 pm The Cherry Rock Lounge

Pop Punk’s Not Dead w/ Drink-182 and Expendable Youth

 Sat, 11 Apr at 10:00 pm The Cherry Rock Lounge CAD 12

MARCH MADNESS CONCERT

 Sat, 21 Mar at 09:00 pm Joywave CAD 12

MCC Create Your Career Day

 Thu, 19 Feb at 09:30 am Capitol Theatre Windsor Free

WSB Save the Date - February Social

 Fri, 27 Feb at 08:00 pm Hellenic Cultural Centre

Galentine's Day Magical Tea Party

 Fri, 13 Feb at 06:00 pm 1295 Ottawa Street, Windsor, ON, Canada

I LOVE DRUM N' BASS!

 Fri, 13 Feb at 06:30 pm ekō CAD 44

BAD EXAMPLES 12TH ANNUAL CONCERT FUNDRAISER.

 Sat, 28 Feb at 07:00 pm Windsor, ON, Canada, Ontario N9A3L2

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

Fri, 20 Mar at 07:30 pm Meteor

Soul City Music Co-op Winter Showcase

 Fri, 20 Feb at 08:30 pm Meteor CAD 27

Parking Jordan Davis

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

James Franchise Band

 Sun, 29 Mar at 08:00 pm 2300 Huron Church Rd CAD 28 to 39

Paczki Party

 Tue, 17 Feb at 05:00 pm WindsorEats

WSB Save the Date - March Social

 Fri, 27 Mar at 08:00 pm Hellenic Cultural Centre

Windsor's Biggest Cinco de Mayo Party

 Fri, 01 May at 05:00 pm 400 Erie Street East, Windsor, ON, Canada, Ontario N9A 3X4

Two Asians One Mic | STAND UP COMEDY TOUR - 2026

 Sat, 28 Mar at 08:00 pm Meteor CAD 38

Beyond The Spotlight

 Sat, 28 Feb at 07:00 pm Chrysler Theatre

Sonata on Stage Presents: Shrek Jr. The Musical (Sunday 6PM)

 Sun, 26 Apr at 06:00 pm École secondaire catholique l'Essor CAD 0 to 22

Pony at Meteor

Thu, 19 Feb at 08:00 pm Meteor

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

 Sat, 14 Mar at 08:00 pm The Tipsy Toucan CAD 21

Beyond The Spotlight at Chrysler Theatre

 Sun, 01 Mar Chrysler Theatre

Sonata Music Adventures Live In Concert!

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

Mudmen RC Legion Br 255 Windsor Ontario

 Sat, 11 Apr at 08:00 pm Royal Canadian Legion Branch 255

The Goat, or Who Is Sylvia? by Edward Albee

 Fri, 13 Mar at 08:00 pm The Shadowbox Theatre

Opportunity Bridal - Wedding Dress Sale - Windsor

 Sat, 14 Mar at 09:00 am Giovanni Caboto Club CAD 0 to 54

Windsor Pop Up Wedding Dress Sale

 Sat, 14 Mar at 09:00 am Giovanni Caboto Club 2175 Parent Ave, Windsor, ON