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

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

St. Patrick's Day in Sandwich Town 6 pubs, live music, great food, Irish dancing, give-aways, & more

 Tue, 17 Mar at 10:00 am Sandwich Street, Windsor, ON, Canada, Ontario

Weird Al Yankovic with Puddles Piddy Party

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

Jann Arden

 Thu, 18 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

Devo

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

Sloan in Windsor

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

Live in Windsor the Hip Experience

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

Jordan Davis at The Colosseum at Caesars Windsor

 Sat, 27 Jun at 08:00 pm 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

VIP CLASSIC HITS Collective Soul SHINES IN WINDSOR!

 Fri, 27 Mar at 08:00 pm Caesars Windsor

George Thorogood & The Destroyers

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

TBD at Windsor Spitfires - OHL Finals (Home Game 4)

 Thu, 21 May at 07:30 am WFCU Centre

George Thorogood and the Destroyers at The Colosseum at Caesars Windsor

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

Collective Soul

 Thu, 26 Mar at 07:00 pm The Colosseum At Caesars Windsor

The Great Catsby Gala

 Sat, 18 Apr at 06:00 pm Giovanni Caboto Club

Snowed in Comedy Tour- Windsor

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

Lord Huron at The Colosseum at Caesars Windsor

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

TBD at Windsor Spitfires - OHL Western Conference First Round (Home Game 4)

 Sun, 05 Apr WFCU Centre

Windsor International Black Film Festival

 Fri, 14 Aug at 05:00 pm 353 Freedom Way, Windsor, ON N9A 0C7, Canada

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

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

Windsor's Biggest Cinco de Mayo Party

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

Cinco de Mayo

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

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

 Sat, 04 Apr at 08:00 pm The Tipsy Toucan CAD 25

Bed By 10 Is Coming To Windsor!

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

Danger Cats Comedy Live in Windsor March 13 🔥

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

Sip & Thrift Vintage Market

 Fri, 08 May at 05:00 pm 400 Erie Street East, Windsor, ON, Canada, Ontario N9A 3X4

Lord Huron

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

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

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

St. Patrick's Day Party at WindsorEats

 Tue, 17 Mar at 02:00 pm WindsorEats

Mary Poppins Jr.

 Fri, 27 Mar Chrysler Theatre

Legends of Motown at Chrysler Theatre

 Fri, 13 Mar at 08:00 pm Chrysler Theatre

Salsa Fever Cruise with Latin Power Band

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

TEJAS D DHOKE - BOLLYWOOD WORKSHOP IN WINDSOR

 Sun, 29 Mar at 04:00 pm Dance Barre CAD 31 to 60

The Wizard of Oz

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

Windsor Symphony Orchestra - Mendelssohn's Elijah at Capitol Theatre

 Sat, 07 Mar at 07:30 pm Capitol Theatre

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

 Sat, 21 Mar at 08:00 pm The Tipsy Toucan CAD 25

80's & 90's Double Wham Jam

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

Jokes On Us Comedy Tour LIVE At Tipsy Toucan

 Fri, 13 Mar at 08:00 pm The Tipsy Toucan CAD 17

Opportunity Bridal - Wedding Dress Sale - Windsor

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

Night of Rock Legends: Led Zeppelin meets Pearl Jam

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

Disney's Mary Poppins Jr. at Chrysler Theatre

 Sat, 28 Mar at 02:00 pm Chrysler Theatre

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

Two Asians One Mic | STAND UP COMEDY TOUR - 2026

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

We're The Problem Comedy Tour LIVE At Tipsy Toucan

 Sat, 18 Apr at 08:00 pm The Tipsy Toucan CAD 25

Cat Clyde in Windsor

 Thu, 28 May at 07:00 pm Meteor

Windsor Symphony Orchestra - Sultans of String at Capitol Theatre

 Sat, 18 Apr at 07:30 pm Capitol Theatre

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

Fri, 20 Mar at 07:30 pm Meteor

Yelawolf VIP Meet & Greet - "The Colosseum at Caesers" - Windsor, ON - 2026/03/26

 Thu, 26 Mar at 05:00 pm Caesars Windsor Colosseum

Le Festival du Nain Rouge

 Sat, 28 Mar at 01:00 pm Windsor, ON, Canada, Ontario N8w3K7

Gilligan's Island 3 Hour Tour

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

Mudmen RC Legion Br 255 Windsor Ontario

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

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

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

Y2K Cruise

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

Family Concert: The Jungle Book

 Sat, 11 Apr at 10:00 am 121 University Avenue, West, Windsor, ON, Canada, Ontario N9A 5P4

The Rule Of Three Comedy Competition

 Sat, 25 Apr at 07:30 pm 138 University Ave W CAD 12

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

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

Tatiana Frank LIVE Comedy At Tipsy Toucan (Apr 24th)

 Fri, 24 Apr at 08:00 pm The Tipsy Toucan CAD 28

HipHop & Heels IWD2026 Event

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

Bande Bano Bande in Windsor (Play By Rana Ranbir)

 Sun, 08 Mar at 04:30 pm Serbian Centre CAD 28 to 39

Superstars - Live Music and Dance Tribute

 Sun, 15 Mar at 04:00 pm 2418 Central Ave, Windsor, ON, Canada, Ontario N8W4J3

ACT Presents: Six: Teen Edition

 Sun, 10 May at 02:00 pm Capitol Theatre Windsor

1999 - The Ultimate Prince Experience

 Thu, 09 Jul at 07:00 pm Chrysler Theatre

Father's Day Cruise-Bridge Tour

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

Mudmen Riverside RC Legion Br 255 Windsor Ontario

 Sat, 11 Apr at 08:00 pm Windsor, Ontario, Canada

The Hangover Comedy Show - At WindsorEats

 Wed, 18 Mar at 08:00 pm WindsorEats Food Hall CAD 21 to 23

Expendable Youth Live on Macassa Bay!

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

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

Devo

 Sat, 06 Jun The Colosseum at Caesars Windsor

Fashion Week Windsor-Essex 2026 Fashion Mixer

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

Tyler Horvath LIVE Comedy At Tipsy Toucan (Apr 2nd)

 Thu, 02 Apr at 08:00 pm The Tipsy Toucan CAD 28

Windsor Symphony Orchestra - Lillian Plays Boccherini at Capitol Theatre

 Thu, 12 Mar at 07:30 pm Capitol Theatre

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

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

DANCING AT LUGHNASA by Korda

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

Solitary Man - A Tribute To Neil Diamond

 Fri, 13 Mar at 07:00 pm Chrysler Theatre

D.B Presents Scale The System Tour with Locksmith & GoonTown & Kahdyn

 Thu, 21 May at 07:00 pm Phog Lounge CAD 33

SQuiRT

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

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

 Sat, 09 May at 08:00 pm The Tipsy Toucan CAD 21

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 at 03:00 pm Chrysler Theatre

Guerrilla Radio - Tribute to Rage Against the Machine

Fri, 20 Mar at 03:00 pm The Cherry Rock Lounge

🎤🎲 THE REMATCH: Karaoke Night at Putali Chowk 🎲🎤

 Sat, 21 Mar at 08:00 pm Putali Chowk Board Games & Bar

Rose City Romance 2026

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

MARCH MADNESS CONCERT

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

WSB Save the Date - March Social

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

Hook & Ladder Presents: Fire House Comedy

 Sat, 11 Apr at 05:30 pm The hook & ladder

Loud Love - Two Legends - One Night

 Thu, 02 Apr at 06:30 pm Polish Club Windsor CAD 23

The Hook & Ladder Presents: Fire House Comedy

 Sat, 11 Apr at 06:00 pm 3690 Seminole St Free

After Dark Walkerville Speakeasy 2026

 Sat, 11 Apr at 07:00 pm Royal Canadian Legion, Ambassador & Walkerville Branch 644 Windsor, Ontario

Bake Club at Windsor Eats | St. Patrick's Day

 Sun, 15 Mar at 03:00 pm 400 Erie St E CAD 17

"ROOSTER" IN-PERSON PAINT PARTY at CRAMDON'S TAP & EATERY

 Wed, 01 Apr at 06:30 pm Cramdon's Tap & Eatery

Chris Cohen (formerly of Deerhoof) w/ Tea Leaves at Meteor

Thu, 26 Mar at 08:00 pm Meteor

The Big Clue Done-it

 Fri, 27 Mar at 07:00 pm Chapter Two Brewing Company CAD 12

Parking Jordan Davis

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

The Pop Yard Bloom Edition

 Sat, 28 Mar at 10:00 am Club 9 Banquet Hall Free

The Goat, or Who Is Sylvia? by Edward Albee

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