Entertainment events in Windsor

Check out happening entertainment events all around Windsor, ON

New Year’s Eve Celebration

Wed, 31 Dec at 06:30 pm 201 Riverside Dr W, Windsor, ON, Canada

Kenny Vs Spenny Live In Windsor

 Fri, 12 Dec at 08:00 pm RockStar Music Hall CAD 48 to 99

Flamekeeper: A Christmas Tale

 Fri, 12 Dec at 07:00 pm Capitol Theatre Windsor

WFCU Holiday Market

 Sat, 13 Dec at 10:00 am THE WFCU CENTRE

Windsor Comedy Club Proshow

 Fri, 12 Dec at 08:00 pm 468 Erie St E CAD 23

Need a Little Christmas

 Sat, 20 Dec at 06:00 pm 986 Ouellette Avenue, Windsor, ON, Canada, Ontario N9A 1C6

Bed By 10 Is Coming To Windsor!

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

An East Coast Christmas

 Fri, 12 Dec at 05:00 pm 400 Erie Street East, Windsor, ON, Canada, Ontario N9A 3X4

The Mrs. Kennedys + The Waybacks – Live at Meteor

 Fri, 19 Dec at 07:00 pm Meteor CAD 8

The Jimmy Show-Christmas Comedy Charity LIVE At The Tipsy Toucan (Dec 20th)

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

The Feedbacks, Black-Eyed Susan, EVL, Bird Witness at Meteor Jan. 3rd

 Sat, 03 Jan at 08:00 pm Meteor

Tim Reaburn's Heckle Show at Windsor Comedy Club vol.1

 Tue, 30 Dec at 08:30 pm 89 university ave west, Windsor, ON, Canada, Ontario

A Very Wild Christmas

 Sat, 20 Dec at 10:00 pm 527 Ouellette Ave, Windsor, ON, Canada, Ontario N9A 4J3

ANNIE OF GREEN GABLES, GET YOUR GUN by Korda

 Thu, 11 Dec at 07:00 pm 2520 Seminole St, Windsor, ON, Canada, Ontario N8Y 1X4

Crave by Sarah Kane

 Thu, 11 Dec at 08:00 pm The Shadowbox Theatre

Canada's Drag Race Episode 5 Viewing Party

 Thu, 18 Dec at 07:00 pm The Man's Shop & Barbershop Bar CAD 12 to 28

Beauty and the Beat

 Sat, 24 Jan at 07:30 pm 121 University Avenue, West, Windsor, ON, Canada, Ontario N9A 5P4

MISTER CHRISTMAS | HOLIDAY PARTY by Mister Style

 Fri, 12 Dec at 07:00 pm 1055 Ottawa Street, Windsor, ON, Canada, Ontario N8X 2E3

Christmas Lessons and Carols at Emmanuel United Church

 Sun, 14 Dec at 07:00 pm 1728 Lincoln Road, Windsor, ON, Canada

12 RODS (solo) w/ Meandergreen at Meteor

Sun, 11 Jan at 08:00 pm Meteor

PRO WRESTLING THE BAND + TROPHY KNIFE @ The Dominion House - Nov 13

 Sat, 13 Dec at 09:00 pm Dominion House CAD 12

DESTROYER Canada Tribute to KISS @The Cherry Rock Lounge, Windsor Ontario

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

KENEKTMAS

 Sat, 20 Dec at 09:00 pm 552 Ouellette Ave, Windsor, ON N9A 1B7, Canada

Factory House - Sports & Pop-Culture Trivia Night

 Thu, 18 Dec at 07:00 pm Factory House

A Riverfront Double Feature!

 Fri, 30 Jan at 07:00 pm Paulin Memorial Presbyterian Church

Crooked Swagger Christmas Party !! Boxing day Bash !!!

 Fri, 26 Dec at 09:00 pm Ceasars Windsor Casino

Tinseltown Windsor Christmas Popup Bar

 Thu, 11 Dec at 05:00 pm 400 Erie Street East, Windsor, ON, Canada, Ontario N9A 3X4

Street Survivors

 Sat, 13 Dec at 09:00 pm The Cherry Rock Lounge CAD 9

WSB CHRISTMAS EveEveEveEveEveEve! Ft Denise of AoD!!

 Fri, 19 Dec at 08:00 pm Hellenic Cultural Centre

Round 8: Funniest comedian in Windsor Competition - a part of The Brewing For Comedy Festival III

 Wed, 31 Dec at 08:00 pm 89 university ave west, Windsor, ON, Canada, Ontario

Hot A Heck Comedy Tour - Windsor

 Fri, 19 Dec at 08:00 pm Meteor

❄️ Date on Purpose: Holiday Meet Cute Edition ❄️

 Thu, 11 Dec at 07:00 pm Cookie Bar

Sloan “A Tour de Force” at Capitol Theatre Windsor

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

Canadian Famous Comedy Tour LIVE at The Tipsy Toucan (December 13)

 Sat, 13 Dec at 08:00 pm The Tipsy Toucan CAD 28

AFRICAN VILLAGE END-OF-YEAR PARTY!

 Wed, 24 Dec at 09:00 pm 189 Tecunseh RD W, Windsor, ON, Canada, Ontario N8X 1E8

Definite Leppard - Live at The Cherry

 Sat, 27 Dec at 09:00 pm The Cherry Rock Lounge CAD 14

Uncle Lazer

 Sun, 18 Jan at 09:30 pm Windsor Laughs

A Very Merry Mixer Holiday Workshop

 Fri, 12 Dec at 06:00 pm Cake Cosmetix

The Dirty Show at Windsor Comedy Club

 Tue, 30 Dec at 08:00 pm 89 university ave west, Windsor, ON, Canada, Ontario

New Years Eve Extravaganza At Disco Inferno

 Wed, 31 Dec at 10:00 pm Disco Inferno 29 Park St W, Windsor, ON, Canada, Ontario N9A 4J2

Forever Seger - A Tribute to the Music of Bob Seger

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

Dinner and a Movie- PRETTY WOMAN

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

Jazz Night at the Brewery

 Sun, 28 Dec at 06:00 pm Walkerville Brewery

Andrew Santino at The Colosseum at Caesars Windsor

 Fri, 16 Jan at 08:00 pm The Colosseum at Caesars Windsor

Dave Merheje-Christmas Edition LIVE Comedy At Tipsy Toucan (December 27th)

 Sat, 27 Dec at 08:00 pm The Tipsy Toucan CAD 28

Danger Cats Comedy Live in Windsor March 13 🔥

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

Blanche Presents NYE 2026

 Wed, 31 Dec at 10:00 pm Blanche Restaurant & Lounge CAD 23

Salt of the Chief Cornerstone (album release party) with Huron Lines

 Fri, 12 Dec at 09:00 pm Meteor Bar CAD 10

New Year's Eve with Saints Down

 Wed, 31 Dec at 09:00 pm Windsor Masonic Temple

Culturally Inappropriate | STAND UP COMEDY TOUR | 2025

 Sat, 24 Jan at 08:00 pm Meteor CAD 32

SQUAD UP: Customer Appreciation Party

 Fri, 12 Dec at 10:00 pm 527 Ouellette Ave, Windsor, ON, Canada, Ontario N9A 4J3

NEW YEARS EVE 2025

 Wed, 31 Dec at 07:00 pm 507 Ouellette Avenue, Windsor, ON, Canada, Ontario N9A 4J3

Little Women Movie Night

 Fri, 19 Dec at 06:00 pm Erie Hall CAD 9

Villains Beastro Charity Spotlight Shows

 Fri, 19 Dec at 09:00 pm 256 Pelissier St, Windsor, ON N9A 4K2, Canada

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

 Wed, 10 Dec at 06:30 pm Cramdon's Tap & Eatery

Beauty and the Beat

 Sun, 25 Jan at 02:30 pm 121 University Avenue, West, Windsor, ON, Canada, Ontario N9A 5P4

Purple Parade (Part IV)

 Sat, 13 Dec at 09:00 pm Meteor

Steve-O Crash & Burn Tour Windsor ON

 Thu, 12 Feb at 07:00 pm The Chrysler Theatre

AoD Weekly Dance Practicas

Wed, 10 Dec at 07:00 pm 628 Monmouth Rd. , Windsor, ON, Canada, Ontario N8Y 3L1

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

The PURE Academy Annual Holiday Showcase (Lakeshore Monday/Friday/Saturday Classes Show)

 Wed, 17 Dec at 06:00 pm The Chrysler Theatre

Ho Ho Holiday Bake Club at Windsor Eats Food Hall

 Sun, 14 Dec at 01:00 pm 400 Erie St E CAD 17

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

 Sat, 31 Jan at 07:00 pm Capitol Theatre Windsor CAD 23

SUGAR RUSH

 Fri, 16 Jan at 06:30 pm ekō CAD 55

Taylor Swift Vs Tate McRae Dance Party

 Thu, 18 Dec at 08:00 pm Disco Inferno 29 Park St W, Windsor, ON, Canada, Ontario N9A 4J2

The Tea Party, Headstones & Finger Eleven

 Wed, 10 Dec The Colosseum at Caesars Windsor

Clean Comedian Jim McCue "The Circuit" 53

 Thu, 15 Jan at 07:00 pm 1570 Marentette Ave, Windsor, ON N8X 4E3, Canada

IS it A Wonderful Life?

 Wed, 10 Dec at 06:30 pm 3200 Woodland Drive, Windsor, ON, Canada, Ontario N9E 1Z5

Fledermaus! A Champagne Masquerade

 Thu, 08 Jan at 07:30 pm Capitol Theatre Windsor

Blue Rodeo Tickets Windsor Ontario Canada The Colosseum At Caesars Windsor

 Thu, 08 Jan at 08:00 pm 377 Riverside Dr E, Windsor, ON N9A 7H7, Canada

The PURE Academy Annual Holiday Showcase (Lasalle Show)

 Tue, 16 Dec at 06:00 pm The Chrysler Theatre

Day Zero 2026

 Wed, 31 Dec at 09:00 pm Scarehouse Windsor CAD 32 to 62

Dreamgirls: A Tribute to Donna Summer Dinner Show

 Sat, 24 Jan at 06:00 pm 201 Riverside Dr W, Windsor, ON, Canada

Santa's Cocoa & Candy Cane Social

 Sun, 21 Dec at 03:00 pm 400 Erie Street East, Windsor, ON, Canada, Ontario N9A 3X4

New Years Eve Extravaganza

 Wed, 31 Dec at 05:00 pm 2418 Central Ave, Windsor, ON, Canada, Ontario N8W4J3

Rosstad Yule 2025

 Sat, 20 Dec at 05:00 pm 1441 McDougall St, Windsor, ON N8X 3M8, Canada

New Years Eve Party

 Wed, 31 Dec at 06:00 pm Windsor, Ontario, Canada

Classic Elton in Windsor

 Thu, 22 Jan at 07:30 pm The Chrysler Theatre

🎺 A Christmas Celebration in Windsor ✨ with the Academy Brass Quintet ✨

 Sat, 20 Dec at 04:00 pm MacKenzie Hall

Tea Leaf Readings Afternoon Tea Party

 Sun, 14 Dec at 11:00 am 1295 Ottawa Street, Windsor, ON, Canada

Sloan in Windsor

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

Parking Brantford Bulldogs at Windsor Spitfires

 Sun, 11 Jan at 09:05 pm WFCU Centre

Sarnia Sting at Windsor Spitfires at WFCU Centre

 Sun, 01 Feb at 07:00 pm WFCU Centre

NEW YEARS EVE !! WINDSOR YACHT CLUB " PRIVATE EVENT ""

 Wed, 31 Dec at 09:00 pm Windsor Yacht Club

Snowed in Comedy Tour- Windsor

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

CROSSFADE

 Fri, 19 Dec at 09:00 pm Phog Lounge CAD 12

Fashion Week Windsor-Essex 2026 Fashion Mixer

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

SHAKEY-An Evening with Neil Young...Almost

 Tue, 13 Jan at 02:00 pm West Windsor Public Library

Windsor M**der Mystery: Death in the Shadows

 Sat, 03 May at 11:00 am Walkerville Jubilee Park CAD 14 to 28

Jim Gaffigan in Windsor

 Fri, 06 Mar at 08:00 pm The Colosseum at Caesars Windsor

Charley Crockett in Windsor

 Sun, 01 Mar at 08:00 pm The Colosseum at Caesars Windsor

Rose City Romance 2026

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

Three Days Grace in Windsor

 Fri, 01 May at 07:30 pm The Colosseum at Caesars Windsor

Parking Peterborough Petes at Windsor Spitfires

 Fri, 27 Feb at 12:05 am WFCU Centre

Parking Flint Firebirds at Windsor Spitfires

 Sat, 24 Jan at 12:05 am WFCU Centre

Fashion Week Windsor-Essex 2026 Original Documentary Movie Night

 Wed, 25 Mar at 06:30 pm Windsor Armouries - School of Creative Arts, University of Windsor CAD 28

Diana Krall in Windsor

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

Ademolu Soccer Skills Training

 Fri, 17 Oct at 06:00 pm Westview Freedom Academy CAD 429

The PURE Academy Annual Holiday Showcase (Lakeshore Wednesday/Thursday/Sunday Classes Show)

 Thu, 18 Dec at 06:00 pm The Chrysler Theatre

SCHOOL PERFORMANCE: A Riverfront Double Feature!

 Fri, 30 Jan at 10:00 am 3200 Woodland Ave, Windsor, ON N9E 1Z5, Canada