Bert Kreischer at The Colosseum at Caesars Windsor Thu, 01 Oct at 08:00 pm The Colosseum at Caesars Windsor TRIPS-ADVENTURES
Jimmy Carr: Laughs Funny Tue, 13 Oct at 07:30 pm 8787 McHugh Street, Windsor, ON, Canada, Ontario N8S 0A1 COMEDY
Experience Windsor Free Event Series Tue, 14 Jul 350 City Hall Square West, Windsor, ON, Canada, Ontario N9A 6S1 SPORTS
Whisky Weekend - October 3rd, 2026 Sat, 03 Oct at 11:00 am J.P. Wiser's Experience CAD 10 TO 125 FITNESS
Canadian Famous Comedy Tour LIVE at The Tipsy Toucan (Oct 3rd) Sat, 03 Oct at 08:00 pm The Tipsy Toucan CAD 28 FITNESS
Whisky Weekend Kickoff Masterclass - October 2nd, 2026 Fri, 02 Oct at 07:00 pm J.P. Wiser's Experience CAD 99 FOOD-DRINKS
Relive the Music 50s 60s & 70s SHOW - Yes we added 70s Mon, 28 Sep at 07:30 pm Capitol Theatre Windsor ENTERTAINMENT
Rocktober with Strike Tyson Sat, 03 Oct at 06:30 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4 MUSIC
The Fright Crawl | Windsor's Hottest Halloween Bar Crawl 2026 | Fri, Oct 30 Fri, 30 Oct at 07:30 pm The Thirsty Butler CAD 9 TO 80 FITNESS
Sweet Beats - 30th Anniversary featuring Terrence Parker Sat, 03 Oct at 10:00 pm 839 Erie St E CAD 23 TO 34 ENTERTAINMENT
Hannah Osborne LIVE Comedy At Tipsy Toucan (Oct 10th) Sat, 10 Oct at 08:00 pm The Tipsy Toucan CAD 25 FITNESS
The Fright Crawl | Windsor's #1 Halloween Bar Crawl 2026 | Sat, Oct 31 Sat, 31 Oct at 07:30 pm Bourbon Tap & Grill CAD 9 TO 92 FITNESS
The Australian Bee Gees Show - A Tribute to the Bee Gees Fri, 02 Oct at 07:30 pm The Chrysler Theatre ENTERTAINMENT
Next Stop Comedy at The Lion's Head Tavern! - Windsor, ON Fri, 27 Feb at 08:00 pm Lion's Head Tavern USD 28 FITNESS
Candlelight: Queen vs. ABBA Fri, 30 Oct at 08:45 pm Water's Edge Event Centre CAD 23 TO 76 ENTERTAINMENT
M**der at Walkerville Brewery: A Stand-Up Comedy M**der Mystery Sat, 17 Oct at 08:00 pm Walkerville Brewery CAD 30 TO 44 FITNESS
James Cummins LIVE Comedy At Tipsy Toucan (Sep 26th) Sat, 26 Sep at 08:00 pm The Tipsy Toucan CAD 25 FITNESS
Cruise for a Cause Sat, 26 Sep at 06:00 pm 78 Riverside Dr W, Windsor, Ontario, CA, N9A 0A3 NONPROFIT
Whisky Weekend - October 4th, 2026 Sun, 04 Oct at 11:00 am J.P. Wiser's Experience CAD 10 TO 125 FITNESS
The Fright Crawl | Windsor Halloween Day Bar Crawl 2026 | Sat, Oct 31 Sat, 31 Oct at 01:00 pm TBA CAD 9 TO 80 FITNESS
Dan Duvall: Live at Windsor Laughs Mon, 12 Oct at 08:00 pm Windsor Laughs Comedy Club at The Tipsy Toucan CAD 17 TO 23 FITNESS
2-Minutes To Turkey - Windsor Stand-Up Comedy Contest Fri, 09 Oct at 08:00 pm Windsor Laughs Comedy Club at The Tipsy Toucan CAD 18 TO 23 COMEDY
BIG Motorcity Car, Motorcycle, & Truck Show Sun, 04 Oct at 10:00 am Fogolar Furlan Club of Windsor CAR-SHOWS
Jeremy Porter and The Tucos and The Ford City Ramblers live in Windsor! Sat, 03 Oct at 09:00 pm Phog Lounge
TUSHITA - BOLLYWOOD WORKSHOP IN WINDSOR Sun, 27 Sep at 05:00 pm Industry Dance Co. CAD 25 TO 60 FESTIVALS
Sunset Dinner Cruise Sat, 10 Oct at 06:00 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4 FOOD-DRINKS
The Princess Gala presented by Princess Party Sisters Sat, 03 Oct at 02:00 pm Polish Club Windsor CAD 0 TO 44 PARTIES
Lee Brice at The Colosseum at Caesars Windsor Thu, 19 Nov at 08:00 pm The Colosseum at Caesars Windsor
STILL GOT IT: Halloween 30+ Disco Inferno Day Party Sat, 24 Oct at 04:00 pm Disco Inferno ENTERTAINMENT
Ron Josol LIVE Comedy At Tipsy Toucan (Nov 7th) Sat, 07 Nov at 08:00 pm The Tipsy Toucan CAD 30 COMEDY
WINDSOR SINGLES, Stand up comedy and matchmaking Fri, 16 Oct at 07:00 pm 138 University Ave W CAD 7 TO 23 COMEDY
3rd Annual R.Y.O.T. For Charity Pre-Halloween Bash Sat, 17 Oct at 08:00 pm Meteor CAD 0 TO 12 FITNESS
Funnel Fest/Coach & Horses Reunion: Devilz By Definition Georgie Von Porgie Disco Assault Piesucker Fri, 25 Sep at 08:00 pm Dominion House Tavern (The DH) ENTERTAINMENT
Analogue October Issue Launch Party + Book Swap Thu, 08 Oct at 05:00 pm WindsorEats Food Hall FREE ENTERTAINMENT
Dean Brody at The Colosseum at Caesars Windsor Fri, 20 Nov at 07:30 pm The Colosseum at Caesars Windsor TRIPS-ADVENTURES
Joel Plaskett at The Temple Ballroom Fri, 23 Oct at 07:00 pm Windsor Masonic Temple 100 year Anniversary ART
Gatsby Murder Mystery Dinner Cruise Sat, 24 Oct at 05:00 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4 ENTERTAINMENT
Candlelight: Halloween Classics Fri, 30 Oct at 06:30 pm Water's Edge Event Centre CAD 27 TO 67 ENTERTAINMENT
Halloween Edition - M**der at Water's Edge: Stand-Up Comedy M**der Mystery Sat, 24 Oct at 08:00 pm Water's Edge Event Centre CAD 40 TO 50 COMEDY
Project Polly's Ep Release : A Villain's Masquerade Sat, 31 Oct at 08:00 pm JJ's Roadhouse CAD 23 FITNESS
Ben Albert: Live in Windsor Sat, 17 Oct at 08:00 pm The Tipsy Toucan - Public House CAD 22 TO 27 FITNESS
Opportunity Bridal - Wedding Dress Sale - Windsor Sun, 01 Nov at 09:00 am Giovanni Caboto Club CAD 0 TO 54 FITNESS
2 Days Certified ScrumMaster (CSM) Training in Windsor, ON Sat, 26 Sep 377 Riverside Dr E USD 583 WORKSHOPS
Windsor-Essex Christmas Market 2026 - Part 1 Sat, 14 Nov at 12:00 pm THE WFCU CENTRE CHRISTMAS-MARKETS-AND-FAIRS
Hassan Phills: Live in Windsor Fri, 20 Nov at 09:30 pm Windsor Laughs Comedy Club at The Tipsy Toucan CAD 33 TO 39 FITNESS
Ella Horwedel LIVE Comedy At Tipsy Toucan (Nov 28th) Sat, 28 Nov at 08:00 pm The Tipsy Toucan CAD 25 FITNESS
Hocus Pocus, Diamond Art & Matcha Movie Night ✨ Wed, 14 Oct at 06:30 pm 1009 Drouillard Rd #2 CAD 44 TO 50 FITNESS
The Vampire Diaries Trivia & Paint Night Thu, 15 Oct at 06:30 pm 1009 Drouillard Rd #2 CAD 50 TO 55 FITNESS
The Bridge: DETROIT Edition LIVE Comedy At Tipsy Toucan (Nov 14th) Sat, 14 Nov at 08:00 pm The Tipsy Toucan CAD 25 FITNESS
Changing Seasons with Clear Acetate Film – Kids Art Class Sat, 26 Sep at 01:00 pm Expressive Brush Art Studio CAD 17 ART
Candlelight: Christmas Carols on Strings Sat, 19 Dec at 06:30 pm Our Lady of the Assumption Church CAD 30 TO 76 ENTERTAINMENT
Candlelight: Tribute to Michael Jackson Fri, 11 Dec at 06:30 pm Water's Edge Event Centre CAD 20 TO 56 ENTERTAINMENT
An Afternoon with UFC Legend Mark Coleman: Screening & Live Q&A Sun, 27 Sep at 03:30 pm Riverside Sportsmen Club CAD 39 TO 108 FITNESS
Halloween Costume & Craft Party: Adopt-a-furry friend Sun, 25 Oct at 11:00 am 1009 Drouillard Rd #2 CAD 23 TO 39 COSTUME-PARTIES
💥🎤🎶Ultimate Karaoke - Alternate Saturdays 🎶🎤💥 Sat, 08 Aug JJ's formerly Jake's Roadhouse & Blues Joint MUSIC
Josh Adams LIVE Comedy At Tipsy Toucan (Dec 12th) Sat, 12 Dec at 08:00 pm The Tipsy Toucan CAD 25 FITNESS
KORDA AUDITIONS - Clue (2027 Season) Sun, 04 Oct at 02:00 pm 2520 Seminole St, Windsor, ON, Canada, Ontario N8Y 1X4 ART
United Snakes @ Windsor Sportsman club Dougall location, Nov 28th 7:30pm show time. Sat, 28 Nov at 07:30 pm Windsor Sportsman Club MUSIC
Still Standing - Some How.. Comedy Tour.. Windsor Sat, 07 Nov at 07:00 pm 460 Erie St E CAD 25 TO 34 FITNESS
Ahren Belisle Live In Windsor ON - 2nd Show Added Sun, 22 Nov at 08:30 pm RockStar Music Hall CAD 39 COMEDY
MefLab Muzik Presents: The Berzerk - Demon Vs. Psycho Album Release Party. Sat, 24 Oct at 09:00 pm 44 University Ave W CAD 12 PARTIES
A Colorful Christmas - Windsor - 2026 - Christian Concert Tour Fri, 04 Dec at 07:00 pm Windsor Christian Fellowship CAD 17 TO 38 MUSIC
HIPHOP&HEELS : SECOND ANNUAL INTERNATIONAL WOMENS DAY EVENT Sat, 06 Mar at 07:00 pm The Well Windsor CAD 20 ENTERTAINMENT
The Boom Shaka Lakas Dinner Show Sat, 20 Feb at 06:00 pm 201 Riverside Dr W, Windsor, ON, Canada PARTIES