Jimmy Carr: Laughs Funny Tue, 13 Oct at 07:30 pm 8787 McHugh Street, Windsor, ON, Canada, Ontario N8S 0A1 COMEDY
UB40 at The Colosseum at Caesars Windsor Fri, 02 Oct at 08:00 pm The Colosseum at Caesars Windsor CALENDAR
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
Disco & Villians Present: The 10th Annual Rocky Horror Screening & Drag Show (Disco’s 10th Rocky) Fri, 16 Oct at 07:00 pm VillainsBeastro Windsor ENTERTAINMENT
Relive the Music 50s 60s & 70s SHOW - Yes we added 70s Mon, 28 Sep at 07:30 pm Capitol Theatre Windsor ENTERTAINMENT
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
Girl Night on Tour! All-Women LIVE Comedy At Tipsy Toucan (Oct 2nd) Fri, 02 Oct at 08:00 pm The Tipsy Toucan CAD 25 FITNESS
Rocktober with Strike Tyson Sat, 03 Oct at 06:30 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4 MUSIC
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
Halloween Club Crawl Windsor Thu, 29 Oct at 08:30 pm Disco Inferno, Wild Child, Treehouse, GOAT Walkerville CONTESTS
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
Friday Comedy Session LIVE At Tipsy Toucan (Oct 16th) Fri, 16 Oct at 08:00 pm The Tipsy Toucan CAD 15 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
Bite Me, B*tch - A Drag Paint Party Night Fri, 16 Oct at 07:00 pm 1009 Drouillard Rd #2 CAD 34 FITNESS
BIG Motorcity Car, Motorcycle, & Truck Show Sun, 04 Oct at 10:00 am Fogolar Furlan Club of Windsor CAR-SHOWS
Windsor Murder Mystery: Solve the case! Tue, 01 Sep at 12:00 am Walkerville Jubilee Pk, 621 Kildare Rd, Windsor, ON N8Y 3G8, Canada CAD 15 TRIPS-ADVENTURES
STILL GOT IT: Halloween 30+ Disco Inferno Day Party Sat, 24 Oct at 04:00 pm Disco Inferno ENTERTAINMENT
Wines for the World 2026 Fri, 23 Oct at 06:00 pm St. Clair College Centre for the Arts HEALTH-WELLNESS
United Way’s Fourth Annual Charity Golf Tournament Mon, 05 Oct at 10:00 am Beach Grove Golf & Country Club Ltd., Riverside Drive East, Windsor, ON, Canada CHARITIES
The Princess Gala presented by Princess Party Sisters Sat, 03 Oct at 02:00 pm Polish Club Windsor CAD 0 TO 44 PARTIES
HABIBI CLUB WINDSOR Ft DJ EDZ • THU OCT 1• @INFERNO (19+) Thu, 01 Oct at 11:00 pm Disco Inferno Dance Bar CAD 10 TO 15 FITNESS
3rd Annual R.Y.O.T. For Charity Pre-Halloween Bash Sat, 17 Oct at 08:00 pm Meteor CAD 0 TO 12 FITNESS
Analogue October Issue Launch Party + Book Swap Thu, 08 Oct at 05:00 pm WindsorEats Food Hall FREE ENTERTAINMENT
LEGO® Build It. Blast It. Save the Day! at Staples Store 112 Wed, 07 Oct at 05:00 pm Staples Tecumseh Store 112 FREE CONTESTS
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
Gatsby Murder Mystery Dinner Cruise Sat, 24 Oct at 05:00 pm 78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4 ENTERTAINMENT
RAW Evolution: Fashion show + Pop-Up Event Sun, 04 Oct at 06:00 pm 2879 Riverside Dr E CAD 10 TO 44 FITNESS
Wednesday Cruise Night @ Parks & Rec Gastropub Wed, 07 Oct at 07:30 pm 3087 Forest Glade Drive, Windsor, ON, Canada, Ontario N8R 1W6
Leo Dufour LIVE Comedy At Tipsy Toucan (Oct 30th) Fri, 30 Oct at 08:00 pm The Tipsy Toucan CAD 30 FITNESS
Project Polly's Ep Release : A Villain's Masquerade Sat, 31 Oct at 08:00 pm JJ's Roadhouse CAD 23 FITNESS
Opportunity Bridal - Wedding Dress Sale - Windsor Sun, 01 Nov at 09:00 am Giovanni Caboto Club CAD 0 TO 54 FITNESS
A Villain's Masquerade : ProjectPolly's HELL ON EARTH EP Release Show & Costume Contest Sat, 31 Oct at 08:00 pm JJ's formerly Jake's Roadhouse & Blues Joint CONTESTS
Windsor-Essex Christmas Market 2026 - Part 1 Sat, 14 Nov at 12:00 pm THE WFCU CENTRE CHRISTMAS-MARKETS-AND-FAIRS
Mack Flash Trivia - Loose Goose Tue, 29 Sep at 07:00 pm The Loose Goose - Resto Pub and Lounge (Walkerville)
The Grand Opening Sat, 03 Oct at 10:00 am Unit 1- 1519 Wyandotte east, Windsor, ON, Canada, Ontario WORKSHOPS
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
KARAEKŌ - Hi-Fi Karaoke Wed, 14 Oct at 07:00 pm 261 Pelissier St., Windsor, ON, Canada, Ontario N9A 4K2 MUSIC
October Tarot & Book Swap Sat, 10 Oct at 01:00 pm 553 Lincoln Rd., Windsor, ON, Canada, Ontario N8Y 2G6 BUSINESS
United Snakes @ Windsor Sportsman club Dougall location, Nov 28th 7:30pm show time. Sat, 28 Nov at 07:30 pm Windsor Sportsman Club MUSIC
Card Board Game Night Mon, 19 Oct at 05:00 pm 103B - 1501 Howard Ave (Howard and Shepherd), Windsor, ON, Canada, Ontario N8X3T5 ART
Ahren Belisle Live In Windsor ON - 2nd Show Added Sun, 22 Nov at 08:30 pm RockStar Music Hall CAD 39 COMEDY
KORDA AUDITIONS - Clue (2027 Season) Sun, 04 Oct at 02:00 pm 2520 Seminole St, Windsor, ON, Canada, Ontario N8Y 1X4 ART
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
Project Polly Presents : HIPHOP4TOTS CHRISTMAS CRASH-OUT SHOW AND TOY DRIVE Sat, 19 Dec at 06:30 pm JJ's Roadhouse CAD 23 FITNESS
The Boom Shaka Lakas Dinner Show Sat, 20 Feb at 06:00 pm 201 Riverside Dr W, Windsor, ON, Canada PARTIES
Windsor Optimist Youth Band 60th Anniversary Gala Sat, 07 Nov at 05:30 pm Fogolar Furlan Windsor CAD 34 TO 75 FITNESS
Windsor, ON - Masonic Temple Ballroom Fri, 23 Oct at 08:00 pm 986 Ouellette Ave, Windsor, ON N9A 1C6, Canada