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
UB40 at The Colosseum at Caesars Windsor Fri, 02 Oct at 08:00 pm The Colosseum at Caesars Windsor CALENDAR
UB40 | Caesars Ticket + Hotel Packagess Fri, 02 Oct at 08:00 pm The Colosseum at Caesars Windsor MUSIC
The Black Keys at The Colosseum at Caesars Windsor Sun, 18 Oct at 07:30 pm The Colosseum at Caesars Windsor TRIPS-ADVENTURES
Twisted Sister at The Colosseum at Caesars Windsor Sat, 10 Oct at 08:00 pm The Colosseum at Caesars Windsor
ABBA vs Queen by Candlelight | Glenwood United Church | Windsor Sat, 03 Oct at 07:00 pm Glenwood United Church CAD 20 TO 65 FITNESS
The Black Keys with Jeremie Albino (19+) Sun, 18 Oct at 07:30 pm The Colosseum at Caesars Windsor CALENDAR
Twisted Sister with Sebastian Bach on vocals (19+) Sat, 10 Oct at 08:00 pm The Colosseum at Caesars Windsor TRIPS-ADVENTURES
The Black Keys: PEACHES 'N KREAM | Caesars Ticket + Hotel Packages Sun, 18 Oct at 07:30 pm The Colosseum at Caesars Windsor MUSIC
Whisky Weekend - October 3rd, 2026 Sat, 03 Oct at 11:00 am J.P. Wiser's Experience CAD 10 TO 125 FITNESS
Windsor Zombie Walk & Parade 2026 Sat, 03 Oct at 05:00 pm Ouellette Avenue, Windsor, Ontario NONPROFIT
Whiskey Myers at The Colosseum at Caesars Windsor Thu, 08 Oct at 07:00 pm The Colosseum at Caesars Windsor
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
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
TWISTED SISTER Featuring Sebastian Bach on Lead Vocals Sat, 10 Oct at 08:00 pm The Colosseum at Caesars Windsor MUSIC
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
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
Whisky Weekend - October 4th, 2026 Sun, 04 Oct at 11:00 am J.P. Wiser's Experience CAD 10 TO 125 FITNESS
Taylor Swift Trivia and Charm Bracelet Night Tue, 06 Oct at 06:30 pm 1009 Drouillard Rd #2 CAD 39 TO 44 TAYLOR-SWIFT
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
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
Bite Me, B*tch - A Drag Paint Party Night Fri, 16 Oct at 07:00 pm 1009 Drouillard Rd #2 CAD 34 FITNESS
Starry Night, inspired by Van Gogh Painting Class for Adults & Teens Fri, 24 Feb at 07:30 pm Expressive Brush Art Studio CAD 48 FITNESS
Windsor Essex County's 5th Annual Bathukamma Festival - 2026 Sat, 10 Oct at 07:00 pm Hindu Temple and Cultural Center of Windsor CAD 15 FITNESS
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
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
Wines for the World 2026 Fri, 23 Oct at 06:00 pm St. Clair College Centre for the Arts HEALTH-WELLNESS
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
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
Lee Brice at The Colosseum at Caesars Windsor Thu, 19 Nov at 08:00 pm The Colosseum at Caesars Windsor
Gilmore Girls Paint & Trivia Night Thu, 17 Sep at 06:30 pm 1009 Drouillard Rd #2 CAD 50 TO 55 DRAWING-PAINTING
STILL GOT IT: Halloween 30+ Disco Inferno Day Party Sat, 24 Oct at 04:00 pm Disco Inferno ENTERTAINMENT
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
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
Warehouse Scrubs Sale – Windsor, ON– 1 Day Only Mon, 28 Sep at 10:00 am Holiday Inn & Suites Windsor (Ambassador Bridge) by IHG FREE 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
Dean Brody at The Colosseum at Caesars Windsor Fri, 20 Nov at 07:30 pm The Colosseum at Caesars Windsor TRIPS-ADVENTURES
Mitchell Tenpenny at The Colosseum at Caesars Windsor Sat, 07 Nov at 08:00 pm The Colosseum at Caesars Windsor
Joel Plaskett at The Temple Ballroom Fri, 23 Oct at 07:00 pm Windsor Masonic Temple 100 year Anniversary ART
Candlelight: Halloween Classics | Windsor Fri, 30 Oct at 01:30 pm Water's Edge Event Centre, Private tours by appointment only, 2879 Riverside Drive East, Windsor ENTERTAINMENT
Opening Weekend: From Paris to Madrid Sat, 26 Sep at 07:30 pm 121 University Avenue, West, Windsor, ON, Canada, Ontario N9A 5P4 MUSIC