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Events & things to do In Windsor, Ontario
Concerts, classes and days out, close to home.
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37 events near Windsor
Dan Duvall: Live at Windsor Laughs
The Tipsy Toucan · Windsor, ON
8:00 p.m. to 10:00 p.m.
Dan Duvall brings his ‘Pretty Good Comedy’ filled with punchy comedy and stories of his past to Windsor for one-night only! Dan Duvall is a Victoria based comedian who has performed across Canada and the US including at Just For Laughs Vancouver, CBC’s LOL and Rifflandia Festival. He’s opened for Shawn Majumder, Brent Butt, Bruce McCulloch, Jon Dore and more. He is also the subject of the CraveTV/HBO Canada…
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Jimmy Carr live at the WFCU Centre
WFCU Centre · Windsor, ON
Time on the event website
Outback Presents and Chambers Touring are proud to announce that global comedy superstar Jimmy Carr is returning to Canada with his biggest national tour ever. The brand-new show, Jimmy Carr: Laughs Funny, will hit an unprecedented 31 cities across the country, a first for an international comedian. The tour will play coast to coast, stopping in these 4 cities in Ontario for the first time: Windsor on October 13,…
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Rose City Dueling Pianos at Walkerville Brewery
Walkerville Brewery · Windsor, ON
7:00 p.m. to 10:00 p.m.
Join us for a night of musical fun with Rose City Dueling Pianos ft. Marc Dorian & Jeremy Coulter on Thursday, October 15th, 2026 at 7PM. Get ready to sing along and request your favorite songs as these talented pianists battle it out on the keys! Grab a drink, gather your friends and enjoy an exciting evening of entertainment at Walkerville Brewery! Taproom + Snack Bar will be open late to satisfy your appetites.
US$15.00 USD
Ben Albert: Live in Windsor
The Tipsy Toucan · Windsor, ON
8:00 p.m. to 9:30 p.m.
Headliner Ben Albert brings his wild night of big laughs to Windsor for some intimate shows. Come watch this rising star! A must-see comedy showcase featuring headliner Ben Albert — one of Canada’s fastest-rising comedians. Known for his sharp wit and fearless stage presence, Ben has performed on the hit podcast Kill Tony and has built a massive following online, earning over 15 million views on TikTok. Join Ben for…
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Fleetwood Mac Mania
Chrysler Theatre · Windsor, ON
8:00 p.m. to 8:00 p.m.
Don’t miss Fleetwood Mac Mania at Chrysler Theatre! Tickets: $42.95+taxes & fees
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Diablerie Vampire Ball
Waters Edge Event Centre · Windsor, ON
Dates vary, check full schedule
Embrace The Night For one unforgettable night, mystery, elegance, and spectacle collide inside a transformed decommissioned church, where the walls echo with music and the shadows come alive. Welcome to the Diablerie Vampire Ball in Windsor, Ontario—a lavish vampire court where gothic opulence meets high-energy live music and the allure of burlesque cabaret. Whether you’re a vampire, witch, werewolf, fae, demon,…
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The Black Keys: The Peaches ‘N Kream Tour
The Colosseum at Caesars Windsor · Windsor, ON
7:30 p.m. to 9:30 p.m.
American rock duo The Black Keys are set to ignite The Colosseum stage on their PEACHES ‘N KREAM tour Formed in Akron, Ohio, over two decades ago, The Black Keys are comprised of singer/guitarist Dan Auerbach and drummer Patrick Carney. The duo has been called “rock royalty” by the Associated Press and “one of the best rock ‘n’ roll bands on the planet” by Uncut. Cutting their teeth playing small clubs, The Black…
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Pride Dirty Bingo
Villians Beastro · Windsor, ON
8:00 p.m. to 8:00 p.m.
Get ready for a night of outrageous laughs, cheeky entertainment, and fabulous prizes at our PRIDE DIRTY BINGO! Join us Thursday, October 22, 2026 at 8:00pm at VILLAIN’s BEASTRO for an adults-only evening where classic bingo gets a playful Pride Fest twist, complete with our gracious hosts Venom Von Snap and B Martini giving you campy commentary, music, and plenty of surprises. Whether you’re coming with friends,…
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Dreamer: The Supertramp Experience
Chrysler Theatre · Windsor, ON
8:00 p.m. to 8:00 p.m.
Dreamer – “The Supertramp Experience” delivers a world-class show that includes authentic instrumentation, including vintage keyboards and live horns. Costume changes in between sets set the stage for a memorable evening of the very best Supertramp songs of all time, that are performed by some of North America’s finest A-List musicians. The accuracy of their renditions both vocally and instrumentally are uncanny. A…
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Alice Cooper – Alice’s Attic Tour
The Colosseum at Caesars Windsor · Windsor, ON
8:00 p.m. to 8:00 p.m.
Shock-rock pioneer Alice Cooper returns to The Colosseum stage at Caesars Windsor.
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Catch Country Star Mitchell Tenpenny on Speed of Light Tour Stop at Caesars Windsor
The Colosseum at Caesars Windsor · Windsor, ON
8:00 p.m. to 8:00 p.m.
Mitchell Tenpenny brings his Speed of Light Tour 2026 to The Colosseum stage for a rowdy night of country on Saturday, November 7 at 8 PM. Multi-Platinum artist Mitchell Tenpenny has seen his career explode over the last few years. Since the release of his debut Number One hit single “Drunk Me” the multi-faceted entertainer, singer, songwriter, producer, and performer has surpassed the one billion streams threshold,…
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Tinseltown Windsor Christmas Popup
Windsor Eats · Windsor, ON
5:00 p.m. to 11:00 p.m.
Tinseltown Windsor is back and just like Kevin’s parents, we’d never leave you Home Alone for the holidays. From November 13 to December 31, 2026, WindsorEats Food Hall is undergoing a complete, floor-to-ceiling holiday transformation. We’re turning up the festive chaos, maxing out the tinsel, and making this year’s pop-up bigger, brighter, and way more over-the-top than ever before. Whether you’ve been good, bad,…
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Ashwyn Singh in Windsor: The Imperfect Ally Tour (Early Show)
The Tipsy Toucan · Windsor, ON
8:00 p.m. to 8:00 p.m.
Get ready for an unforgettable night of comedy as Ashwyn Singh brings the Imperfect Ally tour to Windsor. Imperfect Ally is a sharp, hilarious, and thought-provoking stand-up show about how the most sensitive topics are treated insensitively amongst friends. Through funny stories about family, friendship and sharp observations, the show explores allyship, democracy, second-generation immigrant identity, queerness,…
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FMX World Tour
WFCU Centre · Windsor, ON
2:30 p.m. to 2:30 p.m.
The FMX World Tour is an explosive, full-throttle display of athletic ability from professional freestyle motocross riders who defy gravity. These elite athletes push the limits of physics as they soar through the air, delivering jaw-dropping stunts that combine precision, power, and fearless creativity. You will watch in awe as the high-flying FMX World Tour stars perform incredible tricks such as Superman Seat…
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Super Santa 5K
King’s Navy Yard Park · Amherstburg, ON
5:00 p.m. to 6:00 p.m.
Join nearly 800 Santas Walking, Running and Wheeling Through Historic Amherstburg! Get ready to laugh, cheer and make memories as hundreds of Santas fill the streets of historic Amherstburg for a 5K like no other! Whether you walk, run or wheel using your mobility device, the Super Santa Walk/Run/Wheel is all about joining the fun. Suit up in your very own Santa outfit – provided with your registration! Invite…
From US$35.00 USD
Josh Ross: Later Tonight Tour Live at Caesars Windsor
The Colosseum at Caesars Windsor · Windsor, ON
8:00 p.m. to 8:00 p.m.
The electrifying Josh Ross is set to take The Colosseum stage on his Later Tonight Tour! Josh Ross is one of Canada’s most promising singer-songwriter-performers. On an unconventional path of his own design, Ross pairs a dark, mellow blast of modern country rock with a warm vocal rasp, heart-on his-sleeve writing, and addictive hooks. Pulling influence from Guns N’ Roses and Metallica to country-rock outlaw Steve…
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Lee Brice: Sunriser Tour at Caesars Windsor
The Colosseum at Caesars Windsor · Windsor, ON
8:00 p.m. to 8:00 p.m.
Country star Lee Brice is bringing his Sunriser Tour to The Colosseum stage with special guest Grace Tyler on Thursday, November 19th. With over 12.5 billion career streams, Lee Brice continues to enjoy major success at country radio, digital streaming services, and on the road. He has reached the Number One spot at Country Radio with Platinum-selling “Memory I Don’t Mess With,” which consecutively follows three…
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Santa & The Scrooge!
Shady Acres Retirement Home · Windsor, ON
7:00 p.m. to 9:00 p.m.
When Santa thinks he’s found his long-lost son at Shady Acres Retirement Home in Windsor, he drops everything to leave the North Pole to come find him. But when he kidnaps the old man he THINKS is his son and has him brought back to the North Pole, everything starts to go terribly wrong – because Ben Scrodge HATES Christmas! Meanwhile, Santa is posing as Ben down at Shady Acres and everyone is getting very confused,…
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Dean Brody & The Reklaws "Hometown Heroes" Tour
The Colosseum at Caesars Windsor · Windsor, ON
7:30 p.m.
ALL AGES WELCOME Colosseum Show Night Experience: Arrive an hour before show time to avoid lineups for parking and security process. Late arrival may result in longer wait times and late entrance into the show. RESTRICTED BAG POLICY: Bags that are 17.8 cm X 12.7 cm (7" X 5") or smaller are recommended to expedite security procedures. Bags that are 20.3 cm x 28 cm (8" x 11") or smaller are allowed at the discretion…
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Dean Brody & The Reklaws “Hometown Heroes” Tour at Caesars Windsor
The Colosseum at Caesars Windsor · Windsor, ON
7:30 p.m. to 7:30 p.m.
Canada’s most celebrated artists Dean Brody and The Reklaws are joining forces this fall for their co-headlining Hometown Heroes National Tour. Be there when the tour hits The Colosseum stage for an all ages performance on Friday, November 20th. The tour will bring the two chart-topping acts to stages across the country, delivering a must-see live experience packed with career-defining hits, standout storytelling,…
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Hassan Phills: Live in Windsor
The Tipsy Toucan · Windsor, ON
9:30 p.m. to 11:00 p.m.
The fastest rising standup comedian in Canada, Hassan Phills comes to Windsor with new material and a show that engages the audience. Hassan Phills is one of Canada’s fastest rising comedians, known for his engaging and interactive stand-up shows. Recently featured in Crave’s original series ‘The Office Movers’ and with appearances at Just For Laughs and Moontower Comedy Festival, Hassan has firmly established…
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Ahren Belisle Live In Windsor
Rockstar Music Hall · Windsor, ON
6:00 p.m. to 6:00 p.m.
Kill Tony / America’s Got Talent’s Own AHREN BELISLE Live In Windsor ON Ahren Belisle has skyrocketed onto some of the biggest stages in comedy—despite only performing stand-up for a few short years. He won over millions as a Top 10 Finalist on America’s Got Talent and made an unforgettable debut on the wildly popular podcast Kill Tony, where he’s become a regular fixture. A former software engineer and mental…
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Cirque Musica Holiday Wonderland
The Colosseum at Caesars Windsor · Windsor, ON
8:00 p.m. to 8:00 p.m.
Experience the incredible Cirque Musica Holiday Wonderland live from The Colosseum stage! Cirque Musica Holiday Wonderland is a must-see holiday event to usher in the magic of the season. Igniting joy and wonder, Wonderland is a musical journey that will transport audiences to a magical land far away for a fun-filled, unforgettable holiday-themed show experience. Featuring the talented cast of Cirque Musica,…
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Cirque Musica Holiday Wonderland - VIP Pre-show Tour Add-on
The Colosseum at Caesars Windsor · Windsor, ON
8:00 p.m.
Enjoy a pre-show Back Stage Tour that includes an on-stage tour with cast, photo opportunity, meet & greet, merch item and much more. This is offered as a limited-availability add-on upgrade with ticket purchase at The Colosseum at Caesars Windsor. First come, first served. Purchase your VIP Pre-Show ticket today. Must present proof of purchase for entry.
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