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Events & things to do In Windsor, Ontario
Concerts, classes and days out, close to home.
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14 events near Windsor
WINDSOR SINGLES, Stand up comedy and matchmaking
Meteor · Windsor, ON
7:00 p.m. to 9:00 p.m.
“Laugh. Mingle. Maybe Match.” Looking to laugh and maybe meet someone new? WINDSOR Singles is a one-of-a-kind night that blends stand-up comedy with real-life matchmaking. Kick back with a drink, enjoy a lineup of hilarious comedians, and take part in a fun, low-pressure dating experience designed to spark genuine connections. Whether you’re single and ready to mingle or just in it for the laughs, expect a night…
US$15.00 USD
Standup Comedy at Sidelines Sports Bar & Grill!
Sidelines Sports Bar & Grill · Windsor, ON
8:00 p.m. to 9:30 p.m.
Get ready to laugh at Standup Comedy at Sidelines Sports Bar & Grill! Join us for a hilarious evening filled with jokes, good vibes, live music and great company! It’s the perfect way to unwind and enjoy some live humor right at Sidelines Sports Bar & Grill. Don’t miss out on the fun – bring your friends and let the good times roll!
From US$10.00 USD
Jeff Leeson: Only Gonna Say This Once Comedy Tour
Chrysler Theatre · Windsor, ON
8:00 p.m. to 8:00 p.m.
Internationally touring comedian Jeff Leeson comes to Windsor for a night of live stand up comedy you will never forget! With over 25 years of touring experience and over 100 Million views online, find out why this is definitely one show you absolutely Do Not want to miss! Ages 16+ Tickets: $35+taxes & fees Debit cards cannot be used as a form of online payment. Visa & Mastercard only. No AMEX No refunds or…
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Leo Dufour LIVE Comedy At Tipsy Toucan
The Tipsy Toucan · Windsor, ON
7:30 p.m. to 9:00 p.m.
Leo Dufour, founder of Windsor’s iconic Komedy Korner, returns to the heart of Ottawa Street for one unforgettable night of high-energy laughs, quick wit, and classic storytelling. If you’ve ever seen Leo live, you already know—his shows are a guaranteed good time. If you haven’t? Don’t miss your chance. Venue & Show Info: – Doors Open: 7:30 PM | Show Starts: 8:00 PM – Venue: Located downstairs | 19+ only |…
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Ron Josol LIVE Comedy At Tipsy Toucan
The Tipsy Toucan · Windsor, ON
7:30 p.m. to 9:00 p.m.
Ron Josol is a Canadian-Filipino comedy powerhouse whose razor-sharp wit and global swagger have made him one of the most sought-after stand-up acts on the planet. A true legend of the circuit, Ron has carved out a career that spans continents—headlining sold-out shows from Toronto to Tokyo, Dubai to New York. Not to mention having performed at the prestigious Just for Laughs comedy festival in Montreal a staggering…
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O Christmas Tea: A British Comedy
Chrysler Theatre · Windsor, ON
7:30 p.m. to 9:30 p.m.
Fans of Monty Python, Mr. Bean, and Dr. Seuss… Grab your teacups! Combining British propriety with an unabashed love for the unexpected, London’s 3-time Impresario Award-winning duo steep an outrageously funny and brilliantly inventive show reminiscent of classic British pantos. Rich in wordplay, comic physicality, and cleverly crafted interactive elements, O Christmas Tea is uproarious fun, yet it is the duo’s…
US$26.00 USD
The Bridge: DETROIT Edition LIVE Comedy At Tipsy Toucan
The Tipsy Toucan · Windsor, ON
7:30 p.m. to 9:30 p.m.
Josh Adams is crossing the border with 2 of his funniest friends for his bi-monthly Detroit takeover of the Windsor Laughs Comedy Club! Hailing from Detroit, Michigan, Josh Adams is gearing up to be a comedic heavy hitter. Over the course of his career, Adams has performed in front of all types of audiences from mainstream to urban, and at venues across the country ranging from colleges, to churches, to comedy…
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Ella Horwedel LIVE Comedy At Tipsy Toucan
The Tipsy Toucan · Windsor, ON
7:30 p.m. to 9:00 p.m.
Often described as raunchy, irreverent, and a disappointment by her mother, Ella Horwedel has been an energetic force in the Midwest comedy scene for the past eight years. She has headlined at clubs all over the country, where she explores the difficulties of being a 27-year-old woman through bawdy stories and intimate self-reflection. She has opened for Kyle Kinane, Jordan Jensen, Ron Funches, Beth Stelling, and…
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Josh Adams LIVE Comedy At Tipsy Toucan
The Tipsy Toucan · Windsor, ON
7:30 p.m. to 9:00 p.m.
Hailing from Detroit, Michigan, Josh Adams is gearing up to be a comedic heavy hitter. Over the course of his career, Adams has performed in front of all types of audiences from mainstream to urban, and at venues across the country ranging from colleges, to churches, to comedy clubs. Drawing from his unique perspective as a kid who was born in the hood and grew up in the suburbs, Adams holds his own when performing…
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Bored Teachers Comedy Tour
The Chrysler Theatre · Windsor, ON
7:00 p.m. to 7:00 p.m.
They’ve graded the papers, survived the staff meetings, and lost their last ounce of patience… and now they’re taking it out on stage! Bored Teachers is back with brand-new jokes, bigger laughs, and the most relatable teacher comedy you’ll ever hear. For nearly a decade, Bored Teachers has been the #1 voice of teacher humor—racking up over 1 billion views, amassing 10 million+ followers, and hosting the #1…
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Caroline Rhea & Debra DiGiovanni Comedy Tour
The Chrysler Theatre · Windsor, ON
8:00 p.m. to 8:00 p.m.
Caroline Rhea & Debra DiGiovanni Comedy Night Get ready for a night of sharp wit, fearless storytelling, and nonstop laughs as Canadian comedy powerhouses Caroline Rhea and Debra DiGiovanni take the stage together for an unforgettable evening of stand-up. From television screens to sold-out theatres, these two comedy queens bring their signature styles—quick, clever, and unapologetically honest—for a high-energy…
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Korda Productions Presents DRACULA: A Comedy of Terrors
Kordazone Theatre · Windsor, ON
Dates vary, check full schedule
DRACULA, A COMEDY OF TERRORS is a Bram-new comedy you can really sink your teeth into! Filled with clever wordplay and anything-goes pop culture references, it’s a 90-minute, gender-bending, quick-changing, laugh-out-loud reimagining of the gothic classic, perfect for audiences of all blood types. In the treacherous mountains of Transylvania, a meek English real estate agent takes a harrowing journey to meet a new…
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Korda Productions Presents DRACULA: A Comedy of Terrors
Kordazone Theatre · Windsor, ON
Dates vary, check full schedule
DRACULA, A COMEDY OF TERRORS is a Bram-new comedy you can really sink your teeth into! Filled with clever wordplay and anything-goes pop culture references, it’s a 90-minute, gender-bending, quick-changing, laugh-out-loud reimagining of the gothic classic, perfect for audiences of all blood types. In the treacherous mountains of Transylvania, a meek English real estate agent takes a harrowing journey to meet a new…
See event website for price
Korda Productions Presents DRACULA: A Comedy of Terrors
Kordazone Theatre · Windsor, ON
Dates vary, check full schedule
DRACULA, A COMEDY OF TERRORS is a Bram-new comedy you can really sink your teeth into! Filled with clever wordplay and anything-goes pop culture references, it’s a 90-minute, gender-bending, quick-changing, laugh-out-loud reimagining of the gothic classic, perfect for audiences of all blood types. In the treacherous mountains of Transylvania, a meek English real estate agent takes a harrowing journey to meet a new…
See event website for price