Date On Purpose: The Intentional Dating Experience (Ages 50–65+)

Date: Wednesday, February 18, 2026
Time: 6:30 pm – 8:30 pm
Location: Wineology
Summary: Date on Purpose an IRL event for intentional singles who want to show up like & connect like humans again… and on purpose. Humans who want real conversation. Real presence. Real effort and absolutely no tolerance for guessing games. They want the good wholesome stuff…and the possibility of meeting someone they want to see again.

MCC Create Your Career Day

Date: Thursday, February 19, 2026
Time: 9:30 am – 2:30 pm
Location: Capitol Theatre Windsor
Summary: Welcome to MCC Create Your Career Day!

Join us for this unique opportunity to network with community partners and learn how to achieve your career goals. Afterwards, we invite you to relax and enjoy the movie "The Pursuit of Happyness".Employment and career development can be stressful, not for this event. Meet, greet and get to know more about several careers.

OnStage: Serenade for Strings

Date: Thursday, February 19, 2026
Time: 7:30 pm – 8:30 pm
Location: Capitol Theatre Windsor
Summary: Sit where the musicians sit… onstage!

Hannah Berner: None Of Your Business Tour

Date: Thursday, February 19, 2026
Time: 8:00 pm – 10:00 pm
Location: The Colosseum at Caesars Windsor
Summary: Catch the hilarious Hannah Berner on her None Of My Business Tour, live from The Colosseum stage!

Café Concert: Serenade for Strings

Date: Friday, February 20, 2026
Time: 11:00 am – 12:00 pm
Location: Capitol Theatre Windsor
Summary: Enjoy your morning coffee on stage with music and the WSO!

Dueling Pianos

Date: Friday, February 20, 2026
Time: 7:00 pm – 10:00 pm
Location: Walkerville Brewery
Summary: Join us on Thursday, February 19th at Walkerville Brewery for Rose City Dueling Pianos ft. Mark Calcott & Frank McGlynn

Galentines In Jammies For Tabitha's Tribe

Date: Saturday, February 21, 2026
Time: 9:00 am – 11:00 am
Location: Mackenzie Hall Cultural Centre
Summary: Tabitha's tribe; The Sisters' Fellowship of RCCG Restoration House is celebrating love and sisterhood under the banner of Christ❤️

Henry's Windsor On-Camera Flash Workshop

Date: Saturday, February 21, 2026
Time: 1:00 pm – 2:00 pm
Location: 3155 Howard Ave
Summary: Curious about the magic of on-camera flash? Join us!

Wolfhead Distillery Tours

Date: Saturday, February 21, 2026
Time: 1:00 pm & 3:00 pm
Location: Wolfhead Distillery
Summary: Get an exclusive behind-the-scenes look at our den, where we craft award-winning whisky, vodka, and gin.

Intro To Inversions & Arm Balances

Date: Saturday, February 21, 2026
Time: 1:30 pm – 3:30 pm
Location: MOVATI Athletic Windsor
Summary: Intro to Inversions & Arm Balances builds strength, confidence, and safety with smart alignment and step-by-step progressions for all levels

It’s 5 O’Clock Somewhere Fest

Date: Sunday, February 22, 2026
Time: 1:00 pm – 6:30 pm
Location: Phog Lounge
Summary: You asked (indirectly), and we’re answering (directly). A daytime, all ages music fest, full of a multitude of music genres and volumes!

Board Game Sunday

Date: Sunday, February 22, 2026
Time: 2:00 pm – 5:00 pm
Location: North 42 Degrees Estate Winery
Summary: Sundays are the ultimate fundays at North 42 Degrees Estate Winery!

Windsor Spitfires V.S Flint Firebirds

Date: Sunday, February 22, 2026
Time: 4:05 pm
Location: WFCU Centre
Summary: Catch two top OHL teams in action as the Spitfires face off against the Firebirds at the WFCU Centre. Don’t miss the energy, talent, and great hockey.

Laugh-A-Rita Comedy Night At Treehouse!

Date: Sunday, February 22, 2026
Time: 5:00 pm – 6:00 pm
Location: Treehouse
Summary: Laugh, sip, repeat. On National Margarita Day, Treehouse hosts a killer comedy show with top Latin comedians from Windsor and Detroit!

Speed Dating In Windsor

Date: Sunday, February 22, 2026
Time: 5:30 pm – 7:30 pm
Location: Devonshire Mall
Summary: We're back for another Speed Dating Event at the Canadian Brewhouse in Devonshire Mall for ages 24-45.

Triple X Oh!

Date: Sunday, February 22, 2026
Time: 7:00 pm – 10:00 pm
Location: Chapter Two Brewing Company
Summary: Join your hosts from the House of Cures Saturday February 21st for Windsor-Essex's premier adult drag show - TRIPLE X OH!

Hershawn Arora Live Comedy At Tipsy Toucan (Feb 21St)

Date: Sunday, February 22, 2026
Time: 8:00 pm – 9:30 pm
Location: The Tipsy Toucan
Summary: Toronto’s rising comedy star Hershawn Arora brings his Short King Tour to Windsor!

Expendable Youth Returns To The Cherry

Date: Sunday, February 22, 2026
Time: 10:00 pm – 11:59 pm
Location: The Cherry Rock Lounge
Summary: Expendable Youth is back at The Cherry for an epic night of Pop Punk and Alternative Hits you know and love! WSG Taya Fanara!

Windsor Express vs Sudbury Five

Date: Tuesday, February 24, 2026
Time: 7:00 pm
Location: WFCU Centre
Summary: BSL Basketball