Upcoming Community Events in Windsor - Festivals, Workshops, & Local Activities

Community Events

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Pelee Island Winery Half Marathon

Sports and Fitness

May 30, 2026 at 12:00 AM

Pelee Island Winery

Run Canadaâs most southern half-marathon on beautiful Pelee Island, finishing at the Pelee Island Winery.

Frank and Cos: Live in Your Neighbourhood

Arts and Entertainment

May 30, 2026 at 8:00 PM

Chrysler Theatre

Frank and Cos in your “neighbourhood” for an unforgettable night of laughter as Frank Spadone and Cosimo Tucci bring their hilarious sketches to life, live and in-person.

Board Game Sunday

by North 42 Degrees Estate Winery & Bistro 42

Other Event

May 31, 2026 at 2:00 PM

North 42 Degrees Estate Winery

End your month with fun and games at North 42 Degrees Estate Winery's Board Game Sunday.

Phogheads Comedy Showcase

Arts and Entertainment

Jun 02, 2026 at 8:30 PM

Phog Lounge

Looking for something to do Tuesday night? Skip the scrolling and come laugh.

Trivia Night at Manchester Bar

Arts and Entertainment

Jun 04, 2026 at 7:00 PM

The Manchester Bar

Join your host, BRN Trivia, at The Manchester Bar every Thursday at 7pm for free trivia with prizes for the winning teams.

Phogheads Comedy Showcase

Arts and Entertainment

Jun 09, 2026 at 8:30 PM

Phog Lounge

Looking for something to do Tuesday night? Skip the scrolling and come laugh.

Trivia Night at Manchester Bar

Arts and Entertainment

Jun 11, 2026 at 7:00 PM

The Manchester Bar

Join your host, BRN Trivia, at The Manchester Bar every Thursday at 7pm for free trivia with prizes for the winning teams.

Ride the Cyclone at Kordazone Theatre

by Kordazone Theatre

Arts and Entertainment

Jun 12, 2026 - Jun 14, 2026 at 12:00 AM

KordaZone Theater

In this hilarious and outlandish story, the lives of six teenagers from a Canadian chamber choir are cut short in a freak accident aboard a roller coaster.