Upcoming Events in Windsor - Dec 22 - Dec 28
Looking for something fun to do in Windsor next week? We've rounded up some of the best community events happening from December 22 to December 28, 2025. Whether you're interested in arts and culture, family-friendly activities, or community gatherings, there's something for everyone!
High Tea Tuesdays at Cindy’s
📅 Tuesday, December 23, 2025 ⏰ 12:00 AM - 11:59 PM 📍 Cindy's Home & Garden
Treat yourself to a charming High Tea experience at Cindy’s Home and Garden this Tuesday afternoon.
Jingle Jangle Christmas Show
📅 Tuesday, December 23, 2025 ⏰ 7:00 PM - 8:30 PM 📍 Shadowbox Theatre
Support the Windsor Youth Centre at the fabulous 'Jingle Jangle Christmas Show' at Shadowbox Theatre.
Christmas at the Corner – Kingsville
📅 Wednesday, December 24, 2025 ⏰ 12:30 PM - 1:30 PM 📍 The Clock at Main & Division
Enjoy a festive holiday performance at 'Christmas at the Corner' by The Clock at Main & Division in Kingsville.
W.E. Made It Market at Bright Lights Windsor
📅 Friday, December 26, 2025 ⏰ 12:00 AM - 11:59 PM 📍 Jackson Park
The W.E. Made It Market continues at Bright Lights Windsor! Explore local vendors and enjoy the lights at Jackson Park.
Oysters & Bubbly Class
📅 Saturday, December 27, 2025 ⏰ 5:00 PM - 7:00 PM 📍 CREW: Colchester Ridge Estate Winery
Indulge in an evening of ocean-fresh oysters and sparkling wines at the Oysters & Bubbly Class at CREW Winery.
Concerts by Candlelight – Christmas Classics
📅 Saturday, December 27, 2025 ⏰ 12:00 AM - 11:59 PM 📍 Our Lady of the Assumption Church
Relive your favorite 'Christmas Classics' in a stunning candlelight setting at Our Lady of Assumption Church.
Wolfhead Distillery Tours
📅 Saturday, December 27, 2025 ⏰ 12:00 AM - 11:59 PM 📍 Wolfhead Distillery
Discover the art of distilling with a behind-the-scenes tour at Wolfhead Distillery.
Board Game Sunday
📅 Sunday, December 28, 2025 ⏰ 2:00 PM - 5:00 PM 📍 North 42 Degrees Estate Winery
It's Funday Sunday! Enjoy board games and fine wine at North 42 Degrees Estate Winery.
Jazz Night at The Brewery
📅 Sunday, December 28, 2025 ⏰ 6:00 PM - 9:00 PM 📍 Walkerville Brewery
Relax with silky-smooth live jazz by The Coffee House Combo at Walkerville Brewery's Jazz Night.
Willistead Manor Holiday Tours
📅 Sunday, December 28, 2025 ⏰ 1:00 PM - 4:00 PM 📍 Willistead Manor
Don't miss the chance to see Willistead Manor in its holiday glory. Tours include the Coach House and Friends of Willistead holiday display.
These are just a few of the amazing events happening in Windsor! For a complete list of upcoming events and to stay updated on community happenings, visit our events page. Don't forget to check back regularly as new events are added all the time!