What's Happening: Windsor

W.E. Made It Market at Bright Lights Windsor

Date: Friday, December 26, 2025
Time: 5:30 pm – 11:00 pm
Location: Jackson Park
Summary: Experience the magic of the WE Made It: Holiday Market every Thursday through Sunday with a full selection of local vendors. Can't make it on the weekend? You can find select vendors onsite during the week!

Wolfhead Distillery Tours

Date: Saturday, December 27, 2025
Time: 1:00 pm & 3:00 pm
Location: Wolfhead Distillery
Ticket Price: $20 per person, $10 for minors
Summary: Get an exclusive behind-the-scenes look at our den, where we craft award-winning whisky, vodka, and gin.

Dave Merheje-Christmas Edition Live Comedy At Tipsy Toucan (Dec 27Th)

Date: Saturday, December 27, 2025
Time: 3:00 pm – 4:30 pm
Location: The Tipsy Toucan
Ticket Price: $25
Summary: SPECIAL EVENT: Windsor’s own Juno Award winner Dave Merheje returns home for the holidays—one night only!

Definite Leppard - Live At The Cherry

Date: Saturday, December 27, 2025
Time: 4:00 pm – 9:00 pm
Location: The Cherry Rock Lounge
Ticket Price: $17.31
Summary: Definite Leppard takes us back to the glory days of arena rock, with a tribute to a monster band of the era, Def Leppard!

Concerts by Candlelight – Christmas Classics

Date: Saturday, December 27, 2025
Time: 6:30 pm & 8:30 pm
Location: Our Lady of Assumption Church
Ticket Price: From $37.50
Summary: Candlelight concerts bring the magic of a live, multi-sensory musical experience to awe-inspiring locations like never seen before in Windsor.

Rise On The Mat: Ashtanga Yoga Experience For Women Reclaiming Their Power

Date: Sunday, December 28, 2025
Time: 7:30 am – 9:00 am
Location: Breathe Pilates and Yoga Studio
Summary: Free Ashtanga yoga workshop for women reclaiming their power. Sun, Dec. 28 at 7:30AM | Breathe Yoga Windsor. Come rise on the mat. ‍♀️✨

If you’re a woman navigating life and ready to embody your next level of authentic power so that you can feel stronger, more relaxed and regulated no matter what is going on around you then this workshop is for you.

Willistead Manor Holiday Tours

Date: Sunday, December 28, 2025
Time: 1:00 pm – 4:00 pm
Location: Willistead Manor
Summary: Experience includes tours of Willistead Manor all decked out in its holiday finest, tours of the new Coach House Historical Exhibition, and access to the Friends of Willistead's holiday display

Board Game Sunday

Date: Sunday, December 28, 2025
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!

Cozy Connections Speed Dating | Windsor | Ages 25 To 45 Years

Date: Sunday, December 28, 2025
Time: 5:30 pm – 7:30 pm
Location: Kelseys Original Roadhouse
Ticket Price: $33.28
Summary: Mix, mingle, and spark something new! Join us for an exciting night of Speed Dating in Windsor for singles aged 25 to 45.

Close out the year with a night of real conversations and new connections at our casual and welcoming Speed Dating event for singles ages 25 to 45 in Windsor! Designed for comfort, fun, and authenticity, this event is perfect whether you’re brand new to speed dating or a seasoned social butterfly.