What's Happening: Windsor

Willistead Manor Holiday Tours

Date: Wednesday, December 17, 2025
Time: 6:00 pm – 8:00 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

W.E. Made It Market at Bright Lights Windsor

Date: Thursday, December 18, 2025
Time: 5:30 pm – 10:00 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!

Canada's Drag Race Episode 5 Viewing Party

Date: Thursday, December 18, 2025
Time: 7:00 pm – 11:00 pm
Location: The Man's Shop & Barbershop Bar
Summary: Come see dazzling performances and watch EP5 of Canada's Drag Race with Van Goth. Featuring Windsor favs Airress and Angelina Lepore.

Ceramic Keepsake Box Workshop

Date: Thursday, December 18, 2025
Time: 6:00 pm
Location: Sketch Clay + Pottery
Summary: In this workshop Dani will guide you step-by-step through creating your very own ceramic keepsake box.

You’ll learn simple handbuilding techniques to shape, texture, and decorate your box, then finish it off with your own creative touches.

NO EXPERIENCE NEEDED! These pieces always turn out amazing and everyone will leave with something unique and personal.

Stress Reset: Interrupt the Overwhelm

Date: Thursday, December 18, 2025
Time: 6:00 pm – 8:30 pm
Location: Balance Fitness Wellness Studio
Ticket Price: $85.00
Summary: This holiday season, Tranquillou Retreats and Balanced Fitness are coming together to create a space for calm, connection, and healing.

Windsor Spitfires Old Fashion Family Spitsmas Game

Date: Thursday, December 18, 2025
Time: 7:05 pm
Location: WFCU Centre
Summary: Catch two top OHL teams in action as the Spitfires face off against the Greyhounds at the WFCU Centre. Don’t miss the energy, talent, and great hockey.

Holiday Dreams – A Spectacular Holiday Show!

Date: Thursday, December 18, 2025
Time: 8:00 pm – 10:00 pm
Location: The Colosseum at Caesars Windsor
Summary: This high-energy, modern holiday production, blends advanced technology with world-class entertainment.

Annual Reading of Frederick Forsyth’s “The Shepherd”

Date: Friday, December 19, 2025
Time: 6:30 pm – 9:00 pm
Location: Canadian Aviation Museum
Summary: Annual reading of Frederick Forsyth's "The Shepherd"

The Mrs. Kennedys + The Waybacks – Live At Meteor

Date: Friday, December 19, 2025
Time: 7:00 pm – 11:30 pm
Location: Meteor
Summary: A night of live rock music at Meteor featuring The Mrs. Kennedys, The Waybacks, and special guests, supporting Harmony in Action.

Crave By Sarah Kane

Date: Friday, December 19, 2025
Time: 8:00 pm. Doors open at 7:30 pm
Location: The Shadowbox Theatre
Ticket Price: $30
Summary: Post Productions presents Crave by Sarah Kane

London, Christmas 1975. A broken family gathers for the holidays, colliding in a fierce, poetic whirlwind of desire, trauma, and longing – inviting the audience to assemble the shattered fragments of a love story teetering on the edge of obsession and despair.

Crave – Sarah Kane’s intensely personal, tender, bold, and hypnotic drama – is a haunting exploration of love and longing in the face of self-destruction. Before the night is over this family will face the devastation that loneliness, memory, alienation, desire, and hope can wreak on fragile human minds.

Hot As Heck Comedy Tour | Windsor

Date: Friday, December 19, 2025
Time: 8:00 pm – 9:30 pm
Location: Meteor
Summary: Hey Windsor! The Hot As Heck Tour is coming to Meteor Lounge to deliver some BIG LAUGHS! Doors open at 7:30 pm, show starts at 8:00 pm. Please arrive no later 7:45PM to be seated before the show starts.

Featuring: Max Sheldrick, Mitch VK, and Doug Koning

John Acquaviva At Ekō.

Date: Friday, December 19, 2025
Time: 9:00 pm – 2:00 am
Location: 261 Pelissier St
Summary: John Acquaviva returns to ekō! Techno pioneer & label legend. Last show sold out immediately. Grab tickets & arrive early!

Last time he played ekō, the night was an immediate sellout right at 9:00pm. Expect the same energy — and then some.

SantaCon Windsor 2025

Date: Saturday, December 20, 2025
Time: 12:00 pm – 11:00 pm
Location: Ford City
Summary: 1st Annual SantaCon Windsor!

Throw on your Santa suit and join us on Drouillard for a full-day crawl through the bars of Ford City — no set route, no RSVP, just pure festive chaos. Show up in costume and be part of something ridiculously fun.

Bring a gift card donation for Drouillard Place, a local community charity. In return, you’ll get a free pint or cookie at participating bars — thanks to the combined support of Bellwoods Brewery and our Ford City bar fam.

We will also be collecting: Gloves, Hats, and most import Socks.

Wolfhead Distillery Tours

Date: Saturday, December 20, 2025
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.

Windsor Symphony Orchestra presents Holiday Pops

Date: Saturday, December 20, 2025
Time: 2:30 pm & 7:30 pm
Location: Capitol Theatre Windsor
Summary: Join the WSO and vocalist Charlotte Knight for the family-fun holiday tradition: Holiday Pops! Performing “Let it Go” from Disney’s Frozen and Christmas favourites like We Wish You a Merry Christmas, It’s Beginning to Look a Lot Like Christmas, Jingle Bells, and more! This concert features the WSO Chorus, Music Moves Kids, and a special guest in a red suit!

Lasalle Holiday Lights Heritage Nights Markets

Date: Saturday, December 20, 2025
Time: 3:00 pm – 9:00 pm
Location: LaSalle Event Centre
Summary: Holiday Lights Heritage Nights Events will be held at the Event Centre at LaSalle Landing.

A Heritage Christmas

Date: Saturday, December 20, 2025
Time: 4:00 pm – 7:30 pm
Location: Canadian Transportation Museum & Heritage Village
Summary: Meet Santa, Mrs. Claus and other familiar faces, learn about historical holiday traditions, make Christmas crafts and participate in festive activities, browse holiday vendors and enjoy live performances!

Need A Little Christmas – Christmas Concert

Date: Saturday, December 20, 2025
Time: 6:00 pm – 9:00 pm
Location: Bloomsbury House
Ticket Price: $30 - Adults, $20 - Under 12
Summary: Each holiday season keeps getting busier and busier, but the true meaning of Christmas needs to never fade away. Come join Alysia Therrien with Ella Paciocco for this one of a kind Christmas concert experience. We all “Need A Little Christmas” because a little joy goes a long way.

Concerts by Candlelight – Christmas Classics

Date: Saturday, December 20, 2025
Time: 6:30 pm & 8:30 pm
Location: Our Lady of Assumption Church
Summary: Candlelight concerts bring the magic of a live, multi-sensory musical experience to awe-inspiring locations like never seen before in Windsor.

Elf Movie Night

Date: Saturday, December 20, 2025
Time: 7:00 pm
Location: Chrysler Theatre
Summary: Enjoy this holiday classic at Chrysler Theatre!

The S’Aints – Sleighing Hunger

Date: Saturday, December 20, 2025
Time: 8:00 pm
Location: Chrysler Theatre
Summary: Join Us For A Holiday Celebration In Support of Windsor Essex and Chatham Kent Food Banks

Over the last 13 years, The S’Aints have been “sleighing hunger” by raising over $600,000 for food banks in Windsor and Chatham.

As in the past, many local charities in Windsor-Essex and Chatham-Kent will benefit, providing food in the holiday season and into the New Year to those in need.

Breakfast with Santa at Willistead Manor

Date: Sunday, December 21, 2025
Time: 10:00 am
Location: Willistead Manor
Summary: Experience includes breakfast buffet, Santa visit and photo op, and a self-guided mini-tour of Willistead Manor.

Windsor-Essex Christmas Market at Libro Centre

Date: Sunday, December 21, 2025
Time: 11:00 am – 5:00 pm
Location: The Libro Centre
Summary: Celebrate Local. Embrace the Season. Find the Magic.

Be A Cookie Artist

Date: Sunday, December 21, 2025
Time: 12:00 pm
Location: WindsorEats
Summary: Be A Cookie Artist: Holiday Cookie Decorating Workshop

WindsorEats is teaming up with Chelsea & Hope from Kings Bake Shop and Searching Southern Ontario for a festive Be A Maker experience that’s as sweet as it gets! In this 1.5-hour hands-on class, you’ll decorate 10 freshly baked cookies while learning pro tips from one of Windsor’s best bakers.

Your ticket includes a drink of your choice from the WindsorEats menu — cocktail, craft beer, or something cozy — because cookies and drinks are a match made in holiday heaven.

A Heritage Christmas

Date: Sunday, December 21, 2025
Time: 12:30 pm – 4:00 pm
Location: Canadian Transportation Museum & Heritage Village
Summary: Meet Santa, Mrs. Claus and other familiar faces, learn about historical holiday traditions, make Christmas crafts and participate in festive activities, browse holiday vendors and enjoy live performances!

Willistead Manor Holiday Tours

Date: Sunday, December 21, 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 21, 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!

Winter Solstice Candle Labyrinth Event

Date: Sunday, December 21, 2025
Time: 6:00 pm – 9:00 pm
Location: Sprucewood Shores Estate Winery
Summary: On the longest and darkest night of the year, take a moment to pause, reflect, and reconnect. Step away from the holiday rush and into a space of peace, intention, and renewal.

High Tea Tuesdays at Cindy’s

Date: Tuesday, December 23, 2025
Time: 10:30 am – 5:30 pm
Location: Cindy’s Home and Garden
Summary: Step into a little bit of charm every Tuesday afternoon with our High Tea at Cindy’s.

Please call to reserve a table.

Jingle Jangle Christmas Show

Date: Tuesday, December 23, 2025
Time: 7:00 pm – 8:30 pm
Location: Shadowbox Theatre
Summary: A fabulous event raising money and collecting canned goods for the Windsor Youth Centre