What’s Up YQG: Windsor-Essex charity events and festive activities Dec. 19-21

S'Aints Sleighing Hinger performers in Windsor, Ont. (Source: St. Clair College)

With Christmas just around the corner, there are still many festive events and ways to give this holiday season.

Here’s a look at Windsor-Essex events Dec. 19-21.

S’Aints Christmas Concert

The S’Aints Christmas Concert live on stage for two special performances at the St. Clair College Centre for the Arts, December 20 & 21, 2025, at 8:00 p.m.

For over 13 years, The S’Aints have been rocking the season with purpose, raising more than $600,000 in support of food banks across Windsor-Essex and Chatham-Kent. This year’s concerts will once again benefit a number of local charities, helping to provide essential food support throughout the holidays and into the New Year.

Tickets are sold out to this year’s shows, but monetary donations can be made to the Unemployed Help Centre.

Band Members: Jody Raffoul, Jeff Burrows, Kelly Hoppe, Kelly Howell, Wes Buckley, David Cyrenne, Marty Bak, Liz Robinson, Stephanie Baker, and Jim O’Neill.

Tinseltown Windsor Christmas Popup Bar

Friday Nov. 14 to Wednesday Dec. 31

Don’t miss the Tinseltown Windsor Christmas Popup Bar

Amherstburg River Lights Winter Festival

Saturday Nov. 15 to Sunday Jan. 4

Every night from November 15, 2025 to January 4, 2026, hundreds of customized LED light displays light up the town’s two main parks.

Kingsville Fantasy of Lights

Saturday Nov. 15 to Tuesday Jan. 6

The Fantasy of Lights Festival continues with fun holiday activities from Saturday, November 15, 2025 to the first week of January 2026.

LaSalle Holiday Lights and Heritage Nights

Friday Nov. 21 to Sunday Jan. 4

Visit the dazzling LaSalle Holiday Lights Heritage Nights at the LaSalle Civic Centre

Bright Lights Windsor

Friday Nov. 28 to Wednesday Jan. 7

Join us for Bright Lights Windsor 2025, a spectacular celebration of light, community, and local talent!

Harrow’s 2nd Annual Ugly Christmas Sweater Bar Crawl

Friday Dec. 19

Throw on your loudest, wildest, most wonderfully hideous Christmas sweater and join us for a festive night of laughs, drinks, and full-blown holiday chaos!

Latin Night at North 42 Degrees Estate Winery

Friday Dec. 19 5 pm

This is an intimate, high-vibe night out. Perfect for food lovers, wine fans, and anyone looking for an unforgettable evening.

Wolfhead Distillery Tours

Saturday Dec. 20

Get an exclusive behind-the-scenes look at our den, where we craft award-winning whisky, vodka, and gin.

Concerts by Candlelight – Christmas Classics

Saturday Dec. 20

Candlelight concerts bring the magic of a live, multi-sensory musical experience to awe-inspiring locations like never seen before in Windsor.

LaSalle Holiday Lights Heritage Nights Markets

Saturday Dec. 20 to Sunday Dec. 21

Holiday Lights Heritage Nights Events will be held at the Event Centre at LaSalle Landing.

Holiday Wellness Walk

Saturday Dec. 2010:00 am to 11:00 am

Take a peaceful pause and reset from the holiday rush by joining us for a festive Holiday Wellness Walk

SantaCon Windsor 2025

Saturday Dec. 2012:00 pm to 11:00 pm

1st Annual SantaCon Windsor!

Windsor Express Meet & Greet

Saturday Dec. 201:00 pm to 2:30 pm

Come meet the Windsor Express!

Windsor Symphony Orchestra presents Holiday Pops

Saturday Dec. 20 to Sunday Dec. 21

Join the WSO and vocalist Charlotte Knight for the family-fun holiday tradition: Holiday Pops!

A Heritage Christmas

Saturday Dec. 204:00 pm to 7:30 pm

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

Saturday Dec. 206:00 pm to 9:00 pm

Each holiday season keeps getting busier and busier, but the true meaning of Christmas needs to never fade away.

Harrow Kinsmen Christmas Parade

Saturday Dec. 20 6:00 pm

Harrow Kinsmen Christmas Parade is coming up soon, please find the information below for the parade route and date and time.

Elf Movie Night

Saturday Dec. 20 7:00 pm

Enjoy this holiday classic at Chrysler Theatre!

I’ll Be Home For Transanity! Holiday Drag Show Fundraiser

Saturday Dec. 207:00 pm to 10:00 pm

Save the date and get your tickets for our upcoming holiday themed fundraiser!!

Beer and Cheer at The Brewery

Sunday December 21

Come get in the Holiday spirit at Sandwich Brewing Co!

Breakfast with Santa at Willistead Manor

Sunday Dec. 21 10:00 am

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

Sunday Dec. 2111:00 am to 5:00 pm

Celebrate Local. Embrace the Season. Find the Magic.

Caroling in the Carolinian

Sunday Dec. 2111:00 am to 12:00 pm

Join us this holiday season for a unique caroling experience in the heart of the Carolinian Forest with special guest, Sara Fontaine.

Be A Cookie Artist

Sunday Dec. 21

Be A Cookie Artist: Holiday Cookie Decorating Workshop

A Heritage Christmas

Sunday Dec. 2112:30 pm to 4:00 pm

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!

Buyable Experiences

Willistead Manor Holiday Tours

Sunday Dec. 211:00 pm to 4:00 pm

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

Sunday Dec. 212:00 pm to 5:00 pm

Sundays are the ultimate fundays at North 42 Degrees Estate Winery!

Santa’s Cocoa & Candy Cane Social

Sunday Dec. 213:00 pm to 6:00 pm

Santa’s Cocoa and Candy Cane Social is a cozy, drop-in-style celebration designed for families who want festive fun without the fuss.

Winter Solstice Candle Labyrinth Event featuring Fire Performance from Kobbler Jay

Sunday Dec. 216:00 pm to 9:00 pm

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. Join us for a magical evening as we welcome the return of the sun with a candlelit labyrinth walk, surrounded by the warmth of community and the spirit of giving.