The holiday season can be a bit of a blur between shopping for gifts, visiting family, and hosting delicious dinners. We’ve gathered a list of some fun events to break up some of that time to take in some art, share a laugh and make new friends in the city.
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Toronto History Museums: Illumination
The city is hosting a number of illuminating workshops and events this winter! From a comedy night at Todmorden Mills to Winter Solstice tea at Montgomery’s Inn, gingerbread workshops in Fort York, and cozy Sundays at Spadina Museum, there’s tons of family friendly events for everyone to indulge in. More Info
When: Various dates
Where: Various locations
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Second City Holiday Shows
Give the gift of laughter this holiday season with Second City’s selection of holiday shows! Improvised holiday hijinks in their Naughty, Nice & Undecided shows and seasonal sketches in their Make It Reindeer shows are what’s in store for those who love to laugh. More Info
When: November 20-December 31
Where: Second City
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Winterfest Toronto
Harbourfront Centre is debuting this new holiday market. With sparkling lights, tasty food, mulled wine and hand-crafted, one-of-a- kind gifts, this is a great addition to the city’s must-visit holiday stops! It will also feature a live tree lighting event, a Scandinavian- inspired indoor/outdoor bar and s’mores over open-air fire pits! More Info
When: November 29-January 5
Where: Harbourfront Centre
Courtesy of Window Wonderland
Window Wonderland
This winter, The Junction is transforming into a free outdoor gallery, featuring 20 spectacular augmented reality (AR) window installations and ten murals, all designed by local and international artists. Stretching from Quebec Avenue to Indian Grove, there’s tons to take in with friends and family. More Info
When: November 29-January 31
Where: The Junction
Courtesy of City of Toronto
Cavalcade of Lights
Toronto’s Cavalcade of Lights returns this year at Nathan Philips Square. The opening night, inspired by winter solstice celebrations, includes performances by Zaynab Wilson MoZayic, Zero Gravity Circus and more! The skating rink will also be open for public skating, as well as a skating showcase. And of course, the lighting of the Christmas tree & Nathan Phillips Square! More Info
When: November 30-January 7
Where: Nathan Phillips Square
Courtesy of Fleurs De Villes Noël
Fleurs de Villes Noël
The 3rd annual Fleurs de Villes Noël floral trail returns to the Bloor-Yorkville neighbourhood once again to celebrate the holiday season! These festive floral installations, inspired by beloved holiday songs and created by local floral artists, will inspire you this gift-giving season. The installation also includes pop-up flower markets, for anyone looking to spruce up their holiday decorating. More Info
When: December 4-8
Where: Yorkville
Yonge-Dundas Square Winter Glow – Toronto, 2023 © Brock Wunder
Winter Glow
This festive event will be bringing dazzling lights, carnival rides, games, and entertainment to the downtown core! With a 45ft tall Ferris Wheel, the Great Canadian Carousel and Teacups, kids and adults alike will have lots of fun. Visitors can also donate and receiveto get a yellow ribbon to write a message to a loved one and attach it to the Tree of Rememberance. More Info
When: December 5-22
Where: Sankofa Square (formerly Yonge- & Dundas)
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Casa Loma Holiday Lights Tour
Casa Loma will be lit up for the holidays! This season, visitors are invited to wander through a dazzling lighting display in the gardens and tunnels, all decorated for the holidays, in this self-guided walking tour. The castle workshop will also be open, for any kids (or adults) wanting to visit Santa before Christmas. More Info
When: December 5-January 4
Where: Casa Loma
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A Burlesque-Mas Carol
The story of Scrooge told through the enchanting art of burlesque?! Yes, a Burlesque-Mas Carol is just that! With playful parody and saucy surprises, this one-of-a-kind show is whimsical, glamorous, seductive and heartwarming. This is a can’t miss for anyone looking for a unique way to kick off their holiday season. More Info
When: December 6-7
Where: The Painted Lady
Photo by Karolina Kuras. Courtesy of The National Ballet of Canada.
The Nutcracker
The classic holiday ballet is back in Toronto. The National Ballet of Canada invites audiences to experience the wonder of the holidays with The Nutcracker, a spectacular family production. Set to Tchaikovsky’s famous score, don’t miss this opportunity to visit the fantastic land of the Sugar Plum Fairy! More Info
When: December 6-31
Where: Four Seasons Centre for the Performing Arts
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Krampus Ball
If you’re looking for a Christmas alternative, look no further than the Krampus Ball. Celebrate the 12th year of this festival marking the iconic Central and Eastern European folktale. This seasonal costume party is more about horns than holly, with Krampus-inspired costumes encouraged! More Info
When: December 7
Where: Opera House
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Bach-Humbug
For those who aren’t into the holiday spirit, The Redwood Theatre is hosting this cathartic concert, featuring music carefully curated to satisfy all seasonal skepticism, including The Grinch, Blue Christmas, and more! And don’t forget your non-perishables, as they are hosting a food drive to benefit the Daily Bread food bank. More Info
When: December 8
Where: The Redwood Theatre
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Gay AF Christmas Spectacular
The 5th annual Queer Christmas tradition described as “funny, heartwarming” returns to the city for even more laughs! Featuring performers such as Martha Chaves, Sarah Ashby and Shaska DC, and a sexy Santa, who will be there to find out who’s been naughty, it’s guaranteed to be quite nice. More Info
When: December 11-12
Where: Comedy Bar West
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Holiday! An Improvised Musical
Holiday! An Improvised Musical is taking its comedic improvisational stylings to this holiday season! Based on suggestions from the audience, the cast creates a series of improvised vignettes and songs exploring themes of love, relationships, work and the true meaning of the winter holiday season. More Info
When: December 11-22
Where: Factory Theatre
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Winter Blooms: Circus at the Garden
Enjoy an intimate and interactive high-flying circus show featuring aerial silks, acrobatics, strength, artistry and humour. Suitable for friends and families alike, this performance will take you on a magical journey as the garden awakens from its gentle winter slumber. Audience members are invited to meet the cast after the show. More Info
When: December 20-22
Where: Toronto Botanical Garden
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