With the holiday season in full swing, Toronto has comedy shows, theatre, markets and more to keep us entertained and get us in the winter mood.

 

 
 
 
 
 
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The Wizard of Oz: The Toto-ly Awesome Family Musical

Wicked fans can get another trip down the yellow brick road with Canadian Stage’s winter panto, The Wizard of Oz: The Toto-ly Awesome Family Musical. This rendition of the classic tale is taking audiences of all ages down to ‘TorOZto,’ for a hilarious romp. With astonishing sets, spectacular costumes, and the promise of very silly parodies of hit songs by Beyoncé, Billie Eilish and more, this is a highlight of the holiday season. More Info

When: December 6-January 5, 2025

Where: The Elgin and Winter Garden Theatre Centre

 

 

 
 
 
 
 
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Game Night

All About Intimacy is hosting their very first games night! With a focus on community-building, make new friends through games, laughter, and fun conversations while playing fun games like We’re Not Really Strangers and Askhole. This is a 2SLGBTQ+ friendly event and visitors are encouraged to explore what it’s like to talk about parts of our lives that we don’t always talk about. More Info

When: December 10

Where: The Theatre Centre

 

 

 
 
 
 
 
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Gay AF Christmas Spectacular

The 5th annual Queer Christmas tradition described as  “funny, heartwarming” returns to Toronto 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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Comedy Shorts Festival

WILDsound is coming to Toronto to showcase the best comedy short films from the last year from around the world. The lineup includes films from Canada, USA, the UK and Sweden. This is a free/PWYC event and will be followed by a Q&A with filmmakers in attendance. More Info

When: December 12

Where: Carlton Cinemas

 

 

 
 
 
 
 
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Les Femmes Fatales Presents Beautiful Neko

Les Femmes Fatales are back for another holiday-inspired cabaret show. Beautiful Neko explores themes of femininity, sexuality and sensuality, power, deviancy and resistance, and she is joined by several other showgirls including Ravyn Wngz, Petra Queen Of the Nile and Belle Jumelles. More Info

When: December 13

Where: Buddies in Bad Times Theatre

 

 

 
 
 
 
 
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Seeking Mavis Beacon

Hot Docs is hosting a free screening of Seeking Mavis Beacon as part of their For Viola series, a screening series centering BIPOC-led stories and filmmakers, named in honour of Canadian civil rights icon Viola Desmond. The film follows a pair of self-proclaimed “e-girl detectives” as they probe the disappearance of cultural icon, Mavis Bacon, frontwoman for one of the best-selling software products of the early digital era: Mavis Beacon Teaches Typing. More Info

When: December 13

Where: Hot Docs Cinema

 

 

 
 
 
 
 
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An Evening of Haunted Holiday Stories

For those who aren’t quite ready to give up spooky season, Fox Theatre is hosting An Evening of Haunted Holiday Stories. The night will include tales from Storytellers of The Haunted Walk of Toronto, as well as a screening of a themed classic short film.  More Info

When: December 14

Where: Fox Theatre

 

 

 
 
 
 
 
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The Flame Within

Described as a transformative evening of creativity and reflection, The Flame Within is an Etre Art Club event for reflecting on the year and fostering inspiration for 2025. Attendees can look forward to candle decorating, enjoying mulled wine, seasonal refreshments, and holiday music to elevate their evening.  More Info

When: December 14

Where: Centre for Social Innovation – Spadina

 

 

 
 
 
 
 
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The Winter Market

There are two more opportunities to visit The Winter Market at Evergreen Brick Works this season. Ontario Artisan Market and Ontario Vintage Market are joining again this year to bring vintage clothing, handmade art and more from 60+ vendors to Toronto. The event will also have ​​a food court and food trucks selling delicious food and drinks so you can stay energized to shop.  More Info

When: December 15 & 22

Where: Evergreen Brick Works

 

 

 
 
 
 
 
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Cocktails & Candy Canes

For a chic holiday celebration, look no further than Cocktails and Candy Canes, an evening of holiday songs from old classics to new favourites, jazz to gospel – and everything in between. Featuring professional musical theatre artists including Cara Adams, Lana Carillo, Gabi Epstein and more, Toronto Musical Concerts is excited to bring another high-quality musical concert to the city. More Info

When: December 16

Where: Hugh’s Room Live