The season of twinkling lights and festive cheer is upon us! Whether you want to take in an eye-popping winter wonderland, a grand display of lights, or a holiday-themed comedy or stage show, there is an event for you in Toronto this holiday season.

Christmas at Casa Loma

The spectacle of the holiday season at Casa Loma is always a sight to behold. Take a stroll through the castle grounds to experience the magic of the grand light displays, or see the breathtaking interior decor, including a 40 ft tall tree and eight other signature trees created by talented Canadian designers.

When: December 1-January 6

Where: Casa Loma

Chris, Mrs. – A New Holiday Musical

This heartwarming story follows the Chris family, who always manages to add a little magic to the everyday. This new musical stars 17 talented Canadian actors ready to deliver a performance full of mischief, mistletoe, and holiday cheer, perfect for the whole family.

When: December 5-31

Where: The Winter Garden Theatre

A Christmas Carol 

This immersive production of the classic Christmas story invites audiences into the historic Campbell House Museum to follow Ebenezer Scrooge’s journey to redemption. Brought to life with original scenes, characters, songs, and dialogue, the production has received rave reviews in past holiday seasons, and will bring plenty of merriment in its fifth year. 

When: December 6-22

Where: The Campbell House Museum

Toronto Symphony Orchestra Holiday Concerts

Experience a magical symphony of sounds at a Toronto Symphony Orchestra holiday concert. Whether it’s the energetic score of Home Alone, a selection of holiday favourites featuring legendary Canadian jazz vocalist Molly Johnson, or a traditional performance of Handel’s Messiah, there’s sure to be a TSO concert this season to lift your spirits.  

When: December 7-23

Where: Roy Thomson Hall

The Cans Film Festival

Enjoy a holiday film festival for a good cause! The Cans Film Festival invites moviegoers to bring donations of canned goods or non-perishable food items to any Imagine Cinemas location, in support of 9 food banks across Ontario. Anyone who donates can enjoy a free screening of either Polar Express or National Lampoon’s Christmas Vacation.

When: December 9 and 10

Where: All Imagine Cinemas locations

Photo by Dahlia Katz

101 Holiday Movie Moments

This holiday comedy spectacle will take audiences on a journey through a heartfelt and hilarious reimagination of the traditional Hallmark Christmas movie plot, blending nostalgia, laughter, sing-a-long moments, and 101 movie references you’ll love, with a star-studded cast, including Ann Pornel and Kirsten Rasmussen. 

When: December 12-31

Where: Comedy Bar Danforth

Holiday! An Improvised Musical

Inspired by Stephen Sondheim’s Company, this improv comedy musical incorporates suggestions from the audience to weave together a series of vignettes and songs exploring the true meaning of the season. 

When: December 13-17

Where: The Assembly Theatre

MILF & Cookies

In this lively holiday comedy show, loveable comedian Anne Marie Scheffler leads her two best friends on a wild quest to visit Santa. Together, the MILF Squad uncovers juicy dating stories and ghosts of boyfriends past as they travel to meet the big man in red. Join Brampton on Stage for this hilarious celebration, perfect for a festive girl’s night out.

When: December 22

Where: Lester B. Pearson Theatre

Window Wonderland in the Junction

Window Wonderland is returning to the Junction, transforming the neighbourhood into a magical outdoor art gallery for the holiday season. Take in 20 spectacular augmented reality (AR) window installations and five murals at this immersive urban art experience. If you fall in love with a piece, purchase prints from the featured muralists at ARTiculations Art Supply. 

When: On now until January 31

Where: The Junction, between Dundas St West and Keele St

Winter Wonderland at Illuminarium at The Distillery District

Immerse yourself in a winter wonderland at The Illuminarium! Take in a dreamland full of festive sights with their state-of-the-art interactive technology, complete with a 360 degree immersive show, photo ops, a free hot coaco station. If you’re looking for a full day of holiday fun, combo tickets for The Distillery Winter Village are also available.

When: On now until January 7

Where: Illuminarium at The Distillery District, 28 Gristmill Lane

Cavalcade of Lights

Thousands of dazzling lights and festive art installations will illuminate Nathan Phillips Square as part of the city’s annual Cavalcade of Lights. Take part in free public skating, bask in the glow of the tree, and experience the buzz of festive cheer in the heart of the city.

When: On now until January 7

Where: Nathan Phillips Square

Holiday Markets

There’s nothing like the hustle and bustle of a holiday market at this time of year. The city is buzzing with plenty of pop-ups, indoor and outdoor markets with unique items made by local artisans. Check out our top 10 picks for delightfully festive shopping experiences.

Holiday Movies at Cineplex

See a holiday classic on the big screen this December at Cineplex. It’s A Wonderful Life, The Polar Express, The Grinch and more will be screening at Cineplex locations across the country.