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To Do: December in Toronto


to do: december in toronto

It’s officially December! Which means that Torontonians are bustling to get in on all the holiday events popping up over the GTA.

We at Heel Boy can’t wait to join the fun. Continue reading to get filled in on all the happenings Toronto has planned for December!

December GTA

Home Alone in Concert

The Toronto Symphony Orchestra presents Home Alone in Concert with the orchestra and Resonance Youth Choir singing along with the film. Enjoy this Christmas classic to the max at Roy Thomson Hall on December 6th and 7th.

Union Station Holiday Market

The Union Station Holiday Market returns to Toronto better than ever thanks to a newly renovated space inside the massive transit hub. This is always one of the city’s busiest holiday pop-ups. Now in its third year, the market arrives for 12 days between December 5th to 16th. Twenty local businesses, designers, artisans and gourmet food vendors will sell goods out of their custom booths at this vibrant little market every day! 

Kensington Market Winter Solstice

Layer up and celebrate the longest night of the year in Kensington Market with the annual Winter Solstice Parade. Presented by Red Pepper Spectacle Arts, the parade departs at 7 p.m. at the corner of Oxford and Augusta. The event is free, but if you’d like to buy a lantern to carry as you walk with the parade you can do that on the steps of St. Stephen’s Community House from 5 to 6:30 p.m.

Toronto Christmas Market 

Inspired by the German Christkindlmarkt, this hyper-festive event celebrates the sounds, sights and scents of Christmas. Set in the cobblestone-lined Historic Distillery District, the market brings together local craftspeople, artisanal food-makers and spectacular light displays for a truly merry experience. Free admission Tuesday to Friday and $12.00 admission Friday evening, Saturday and Sunday. The market goes until the 22nd of December.

DJ Skate Night at Harbourfront

Bundle up! This popular event at Natrel Rink sees local and international DJs spinning tunes you can skate to on Saturday nights. From December 14th to February 15th you can shimmy your way through the winter season.

December to do

Holiday Fair in the Square

In the heart of Toronto at Nathan Phillips Square, the Holiday Fair in the Square runs December 7th – 23rd. Combining the charm and elegance of a Christmas market with the excitement and allure of a thriving winter carnival, Fair in the Square is a new favourite Toronto holiday tradition. Whether you’re shopping for that unique, perfect gift, taking the family out for an afternoon of skating, rides and games, stopping by for a quick lunch and some seasonal treats, or enjoying an evening drink at the heated Polar Point Bar, Holiday Fair in the Square has festive fun for everyone! Across the way you can View the holiday windows at Hudson's Bay and Saks Fifth Avenue! The animated windows promise to make your jaw drop. The windows will be on display through to January 3rd. 

Free Holiday Flicks at Hot Docs Ted Rogers Cinema

Get ready, you can catch a few beloved Christmas classics for free at Hot Docs Ted Rogers Cinema on Bloor Street. at various points between December 14th and 21st. you can head over to see It’s a Wonderful Life, A Very Harold and Kumar Christmas, White Christmas, National Lampoons Christmas Vacation, A Christmas Story and The Holiday at various times during the week. Free tickets are offered on a two per-person, per-film basis and it’s encouraged to bring a food bank donation in support of The Stop. The Cinesphere at Ontario Place will also be putting on showings of a few Christmas classics throughout December!

Christmas at Casa Loma

For a truly unique and memorable Christmas experience, a visit to Toronto’s castle is a must. This year’s theme is a nutcracker Christmas. The castle’s spectacles of illusions and wonder will amaze audiences young and old alike. Guests will be surrounded by holiday magic throughout the castle which will be resplendent with holiday décor, including a 40ft tall tree in the Great Hall and eight other signature trees by talented Canadian designers.  Guests can also explore the holiday magic of Casa Loma…at night from December 15th to 30th. Wander through the dazzling lighting display in the gardens and experience all of Casa Loma’s holiday festivities as well as our outdoor holiday Christmas Market and performances by the Casa Loma Holiday Orchestra. Open daily until January 5th.

December toronto

The Ward Cabaret

The Ward Cabaret reimagines the vibrant sounds of Toronto's first cross-cultural community. When they came to Toronto they brought their cherished cultural treasures: deep traditions of stories, music and song. From December 12th to 22nd, The Ward Cabaret, created with the collaboration of award-winning artists, shares the key to the sound, “vibration” and meaning of a time and place that holds the secret of what Toronto has become: the most diverse city on the planet.

Winter Village at Evergreen Brick Works 

Celebrate the holidays in a reimagined historic brick factory. Skate on the picturesque outdoor skating rink, shop local craft goods at the Holiday Market, listen to live music and end your stay with tasty and toasty eats and drinks. Evergreen’s Winter Village is free to attend, open every weekend from November 30th to December 22nd!


Up until December 31st, Canada’s Wonderland will be magically transformed into a winter Wonderland full of enchantment and holiday cheer during WinterFest! Become immersed in the season’s spirit with spectacular holiday lights and décor, world-class live entertainment, savoury treats and fanciful Christmas activities.

Aurora Winter Festival 

The CNE is presenting this year’s Aurora Winter Festival. Toronto’s Ontario Place will be transformed into a magical winter wonderland with a beautiful skating rink, a tube park, massive light displays, a Christmas Market, amusement rides, food gardens, magical characters, and plenty of other exciting activities. Experience Canada’s largest winter festival this holiday season. The festival runs until the 5th of January, don’t miss out!

What to do in toronto

Conservatory by Candlelight

It’s December! Which means Allan Garden’s conservatory is decorated and filled with thousands of flowering plants, over 30 varieties of poinsettia and amazing seasonal topiary masterpieces made entirely of plant material. Breathtaking floral scenes with thousands of colourful blooms, vines and lush plants from around the world transform our conservatories into memorable, must-see winter destinations. Join the conservatory for a Pomander Making Party on Saturday, December 14th, and drop by the Children’s Conservatory to celebrate the solstice with the Friends of Allan Gardens. Make a pine cone bird feeder to take home, pick up a plant at their small pop-up sale and have a cup of hot cider. No registration is required. Runs until the 12th of January.

The National Ballet of Canada

Every holiday season The National Ballet of Canada breaks out the Nutcracker, a beloved holiday tale that they perform flawlessly with 187 costumes in each performance. Treat yourself to an opulent event with a layered tale of a sparkling winter realm. The Nutcracker is a perfect December treat, running this year from December 12th to January 4th.

So much to do in such little time! We can’t wait to hit all these spots this holiday season!

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