32 festive and holiday-themed things to do in Toronto this December

Dec 2 2021, 3:57 pm

It’s finally the month of December which means it’s acceptable to play Mariah Carey’s “All I Want For Christmas” on repeat while you scour the internet to find all the holiday-themed events happening in Toronto.

But don’t worry, we’ve got you covered. From holiday-themed bars to festivals, dance parties, and more, there are a lot of things to do in Toronto this month.

Here are just a few of the many events available for everyone and anyone to enjoy this holiday season in Toronto:

Skate on this rooftop patio rink

Sky Skate is back this year at The Porch rooftop patio in Toronto with an improved experience. Something about skating under the moonlight and enjoying the breathtaking view of the CN Tower sounds magical. This one-of-a-kind experience will provide family fun events during the day, rooftop date nights, and parties at night.

When: Monday to Thursday from 3 pm to 10 pm, Friday from 3 pm to 12 am, Saturday from 12 pm to 12 am, and Sunday from 12 pm to 10 pm
Where: The Porch rooftop – 250 Adelaide Street West

Explore this life-sized Candyland

A life-sized Candyland installation with a massive gingerbread house has been unveiled at Toronto’s Dufferin Mall for the holiday season. Until January 3, shoppers will be able to explore the magical Candyland installation and take pictures in a life-sized snow globe and candy cane selfie stations.

When: Until January 3
Where: Dufferin Mall – 900 Dufferin Street

Get into the holiday spirit at Canada’s Wonderland Winterfest

Canada’s Wonderland has brought back its holiday-themed WinterFest this year. The immersive holiday experience features millions of lights, many Christmas trees throughout the park, more than a dozen live shows, and ice skating on Snow Flake Lake.

When: Select nights between November 13 to December 31
Where: Canada’s Wonderland — 1 Canada’s Wonderland Drive, Vaughan

Check out Holiday Fair in the Square and Nights of Lights

Holiday Fair in the Square is back for the season in a new location, and it’s bigger and brighter than ever, thanks to a new partnership with Nights of Lights. The massive winter wonderland, in support of Epilepsy Toronto, is now open and runs until January 2. Both the Holiday Fair in the Square and Nights of Lights are located at Assembly Park in Vaughan. The fair moved from its original home in Nathan Phillips Square to accommodate the new features and attractions.

When: Until January 2, 2022 (closed on Mondays, Tuesdays and December 25, open on December 27 and 28), From 5 pm to 11 pm (Wednesdays to Fridays), 12 to 11 pm (Saturdays and Sundays)
Where: Assembly Park – 80 Interchange Way, Vaughan

Watch a throwback holiday movie 

Catch Home Alone at the Throwback Cinema this month. The nostalgic movie is sure to get you in the holiday spirit. Tickets are on sale.

When: December 11 at 4 pm
Where: Revue Cinema – 400 Roncesvalles Avenue

Picasso exhibit

The AGO is presenting Picasso: Painting the Blue Period. It is the first exhibition in Canada that focuses on the early works of the modernist artist. It will feature more than 100 objects from 15 different countries. There will be paintings, sculptures, and works on paper by Picasso, including works by artists the Spaniard is known to have studied before and during the Blue Period.

This exhibition is curated by AGO’s Kenneth Brummel and Dr. Susan Behrends Frank and co-organized by the AGO, The Phillips Collection from Washington, DC, and support of the MusĂ©e national Picasso-Paris.

When: Until January 16, 2022
Where: 317 Dundas Street West

Eat at the Holiday Street Market

Street Eats Market is back this holiday season with a massive, 40,000-square-foot holiday market with food, rides, and Christmas spirit to Scarborough this weekend. The Holiday Street Market is returning to the Scarborough Town Centre on December 3 for three festive weeks. Run by the popular Street Eats Market, the holiday event will feature a marshmallow fire pit lounge, sweet and savoury food trucks, a hot cocoa bar, and a maple syrup sugar shack.

When: December 3 to 24
Where: Scarborough Town Centre, 300 Borough Drive, Scarborough

Enjoy a Dino Holiday

Have you ever been faced with the difficult decision of choosing between seeing dinosaurs and seeing Santa? Well, a Markham festival found a solution for that. Dino Holiday is a huge indoor event full of massive dinosaurs completely decked out for the holidays. There are more than 45 animatronic dinosaurs to fulfill every Jurassic Park (or Jurassic World) fan’s dreams. There are games and carnival rides, too! As if that wasn’t enough, it’s all indoors, so you don’t have to worry about getting cold as winter weather approaches.

When: December 17 to January 2, including Christmas Day.
Where: Markham Fairground, 10801 McCowan Road, Markham.

Take your pup to the Howliday Market

An indoor howl-iday market for pups and their owners is coming to Toronto with over 30 local businesses to shop from. Toronto’s Howliday Market will kick off on December 11 from 12 pm to 8 pm at Daniels Spectrum, 585 Dundas Street East. The event will welcome over 1,000 people and their four-legged friends for a fun-filled day of shopping for gifts like Holiday bandanas for dogs, chef-inspired treats, “Dog Mom” sweaters, and more.

When: December 11 from 12 pm to 8 pm
Where: Daniels Spectrum at 585 Dundas Street East

PetSmart Photos With Santa

It wouldn’t be the holidays without some cute Santa photos with our four-legged friends, now would it? The best part? It’s absolutely FREE. Starting this weekend at PetSmarts across Canada, you can book your pet in for a special one-on-one photo with ole Saint Nick himself. If you haven’t found the perfect holiday outfit for you or your pet and can’t make it this weekend, you are in luck. You can book for December 11, 12, 18 and 19 as well.

When: December 4, 5, 11, 12, 18 and 19
Time: 12 to 3 pm

Dandylion’s Holiday Dog Festival

A Holiday Dog Festival is coming to Toronto, and it’s full of fun activities and holiday treats to enjoy with your pup. Dog care company Dandylion will be hosting a charity holiday dog festival in Toronto at 25 Liberty Street on December 5. The day is full of festive activities for dogs and their owners to enjoy, like custom ornaments, holiday family portraits, puppuccinos, barkcuterie boards, and more.

When: December 5 from 12 pm to 5 pm
Where: 25 Liberty St, Unit 200

Check out Eataly Toronto’s Holiday Market

Toronto’s Eataly has become the newest exclusive festive spot, showcasing its Italian treats and gifts throughout its store and special holiday market. Guests can now enjoy the ultimate Italian holiday experience with culinary gifts, themed gift baskets, and more until January 2.

When: Until January 1, 2022

Go for a skate at The Bentway Trail

The Bentway Skate Trail is opening back up in Toronto this season and will be welcoming the public for special events and lessons later this month. Sharpen those skates and get ready to hit the ice because the Bentway Skate Trail will open for the skating season on December 18.

When: Starting December 18, 12 pm to 9 pm every day
Where: The Bentway 0 250 Fort York Boulevard

Enjoy the Christmas spirit at Miracle Toronto Pop-up

Miracle Toronto is back this year, bringing the excitement of Christmas to its annual pop-up event. Since its humble beginnings in 2018, Miracle has popped up at different locations across the city. Nothing screams Christmas like kitschy holiday décor and a ton of festive cocktails.

When: November 25 to December 26 from 5 pm to 2 am every day
Where: Miracle on Bloor Street – 875 Bloor Street West

Explore a different side of Christmas at Sippin’ Santa Pop-up

Christmas Day is just a month away, and one of the best ways to get into the holiday spirit is with a festive cocktail in hand. The Sippin’ Santa holiday pop-up bar officially opened its doors, welcoming guests to its Tiki-inspired holiday bar. You’ll feel like you’re in a tropical paradise, escaping the winter blues and celebrating the holidays in the best way possible.

When: November 25 to December 26 from 5 pm to 2 am every day
Where: Sippin’ Santa – 866 Bloor Street West

The Cozy Christmas indoor pop-up

This Christmas market is coming to Toronto next week, and it’s filled with holiday-themed drinks, delicious food, fun activities and over 40 vendors. The Cozy Christmas indoor pop-up will kick off on December 14 and run until December 19 at 300 King Street East. They have a ton of boozy drinks on their lineup like “Naughty n’ Ice,” “The Grinch,” “Santagria,” “Rudolph’s Regret,” and “Jingle Juice.”

When: December 14 to 19 from 12 pm to 11 pm
Where: 300 King Street East

Eat and drink at Papi Chulo’s Mistletoes & Margaritas

It’s all about the Christmas joy at Toronto’s Papi Chulo’s! The spot known for its margarita towers has transformed its space into the ultimate festive pop-up. They’ve decorated the interior indoor space from head to toe in holiday cheer, welcoming the season with open arms.

When: Until January 2
Where: 121 Ossington Avenue – Papi Chulo’s

Support women-owned businesses at this holiday market 

This new holiday market in Mississauga features vendors from more than 35 women-owned businesses. The co-founders of the Run The World Summit brought their Run The World Holiday Market to Square One and will run until December 24.

When: Until December 24
Where: Square One Shopping Centre

The Immersive Nutcracker, A Winter Miracle

Toronto is has a new immersive experience, but this time it’s festive. The city is hosting the world premiere of The Immersive Nutcracker, A Winter Miracle. Guests are placed in the middle of the classic Nutcracker story as dazzling projections swirl around the room and dancers from the Bolshoi Theatre twirl to the music of Tchaikovsky.

When: Until December 24
Where: 1 Yonge Street

Explore Toronto’s largest outdoor holiday fest

Toronto’s biggest outdoor holiday festival is put on by Concierge Club and features 16 festive holiday zones and a huge photo-op station for pictures with Santa. The event runs until December 26. Its open Wednesday to Sunday from 5 pm to 11 pm.

When: Runs until December 26
Where: Bandshell Park in Exhibition Place

Explore this year’s One Of A Kind Winter Show

The One Of A Kind Winter Show is back in the city this year with over 400 artisan vendors to discover. The event is located at the Exhibition Place’s Enercare Centre and vendors from across the country are set to showcase their works of art from home dĂ©cor to fashion, jewellery, artisanal food items, toys and more.

When: November 25 to December 5 – Monday to Saturday from 10 am to 9 pm.
Where: Enercare Centre – Exhibition Place, 100 Princes Boulevard

Drink the night away at Miracle Toronto and Sippin’ Santa

Miracle Toronto and Sippin’ Santa holiday pop-up bar officially opened their doors on November 25 and are now serving the most delicious cocktails, perfect for the season.

When: November 25 to December 26 from 5 pm to 2 am every day
Where: Miracle on Bloor Street – 875 Bloor Street West, Sippin’ Santa – 866 Bloor Street West

Sip on the booziest drinks at The Thirsty Elf pop-up

The Thirsty Elf is back with creative holiday cocktails, Christmas sweaters, kitschy decor, and all your favourite holiday songs. This year’s festive cocktail menu is curated by Fairmont Hotels’ Director of Beverage, Rus Yessenov.

When: November 19 until December 18, Thursday to Saturday from 4 pm to 11 pm
Where: Avenues Level of Fairmont Royal York

Dance the night away at this Bollywood Party

Grab your friends and check out Bollywood Buzz, playing only Bollywood beats, Top 40, EDM, and mainstream Bhangra music. Tickets are available online now.

When: December 17
Where: The Axis Club Theatre at 722 College Street

Explore the Distillery Winter Village this holiday season

The Christmas season has arrived in Toronto as The Distillery Winter Village officially opens. The renamed and rebranded Toronto Christmas Market opened at 6 pm on November 18, lighting its 55-foot-tall Christmas tree. Visitors can stroll the cobblestone streets beneath starlit canopies, gaze upon the dazzling tree, indulge in delicious food, and check off every gift on their holiday shopping list.

When: November 18 to December 31, and on select days through December
Where: 55 Mill Street

Get tickets for Sweaters n’ Snowflakes

The Sweaters n’ Snowflakes pop-up is here this winter for the ultimate holiday experience. Guests will jump into a winter wonderland and experience the fun and joy of the holidays. When it comes to food and drink options, it seems almost endless. There’s a cocktail and wine bar where guests can order holiday-inspired cocktails and mulled wine. For larger groups, they also have wine tastings available.

When: December 3 to 26 and 31
Where: 621 Richmond Street

Check out stackt market’s Holiday Hills

Toronto’s stackt market is hosting its massive, six-week holiday festival, Holiday Hills until December 31, and it’s full of shopping, live music, and more. It will feature live music showcases, art, holiday-themed workshops, and DIYS, a drag brunch, and weekends of vendor markets in time for Christmas shopping.

When: November 23 to December 31
Where: stackt market – 28 Bathurst Street

Drink at Project Gigglewater holiday bar

Christmas has started early at Project Gigglewater as the Toronto bar transforms into the ultimate holiday pop-up with boozy cocktails and treats. Project Gigglewater has covered its space from top to bottom in all things Christmas, encouraging guests to enjoy the holiday season with a drink in hand. Along with their holiday theme, they have designed a new menu filled with themed drinks and food.

When: Now until December 26
Where: Project Gigglewater – 1369 Dundas Street West

Warm-up with some hot chocolate from Lindor

Lindt Canada is hitting the road and will be spreading holiday cheer across Toronto with its LINDOR hot chocolate truck. Each visitor will be given a delicious hot chocolate, and festive treats while supplies last.

When: December 1 to 3
Where: December 1 – Queen Street West at 12:30 pm, Bloor & Yonge at 3:30 pm, December 2 – Union Station at 10:30 am, University & College at 3:30 pm and December 3 – Queen & Bay at 10:30 am, Trinity Bellwoods at 2 pm and Roy Thompson Hall at 5 pm

Mix and mingle at The Rec Room

Make some new friends and wonderful memories at this holiday-themed event. It will be a night full of trivia fun and unlimited play at The Rec Room. Each table will have board games, food and drinks too! The ticket cost covers the entrance fee, unlimited gameplay for 2 hours, and the event organization.

When: December 19 from 5:45 pm to 10 pm
Where: The Rec Room Toronto 255 Bremner Blvd

Enjoy a Sunday brunch with Erin Brokobić

Join drag star Erin Brockobić for a fun-filled Sunday brunch, all-you-can-eat, of course. There are select dates and times, whichever works for you. The ticket cost includes the all-you-can-eat brunch and the show.

When: December 5, 12 and 19
Where: Glad Day Bookshop at 499 Church Street

Free outdoor skating rink at Union Station

Get ready to strap on a pair of skates and head over to Front Street — Toronto’s beloved outdoor skating rink has returned to Union Station this holiday season, and it’s totally free. In collaboration with Union Holiday and TD, the skating rink opened to the public on November 29 and will remain open every day until January 2, depending on the weather.

When: Until January 2
Where: Union Station — 65 Front Street West Toronto, ON

Karen DoradeaKaren Doradea

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