It's The Most Wonderful Time Of The Year (Really) At Toronto's Holiday Attractions

The festive season. The holiday season. The winter holidays. Whatever language you use, the period of time between late November and early January is a peak season for joy. Whether you celebrate a particular tradition or you just get sentimental when you see people ice skating to classical music in Nathan Phillips Square doesn't matter. This is a time of year when we can all stop being cynical. As Linus Van Pelt of Charlie Brown taught us years ago, we don't need to be led by the commercial side of the holidays.

An evergreen is eagerly anticipated in Nathan Phillips Square every year. Once it is hoisted, the festivities unofficially begin. As we have well seen, it is not just December, but November that becomes drenched in holiday spirit, hoping to spark the holiday warm-and-fuzzies. Other people want the Starbucks red cups and Holt Renfrew Christmas windows to start at a later time, say, closer to the actual holidays that they are marking.

Whenever you are ready for it, the attractions that are designed to get your nostalgia pumping are ready and waiting. Whether you go to the Distillery's beloved Christmas Market in all its cobblestone glory or find the ugliest Christmas sweater at the Seasons Christmas Show, the festive season in Toronto is something special. 


Black Creek Pioneer Village is available year-round to remind us that there was a time when Smartphones didn't rule the world. Christmas by lamplight is set for December 9, 16 and 23 from 6pm-9:30pm. The glow of lamplight will set a festive tone to see the village while enjoying music, 19th century treats (including gingerbread) and special activities. The 35 restored buildings from the 1860s are dressed up in their festive glory, and carollers come by in traditional attire to get you feeling warm and holiday fuzzy. Lamps, lanterns, fireplaces and candles cast a beautiful glow over the village while you enjoy those chestnuts roasted over an open fire.

Recommended for Things to Do in December because: Christmas has been special even before it was commercial and Black Creek reminds us of this.

Courtney's expert tip: For a full night, enjoy a traditional Christmas dinner in the Canada West Room at 5:30 or 8:30pm. Reservations strongly recommended.

Read more about Black Creek Pioneer Village →

DJ Skate Night
Photo courtesy of Brian Medina

What better way to celebrate winter than in the open air with hundreds of your closest (Facebook) friends? Toronto's top DJs spin tunes for free Saturday nights at Harbourfront's Natrel Rink (from December 16-February 17 in 2017). Set against the beautiful backdrop of Lake Ontario, it offers the romance of winter with a heated indoor locker room for those times when you can't feel your face. There is always a special holiday party edition in December with festive music and hot chocolate. The rink is frequently open during the week for skating lessons if you need to brush up on your skills. Get ready to be seriously cool.

Recommended for Things to Do in December because: Tis the season for a little outdoor skating fun. It is perfectly timed before you go into hibernation.

Courtney's expert tip: Food and drinks are available for purchase at the rink-side restaurant, Lakeside Local Bar & Grill.

Read more about DJ Skate Night →


Toronto is not exactly the first place you go when you get the craving for a castle. However, in the middle of an upscale neighbourhood right near downtown Toronto, there is a majestic castle which was built in 1911 by a Canadian industrialist. Casa Loma has been open to the public for years and offers tours of the castle's 98 rooms, 1,800-bottle wine cellar and 800-foot underground passage leading to the home's stables. During the festive season, there is the chance to listen to Christmas carollers, indulge in gingerbread, ice cookies and tell Santa if you really have been good this year. There is also a 25-foot tree that greets visitors in the Great Hall, making for fantastic holiday card (or let's be honest, Instagram) photos.

Recommended for Things to Do in December because: Over 100 years of Christmas experience and Casa Loma is still going strong.

Courtney's expert tip: Every December, there is a Christmas ball at Casa Loma that includes a live holiday concert with Toronto's Symphony Orchestra.

Read more about Casa Loma →


When you first find your way in between Spadina and Bathurst and then in between College and Dundas in Toronto, you may feel that you haven't found anything special at first. However, as you start your walking journey throughout Kensington Market, you quickly realize you have entered the realm of something unique. Kensington has quite a history, but today it stands as a multicultural community of noncomformists. Many Victorian homes retain their original architecture but have been transformed into shops that range from excellent cheesemongers to local designers. During the holidays, it becomes the ideal place for one-of-a-kind gifts. In addition, there is a Christmas Food Tour where you can enjoy an array of treats, from artisanal cheeses to mulled wine.

Recommended for Things to Do in December because: From a solstice parade to a Christmas Food Tour, Kensington wants to make sure that you have a very funky holiday season.

Courtney's expert tip: Visit on December 21 for the Kensington Market Winter Solstice Parade which has Hanukkah candles, the fire of Christian faith and the pagan celebration of the solstice.

Read more about Kensington Market →

The National Ballet of Canada has performed for over 50 years and over 10 million people in the heart of Toronto. The company performs works from both contemporary and classical masters and employs some of Canada's top-notch artists, dancers and musicians. It shares the Four Seasons Centre with the performing arts with the Canadian Opera Company, a venue that is aesthetically and acoustically all class. And every holiday season it breaks out the Nutcracker, a beloved holiday tale that they perform flawlessly with 187 costumes in each performance. It is a spectacle that will make you believe in holiday magic (or at least the Sugar Plum fairy).

Recommended for Things to Do in December because: An opulent ballet with a layered tale of a sparkling winter realm. The Nutcracker is a perfect December treat.

Courtney's expert tip: Buy your tickets early to save big and do consider going to one of the January performances for the best rates.

Read more about The National Ballet of Canada →

Cavalcade of Lights
Photo courtesy of City of Toronto

Created in 1967 to showcase Toronto's newly constructed city hall and the Nathan Phillips Square public space that fronts the building, the Cavalcade of Lights today kicks off a month of holiday festivities with a tree lighting ceremony in the square on the last weekend of November. The buildings surrounding Nathan Phillips Square are decorated with festive LED lights, making the display even more cheerful. The opening event is marked by free musical performances including the Les Chausseurs de RĂªves and the Lemon Bucket Okestra. Cap it off with fireworks with a countdown (who needs to wait for New Year's Eve?). A DJ skating party keeps the festive vibe going all the way to 10:30pm, when your cold fingers may need a break anyway.

Recommended for Things to Do in December because: The good side of the holidays is seeing lights ignite the hearts of the Scroogiest of people.

Courtney's expert tip: The official City of Toronto Christmas tree this year is more than 60 feet high. If you can't get close (this is a very busy event!), at least you will get a good shot.

Read more about Cavalcade of Lights →

No matter what Charlie Brown seems to tell us every holiday season, we can't seem to get it out of our collective skulls that Christmas is, at least a little bit, commercial. We like the shiny wrapping paper. We rejoice over ugly Christmas sweaters. We get reindeer cookie cutters to make the perfect holiday pancakes for our less than perfect holiday families.The Seasons Christmas show runs for three days every November (17-19 in 2017) and it celebrates the part of you that still refuses to believe that there isn't magic behind finding the ideal present. Cue Michael Buble's Christmas album, wrap a scarf around your neck and get prepared to "fa la la" all the way to the cash register.

Recommended for Things to Do in December because: 300 exhibitors have what you need to entertain, gift and decorate for the whole holiday season.

Courtney's expert tip: Friday night has 2 for 1 admission after 5pm, if you are used to moving fast and deciding quickly.

Read more about Seasons Christmas Show →

Santa Claus Parade
Photo courtesy of Santa Claus Parade

This 115-year-old tradition (the "original" Santa Claus Parade) still has parents bundling up their kids and loading up mugs of hot chocolate. Most Torontonians have memories of waiting anxiously for Santa Claus to come to town at this non-for-profit parade. Santa made his first appearance in 1905! The historical charm has been preserved, as some of the floats from nursery rhyme characters date back from the early 1900s while others are more modern, such as the Harry Potter animated float or the one dedicated to Hockey Night in Canada. In 2019, the parade is celebrating their General Manager and Creative Director, Alf Iannarelli, who has been a part of 50 parades himself. Over 2,000 costumed volunteers help to spread the holiday joy, while over 20 marching bands play carols and classic tunes. It is a big deal to get chosen to participate in the parade. By the time Santa Comes around with his signature "ho ho ho" the crowd has no chance but to be enchanted.

Recommended for Things to Do in December because: Trends come and go, but Santa Claus never goes out of style.

Courtney's expert tip: Important note for 2019: the parade has changed its route! It is now starting in the east end making its way into the centre. See the website for the parade map.

Read more about Santa Claus Parade →

Holiday Fair In The Square
Photo courtesy of Holiday Fair In The Square

When it's beginning to look a lot like Christmas, and you are Canadian, you strap on a pair of ice skates and hope for the best. The top place to do this during the holiday season is undeniably Nathan Phillips Square in Toronto. Located right in front of City Hall and around the corner from the Eaton's Centre and popular restaurants, it is a great activity to sandwich between other downtown pursuits. Bring your own skates for free exercise or rent skates for $10 or less. During the holidays, the rink sparkles with lights and displays a large holiday tree for Toronto's version of New York's Rockefeller Centre. The Holiday Fair's dates for 2019 are December 7-23. Expect an elegant Christmas market, a Holly Jolly Midway and Polar Point Bar to shiver away in with your nearest and dearest.

Recommended for Things to Do in December because: An artisan village, an ice rink and fire pits. Can you get more festive than that?

Courtney's expert tip: This is a Christmas hot spot, so of course, Santa has been invited. He is there on weekends between 12pm and 8pm for photos.

Read more about Holiday Fair In The Square →

Toronto Christmas Market
Photo courtesy of Arjun Yadav

If you can't remember the last time you felt the Christmas spirit, then put your bells on and get thee to the Toronto Christmas Market. From life sized gingerbread houses for children to a variety of beer and mulled wine gardens, you will feel warm and cozy in your heart even if the rest of your extremities are a tad chilly. It is ranked as one of the top ten Christmas markets in the world. Stand by roaring fire pits, marvel at the sparkling lights and tap your toes to nostalgic music sung by the Candy Cane Carollers. Now there will be no pressure on your family - you will have already had a very merry Christmas.

Recommended for Things to Do in December because: A one month street festival dedicated to the tradition and romance of Christmas.

Courtney's expert tip: Not surprisingly, Santa is there. Santa's hours typically go from 2pm, but do check their website for his exact whereabouts. He is a busy man.

Read more about Toronto Christmas Market →


Meet Courtney Sunday

Courtney Sunday has lived in England, Switzerland, Canada and the US, finding her way into the professions of freelance writing and yoga teaching in between travel opportunities. She learned...  More About Courtney