12 Days of Toronto

As Toronto continues to shrug off its shell of scaffolding, Canada’s cultural capital has emerged, embracing its new, hip identity. But to truly experience this lakeside metropolis, you'll have to dive into its local haunts.

12 Days of Toronto with Starwood Hotels & Resorts

With over 140 languages spoken, Toronto is a multicultural smorgasbord of people, neighborhoods and attitudes. Just walk the streets and it feels like you’re traversing a global bazaar with every weekend bringing another cultural festival to celebrate.

Canadians don’t fear the cold, and the holiday season in Toronto is as vibrant as any other. Explore the Queen City this winter and get in the spirit with our top twelve to-do’s. Let the 12 Days of Toronto begin…

Cavalcade of Lights in Toronto Canada

Cavalcade of Lights

A Toronto tradition for over fifty years, the annual Cavalcade of Lights is the perfect way to kick off the holiday season. Taking place on Saturday, November 26 in Nathan Phillips Square, the event will feature the lighting of Toronto’s official Christmas tree, musical performances from some of Canada’s hottest artists, and a stunning fireworks display all in the heart of downtown Toronto. The tree is typically selected a year in advance and takes an astounding two weeks to decorate. Standing anywhere from 15 to 18 metres (55 to 65 feet), the illumination of this towering tree is a spectacle you won’t want to miss.

Toronto Christmas Market

Ranked as one of the Top 10 Holiday Markets in the world, the Toronto Christmas Market will be back in business from November 18 until December 22 at the Distillery Historic District. Open Tuesday – Sunday, this magnificent street festival features musical performances from a wide array of styles and genres, photos with Santa Claus for the kids, heated “hospitality lounges” where guests can enjoy a warm winter beverage, and plenty of unique vendors from around the globe. Whether you’re just stopping by for a quick Hot Toddie, or to pick up one-of-a-kind gifts for the whole family, the holiday cheer is contagious at the Toronto Christmas Market.

Skating at Nathan Phillip’s Square

Skating at Nathan Phillip’s Square

The Cavalcade of Lights is just the beginning of the winter fun in Nathan Phillip’s Square. Through mid-March, the Square hosts Toronto’s most famous outdoor ice rink. With the official Christmas tree and dazzling holiday lights in the background, Nathan Phillip’s Square becomes a postcard image for Christmas during the winter months. Skaters of all skill levels are welcome at this family-friendly rink, and skates are available to rent in both adult and children’s sizes. The rink will be open seven days a week this winter, including Christmas Day and New Year’s Eve. Happy Skating!


Nothing sounds better on a cold winter day than a hot, homemade meal. From January 27 to February 9, Winterlicious is back in Toronto, giving you the chance to experience some of the city’s best cuisine. Here’s how it works: Over 200 restaurants across Toronto offer unique three-course, fixed price lunch and dinner menus during what has to be the tastiest two weeks of the year. This culinary series also features spectacular cooking classes and demonstrations, dinner theatre, as well as tastings and pairings. For a comprehensive list of menus and participating restaurants, be sure to check the Winterlicious webpage. Bon Appetit!

Toronto Maple Leafs or Toronto Raptors game

Leafs or Raptors game

When the temperatures start getting colder, the Toronto sports scene starts to heat up. The cooler weather brings with it the return of basketball, and of course, hockey season. To see just how seriously Canadians take their sports, stop by the Air Canada Centre to watch the Raptors fight their way toward the NBA Championship, or the Maple Leafs compete for their 14th Stanley Cup victory. Snag your tickets for either team to get in on all the live sports action Toronto has to offer this winter.

Indoor sports

If you prefer playing sports to watching them, you’re in luck. Toronto offers a variety of indoor locations where you can stay active no matter what the weather outside looks like. Basecamp Climbing is an indoor rock climbing facility located just across from Christie subway station. The gym offers over 7,000 square feet of climbing space for novice and expert climbers alike, as well as rec classes just for kids. Or if you prefer a more casual sporting environment, the city’s multiple ping-pong lounges are great spots to escape the cold with friends for a bite to eat and a game of table tennis. Check out SPiN Toronto or Smash Ping Pong Lounge during your next visit.

Toronto Malls

You can’t have a holiday season without holiday shopping. In addition to specialty shops like the ones at the Toronto Christmas Market, you can find all the big name brands at one of the city’s world-class shopping centres. Recent expansions have brought new stores to both the Eaton and Yorkdale Centres just in time for holiday shopping. Seasonal decorations adorning the malls are pretty, but it’s the seasonal savings that really make a visit to one of these shopping centres worth the visit.

Santa Claus Parade in Toronto

Santa Claus Parade

Of Toronto’s many cherished Christmas traditions, one of the oldest and most anticipated has to be the annual Santa Claus Parade. Making its 112th running on November 20, the “Route of Ho-Ho Happiness” starts at Christie Pits and ends at the St. Lawrence Market. Torontonians and tourists alike line the streets to catch a glimpse of Kris Kringle, so make sure you arrive early to secure a spot. Or if you’d rather stay moving than stand still, the Holly Jolly Fun Run might be more your speed. Started in 2013, this festive 5k takes runners on the same route as the parade and is a great way to keep warm while being a part of the holiday fun.

Winter Cruise

A cruise on Lake Ontario may not sound like a typical winter activity, but Mariposa Cruises offers a variety of holiday cruise packages that will make you think twice. Hosting private events for parties from 50 to 300 people, Mariposa’s holiday cruises feature a buffet dinner, a professional DJ, and of course, unmatched views of the Toronto skyline. Mariposa also offers public dinner cruises year-round for those looking for a smaller-scale evening. A full list of public and private cruises can be found here.

12 Trees

To witness a modern interpretation of the classic Christmas tree, visit the Gardiner Museum from November 18 through January 8. As Canada’s national ceramics museum, Gardiner has featured countless memorable exhibitions throughout the years. Among their most popular is the 12 Trees exhibition, which has been a Toronto tradition for the past 27 years. This year’s theme, Good for the Earth, challenges artists to think outside the confines of a traditional tree, and will feature Christmas tree designs made of recycled and sustainable materials.

Travel Tip: Admission to the Gardiner Museum is half-price on Fridays from 4-9 PM.


What better way to gear up for the holidays than by catching a performance of a classic Christmas stage performance?  This winter, Toronto theatres will be hosting performances of timeless favorites like The Nutcracker and A Christmas Carol, as well as exciting live concerts by world-renowned artists such as the electrifying holiday-rock icons, Trans-Siberian Orchestra. Whether you’re looking to give a one-of-a-kind Christmas gift, or simply want to enjoy the show for yourself, a live theatre experience during the holiday season is one like no other. For a full list of holiday shows as well as ticket info, click here.

Mississauga Symphony Orchestra

If you’re that person that starts blaring Christmas music as soon as Thanksgiving ends, then seeing a performance by the Mississauga Symphony Orchestra during the holiday season is a must. This December, the MSO will be putting on their seasonal performance titled, A Merry Little Christmas. Including everything from orchestral masterpieces like “Winter” from Vivaldi’s The Four Seasons, to holiday radio favorites like Sleigh Ride, an evening with the MSO will have you humming along to Christmas songs even after the snow has melted. For show and ticket information, click here.

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