Toronto in the Winter: How and Why to Embrace Canada’s Coldest Season

Toronto Skyline Photo: Anna Starpoli
Posted February 5, 2025
Even the dogs in Toronto wear coats. Whether you’re shopping on Yonge Street or in Kensington Market, puffers don’t just appear in one-of-a-kind vintage stores or the sprawling Eaton Centre mall. Rather, they also cloak Toronto’s dachshunds and greyhounds, who strut through the city as unphased as their owners. On a weekend in December, a particularly spoiled French bulldog dons an embroidered Maple Leafs jersey, not unlike Carlton — the hockey team’s polar bear mascot.
From November through March, Toronto undeniably bears a bone-chilling kind of cold, yet the temperature dissuades neither dogs nor people from getting outside. Instead, winter christens the city with a New Yorker’s urgency—it’s hard to dawdle when the weather gnaws and pinches — alongside blink-and-you’ll-miss-them opportunities, whether you’re stumbling into Yo-Yo Ma’s Music Garden or discovering a bookstore bar, artisan market, or a seasonal pop-up.
Below, you’ll find the tourist’s ultimate toolkit for not only surviving but also thriving in a Toronto winter.

Toronto Neighborhood Rink Photo: Anna Staropoli
The Great Outdoors
“They should make coats for our legs,” my boyfriend quips as we start our Toronto weekend in Trinity Bellwoods Park. Though we’re walking briskly, we pause when we run into an ice rink with a view of the city’s most notable landmark, the 1,815-foot-tall CN Tower. The neighborhood rink is one of many to grace Toronto’s parks and epitomizes the city’s dedication to making winter fun.
Free and open to the public, these pop-up rinks welcome anyone with a pair of skates. The Maple Leafs’ own William Nylander has been known to lace up for an impromptu game of pickup hockey. Beyond these park arenas, you can rent skates at The Bentway’s ice trail, beneath the Gardiner Expressway, as well as Nathan Phillips Square, site of Christmastime’s Cavalcade of Lights.

Badiali Pizza Photo: Anna Staropoli
Pizza, Poutine, and Peameal Bacon
I don’t spend too much time observing the skaters, not because of the cold but because of my stomach. I’m on a mission to start and end my Toronto trip at the city’s best pizzeria. And, dare I say, Canada’s best pizzeria. (Maybe, honestly, even North America’s.)
As someone who’s lived in Italy and lives for pizza, I’ve been obsessed with Badiali for years. The corner pizzeria on Dovercourt Road sells vodka sauce pies and slices — my favorite — as well as burrata, mushroom, cacio e pepe, and a slew of other varieties. There’s usually a short line, but the crispy New York-style crust topped with homemade sauce warrants the wait. Plus, there’s no better hiatus from the wind.
If you’re looking for a sit-down meal, however, grab no more than a slice. Then, head to KŌST on the 44th floor of the Bisha Hotel. The California-inspired restaurant does brunch, lunch, and dinner, but in the wintertime, they also run a pop-up chalet with a French and Canadian-inspired menu. The rooftop’s chalet takeover seats guests at wooden chairs and plush couches overlooking the CN Tower, where fluffy blankets and Alps-esque decor create a ski lodge ambiance. Order the cheese fondue for the table alongside an amaretto-spiked chai or an apple cider and cinnamon mocktail.
Other culinary highlights? For a quintessential Toronto experience, don’t miss St. Lawrence Market for a custard tart from Churrasco’s and a peameal bacon sandwich from Carousel Bakery. If you’d rather something less Canadian, Daldongnae serves some of the city’s best-value Korean barbecue, with locations in multiple neighborhoods.
Meanwhile, Speakeasy XXX — the sister bar to Dutch-Indo restaurant Little Sister Portland — makes elaborate cocktails in a sleek, intimate environment. While you can order your standard Aperol spritz or martini, you’d be remiss not to try something you can’t get anywhere else, like the Ants on a Log cocktail with South American black ants.

Kost Restaurant Photo: Anna Starpoli
Cozy Up Inside the Fairmont
You could easily spread your time in Toronto across the city. But if you’d rather focus on one neighborhood, Downtown’s Fairmont Royal York does it all. Just across the street from Union Station, the luxury hotel transforms its lobby into far more than a meeting point. Its festive decorations are best appreciated from a table at Clockwork, the lobby’s restaurant. The kitchen excels in classics like hamburger sliders, as well as afternoon tea platters and photo-worthy seafood towers. For a nightcap, the adjacent Library Bar beckons with both intricate cocktails and desserts. Should you time your trip accordingly, don’t miss the panettone negroni from the hotel’s holiday pop-up, House of York.
The Great(er) Indoors
Not far from the Fairmont, you’ll find some of Toronto’s most beloved museums and cultural attractions. While Taylor Swift has already finished her six-show stint at Rogers Centre — home of the Toronto Blue Jays — Meridian Hall keeps the entertainment coming. The venue hosts comedy shows, concerts, and even Cirque du Soleil performances.
If castles are more your speed, head slightly north of the city’s downtown to Casa Loma. The preserved Gothic mansion highlights the mansion’s film history in its celebrity exhibit, while the building’s actual bedrooms paint the prettiest picture of life in the early 1900s.
And, of course, you have to experience a few Toronto classics at least once. Ripley’s Aquarium of Canada houses all kinds of sea life, from jellyfish to sting rays. Make sure to buy a joint ticket with the CN Tower. There’s nothing quite like the adrenaline rush from standing on the floor’s see-through glass — unless you brave the Edge Walk, which harnesses visitors on the outside of that 116-story tower.

Maple Leafs’ Arena Photo: Anna Staropoli
For the Win
One quick disclaimer: I live in Rochester, New York, and, like most residents of the state’s Western region, I’m a Buffalo Sabres fan, if only by community association. Yet like most people in Toronto, I can’t help but root for the Maple Leafs.
That’s because the city’s team spirit is infectious. Even when the Maple Leafs aren’t playing, hockey’s energy permeates Toronto. The Stanley Cup lives in the nearby Hockey Hall of Fame — a worthwhile pit stop even for non-sports fans. The museum is a walk through history, not just hockey history, replete with interactive games.
It’s on home game days, however, that Toronto balloons into its fullest, finest form. Crowds gather outside Scotiabank Arena to cheer on Auston Matthews from the outside screen. Inside the rink, child hockey players — dubbed “Timbits” after Tim Hortons’ miniature donuts — face off down center ice during intermissions.
As I watch my first Leafs game — fittingly against the Sabres — the crowd waves pennants in the team’s signature shade of saturated navy. I can’t help but think the blue resembles that of the Toronto skyline, and I find myself screaming for both teams.
The Leafs win.