Plan your ultimate winter escape to Toronto! This guide is packed with insider tips on where to skate, shop, and explore with your family. Discover festive markets, cozy cafes, and unforgettable experiences.
Looking out over the city from the rooftop of the Chelsea Hotel in downtown Toronto, I couldn’t help but feel the spirit of the season. A light dusting of snow was beginning to cover the rooftops and cast those beautiful beams from every streetlight and neon sign in this city of lights.
I love this city, from the family-friendly summer excitement of the Toronto Islands, Queen Street with its quirky stores and endless live music venues, to the incredible food of Kensington Market. But winter in Toronto? That’s pure magic. Winter villages, skating trails, holiday lights – it takes on an entirely new light. And I was here with my family to experience the best of it.
Strolling in from the street into the lobby of the Chelsea Hotel, my kids dusted the snow off of their shoulders and shook the outside from the pom poms on their toques. I sat down to take my jacket off when a friendly voice called over, asking if I wanted my picture taken. It was Daniel, the Chelsea’s friendly Bell Captain, a gentleman who has graciously helped me out on nearly every visit I’ve made to Canada’s largest hotel.
Wondering what brought him my way, I looked around and realized that I was sitting smack in the middle of the hotel’s Santa display, and here I was in the big man’s seat.
The whole lobby was decked out in full seasonal regalia. Santa’s, trees, reindeer, a motley crew of gingerbread houses wrapped by a working toy train. Part of a yearly competition between the hotel’s staff where guests can vote for their favorite design.
After checking into our room, situated in a wing of newly renovated suites, we unpacked and set about strategizing how to tackle our Toronto winter visit.
Toronto Skating Trails
With a plan in place and our cozy room waiting, we set out to explore the winter wonderland of Toronto, starting with hitting the ice. Now, I’m not shy about my family being a hockey family. Both Cohen and Dylan play rep hockey for our hometown of Brampton. So whenever we do any winter travel, we’re always looking for a place to strap on our blades and go skating. Luckily for us, Toronto winters offer a plethora of ice rinks and skating trails that are nearly as numerous as the city’s shawarma spots.
Just a short walk from the Chelsea is the Barbara Ann Scott Skating Oval, a small but popular outdoor rink tucked in behind College Park at College and Yonge. Many visitors to Toronto will head to the popular new Bentway Skating Trail beneath the Gardner Expressway by Old Fort York. But this would be my boys’ first time skating in Toronto (we can’t count our time at Celebration Square during our winter in Mississauga), So we wanted something epic.
We strolled down Bay St. to Queen St. and tied up our laces in one of the most iconic Ontario skating spots outside of the Rideau Canal in Ottawa. Nathan Philips Square at Toronto City Hall. This is, arguably, Toronto’s most popular outdoor skating rink. With the famous Toronto sign and the semi-circular Toronto City Hall as its backdrop, it was the perfect place to stretch our legs.
Downtown Toronto Shopping
Let’s face it: if you’re visiting Toronto in the winter, especially around the holiday season, shopping is probably on your mind. Just a casual stroll from both our hotel and Nathan Philips Square is one of Canada’s premier shopping malls, the granddaddy of them all, the Toronto Eaton Centre.
We took part in a little retail therapy. Some popular Roots hoodies for the boys, new luggage set for Christina, and me, well, I prefer to do my shopping abroad, so I took on sherpa duties and lugged the skates around (and maybe stopped for a cookie at Butter Baker Market).
Of course, shopping in Toronto isn’t limited to the Eaton Centre. This city has loads of great areas to spend your money. There’s Bloor-Yorkville, with its posh shops and artisan everything. Or Queen West, which I mentioned earlier, where quirky shops mix with high-end brands. If you love cool stuff, don’t miss Geologic. This store is Cohen’s favorite and has everything from dinosaur bones to crystals. It’s an adventure every time we visit.
Yonge-Dundas Square
During the summer months in Toronto, Yonge-Dundas Square is packed shoulder to shoulder for free outdoor concerts and events. But the fun doesn’t stop when the snow starts falling. During winter, Yonge-Dundas Square transforms into a winter wonderland. This city square, kitty-corner to the Eaton Centre, was transformed into a dazzling winter wonderland, with festive decorations and lights strung across the buildings.
Yonge-Dundas Square (renamed Sankofa Square a couple of years ago) cycles through displays in an endless cavalcade of entertainment. But during our visit, it was set up like a winter fair, complete with merry-go-rounds just like the ones we experienced at the Helsinki Christmas Market. You can check out their event schedule here.
Distillery District Winter Village
One of the things that I love about staying at the Chelsea Hotel is that they always partner up with the hottest tickets in the city. During Labour Day Weekend in Toronto, they had a deal that included tickets to the CNE. during the winter, the Chelsea partners with the Distillery District Winter Village.
The Winter Village is, without a doubt, the top winter attraction in Toronto—lineups for tickets and a mad rush for entry. But the deal with the Chelsea Hotel made it easy. Think express passes and no wait times.
We wanted to be prepared for the adventure, so we wandered back to the hotel, rested up at the pool (Dylan can’t get enough of the indoor/outdoor waterslide), and dressed up in some warm clothes before catching a cab over to Toronto’s historic Distillery District.
Picture cobblestone streets and Victorian-era buildings decked out with twinkling lights. A massive Christmas tree in the center was a sight to behold. We wandered amongst the chaos, sipping on hot chocolate and checking out all of the little wooden huts selling every manner of unique gifts – perfect for finding something for Christina.
We stopped for some delicious snacks, and I even snuck off to the Mill St. Brewery for a quick pint of their Organic Ale while the boys were distracted by a giant gingerbread house. This place is a must for those looking for a Toronto winter getaway. It has something for everyone to enjoy.
Little Canada
We woke up late the next day. The boys were nursing a wicked sugar hangover, and I was wondering how a half-eaten turkey leg wound up in my backpack.
We wandered downstairs in our pyjamas to grab breakfast at the Market Garden, the Chelsea Hotel’s popular breakfast spot, and the boys asked for a little time in the hotel’s busy arcade. While they played, I wandered upstairs to the adults-only rooftop pool to do a few laps.
After we were all rested, we walked a block down busy Yonge St. to Little Canada, one of our favorite things to do in Toronto with kids. Little Canada is an immersive museum where you can explore Canada’s most iconic landmarks and landscapes in miniature.
Each one is meticulously recreated in tiny detail. They have everything from Niagara Falls, the CN Tower, Old Quebec City, the Rocky Mountains, and even the Maritimes. Each one is brought to life with tiny moving vehicles, trains, and even miniature people going about their day.
Hockey Hall of Fame
I might have mentioned that hockey is a big thing in my family. Between the boys and I, we’re on the ice almost every day of the week. It’s a passion that borders on religion. And the Church of Hockey is right here in Toronto.
We spent hours wandering around the trophies and displays that held memorabilia from hockey greats like Gretzky, Lemieux, Richard, and Orr. We planted a kiss on the Stanley Cup and then talked about our experience on the Sportscenter Broadcast Exhibit.
They say, “Don’t meet your heroes.” Well, this is as close as you can get without crossing that line.
We went to the basement and took turns measuring our shot speed (hot take, I didn’t win), and even strapped on the pads to make saves from virtual NHL players. It was a wild way to spend the afternoon. One that we’ll never forget.
Elm Street Bar and Lounge
Dazzled by our visit to the Hockey Hall of Fame, we walked back up Yonge St. to Gerrard and the Chelsea Hotel, debating who was a better team this year: the Leafs, the Jets, or the Knights. We were famished after a second day of Toronto Winter activities. Luckily, the hotel has a fantastic on-site restaurant called the Elm Street Bar and Lounge.
This upscale casual restaurant has a great selection of steaks, burgers, and a great beer selection. For an appetizer, I highly recommend their cauliflower bites. They’re just the right amount of spicy and crunchy. We laughed and talked about our winter adventures in the city, comparing which food was the most unique and which experiences stood out from the rest.
But as our friendly server brought over the dessert menu, Dylan’s head drooped, and he nodded off right in his chair. Our Toronto winter weekend had been a blast. Maybe even a bit too much!
I picked him up and carried him back to the room. Time for bed and a wrap on an amazing and fun-filled winter weekend in the big city.
Disclosure: This article was written in partnership with the Chelsea Hotel, Toronto. I want to thank them for their support. All opinions remain my own.
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