From the title, it may seem like I have given myself an impossible task (the cold weather edition of visiting a city in Canada, really?), but in Toronto’s defense and from experience with many northern summers, the city is probably a very different place in the summer with an abundance of rooftop bars, open markets, outdoor events, a beautiful waterfront, and even a beach/dock fusion situation. So this fall/winter Toronto travel post focuses on what’s best for brief outdoor walks or activities with plenty of options to warm up inside.
I’ve just gotten back from my second 48 hours in Toronto and am very ready to share anchored & adrift’s cold weather guide to the city from dawn on Saturday to the first available airport train on Monday.
Arriving at Toronto Pearson from the U.S. is quick and easy (a passport scan here, a nod there, then waived through) and the UP (Union Pearson) airport express train runs every 15 minutes and will have you at Union Station in just 25 minutes. The train has free internet with a relatively good connection, but is quite overpriced- if you’re traveling in a group, it’s probably less expensive to share a cab than individually buy train tickets.
An enjoyable and efficient international weekend adventure hinges on minimizing your travel time and costs. If you plan to use the train to and from the airport, I recommend staying close to Union Station. There are no luggage lockers at Union, so swing by your hotel to drop off any bag that you are unable or unwilling to carry around.
Using an arrival at Union as our starting point, here’s what not to miss during your 48 hours in Toronto.
Morning: Head east down Front St toward the St. Lawrence Market in Old Town, where a vast amount of vendors sell your typical market selection of meat, fish, bread, and cheeses with dining options mixed in throughout both floors (the stairwell down is slightly hidden in the middle of the market). The a&a pick for breakfast? A creperie tucked into the back corner of the basement floor in combination with a smoothie from a neighboring juice bar. Or, head south down towards the waterfront. Walk along Lake Ontario with a view of the Toronto Islands and the small Billy Bishop Toronto City Airport, which has small airplanes and helicopters constantly landing and taking off right along the waterfront. Enjoy the waterfront park, including the HTO urban beach that includes cheery umbrellas and loungers in an unexpected plot of sand (HTO is a play on H2O as Toronto is abbreviated TO). Warm up with a hot beverage of your choice at one of the neighboring coffee shops. Alternatively, head to brunch at one of Toronto’s many happening brunch spots. Here are a couple of suggestions.

Lunch: On your first day in Toronto, you must head to lunch at the CN Tower’s 360 Restaurant. You can purchase a tower-only ticket, stand in line, make your way up the CN Tower, butt into people on the main observation deck, and then get hangry so you have to either eat at CN Tower’s casual food restaurant or leave and search for food, or you can pay a little bit extra to get your first the lay of the city in a delightful way- minimal waiting, a three course pris fixe menu, perhaps a glass of wine, a city that unveils itself for you as you dine, and a generally much more VIP treatment. While having dinner in this restaurant is sure to be romantic, there is much more to see during the day at lunch. The view is spectacular.

The restaurant rotates 360 degrees every 72 minutes, and it is an incredible sensation to be far above the tops of the highest financial district skyscrapers. The restaurant is 351 meters or 1151 feet up. Access to the LookOut and Glass Floor levels of the CN Tower are complimentary with the purchase of a prix fixe meal by each guest.
Make sure to make a reservation in advance, and bring some kind of camera.
On Sunday, head to Pearl Harbourfront for authentic Chinese dim sum. Order a la carte and/or pick anything that appeals to your palate that goes by on a cart.
Afternoon: There are two major ice skating rinks to check out in Toronto. One is by the waterfront, the Harbourfront Centre Natrel Rink, which holds various skate events in addition to general skating, and the ice rink at Nathan Phillips Square. The Harbourfront rink was featured on the digital work accompanying Toronto’s number 7 ranking on the New York Times’ “52 Places to Go in 2016” list.
If visiting in the fall, don’t miss Roundhouse Park, a preserved locomotive roundhouse, or a circular building with a turntable connecting to railroad tracks that could rotate to move locomotives that were being serviced. The park includes a miniature working train track that kids and adults can ride around in, as well as a collection of train cars and locomotives, the former Canadian Pacific Railway Don station, and the Toronto Railway Museum. Two vendors are also part of the complex- Leon’s Furniture and Steam Whistle Brewing, where you can pop in to taste the local beer and have a snack. The roundhouse was originally completed in 1931.

On one of your days, head to Dundas Square, the Times Square of Toronto as it was described to me, to confirm that yes, 2.6 million people live and shop in Toronto. That’s almost half of Finland! Stop in at Toronto Eaton Center, a vast shopping complex currently under renovation that welcomes around 1 million visitors per week. Also worth a popping into is the odd 10 Dundas East, another complex that seems very oddly arranged (and was flooded with zombies on Halloween a few months ago. More on that later). It’s primarily a movie complex, but to reach the movie theater you pass through a series of levels with random shops (like a seasonal Halloween store that was sealed off this month), a food court, and then finally the theater at the top. I’m not quite sure who designed it, but it seems strangely bare for the massive space it fills.
Evening: For dinner, international Toronto has a world of options. For a steakhouse, uber over to Keg Mansion. While Keg is a chain, this unique location operates in a renovated mansion, and has a casual yet intimate feel, and they know how to handle their steak. The celebrated Momofuku’s Toronto location is in a gorgeous three story building adjacent to the Shangri-La Hotel. Choose the Noodle Bar (get the Momofuku ramen with pork buns to start), the bar area, or make reservations for the top floor, which is Momofuku’s version of a steakhouse. Another option- stay in Dundas Square and head to Spring Sushi, on the top floor of 10 Dundas, for unlimited Japanese and Thai food with touch screen ordering and an understated casual-swanky feel. Having covered most of the food menu and their wine, you can get a good meal for great value with surprisingly good Sauvignon Blanc for the price. I leave it to any adventurous readers to try one of their cocktails. If you want something super casual put still different, Hot Star serves large fried chicken on Yonge Street as it does in the night markets of Taiwan, and when they say large, they mean a single chicken breast that is bigger than your face. Order the original with pepper salt and a strawberry soda (you do not need fries with this, trust me), and then marvel at the feat of cooking engineering.
Saturday Night: If you dined at Momofuku or Spring Sushi, head to Drake 150 to experience one of the Toronto Drake establishments (bar, hotel, general store) with inspired cocktails set to great tunes. The DJ actually works, not just pushing play on a playlist. After refined drinks and conversation, it’s time for the rail drinks and beers of Adelaide Street’s bars and clubs. Bar 224 has a $10 cover with $3 drinks inside with a busy dance floor in the basement. For clubs, continue down Adelaide for Uniun or ACE. If you’re up to expanding your night beyond walking distance, head to the Drake Hotel Lounge, the trendiest spot in trendy West Queen West.
If you get a chance to return to Toronto or stay longer, dig into its multicultural details like Little India or new art collections popping up around the city.
How to get there: Air Canada boasts an extensive range of destinations, and has sales during Cyber Monday and at the turn of the year where you can get a decent percentage of your flight costs off. West Jet is another major airline. Flying first thing on Saturday morning vs. Friday night typically saves you about $100.
Where to stay: For the above experience of Toronto, Le Germain Hotel Maple Leaf Square is ideally located with walking distance to the CN Tower, the waterfront, Dundas Square and other shopping, and of course Air Canada Centre. You don’t have to leave the building to buy any groceries or alcohol, anf breakfast and wifi is included. The New York Times Travel section recommends the Drake Hotel, which is very hip but also very far away from what I consider the center of Toronto. It’s a different kind of Toronto experience. To see their recommendations, click here.
This 48 hours post is just to give you a bearing of the city. I love feedback and any advice for more time in Toronto, or where to go during summer 2016. Let me know in the comments below!