Toronto Winter Weekend Itinerary

Toronto Winter Weekend Itinerary

Since I’m leaving Toronto (and winter) behind to head to New Zealand tomorrow, I decided to write an itinerary for spending a winter weekend in Toronto.

Winter in Toronto is a special time. The city comes alive in the winter with outdoor skating rinks literally everywhere. Tobogganing takes over every hill, no matter how small. We’re fortunate to get sun with our snow, and to have underground tunnels to avoid the freezing days.

Sure, it can be cold. But Toronto makes up for it with a lot of interesting things to do.

So, how should you spend a winter weekend in Toronto?


Friday Night

Start your winter weekend in Toronto with a visit to the Royal Ontario Museum (ROM). On Friday nights, the ROM hosts “Friday Night Live.” At these events the galleries are open, but a dance floor is added. It’s probably the only time you’ll ever get to dance in a museum (without looking crazy).

From 7p.m. on, you can visit the ROM for just under $20. Get there early, as spots are limited. It helps to buy tickets online.

You must be 19+ to go to Friday Night Live.

Toronto Winter Weekend Itinerary

Saturday Morning

Start your day by heading to the St. Lawrence Market in Downtown Toronto. In 2011, it was rated the best food market in the world by National Geographic. The St. Lawrence is a Toronto institution that features quality meat, produce and baked goods.

Toronto Winter Weekend Itinerary

I recommend getting there early (around 8 a.m.) to snag some chocolate croissants from the lower level. Pair that with a coffee from the famous Balzac’s Coffee Roasters across the street (or apple cider if, like me, you don’t do caffeine) and wander the market while you eat your breakfast.

Bring reusable bags if you want to grab some snacks for later in the day. You can find local cheese, crackers, olives, nuts, sweets and more at the St. Lawrence.

Save some room for the official food of Toronto: a peameal bacon sandwich. The best ones are from Carousel Bakery.

Carousel Bakery used to only bake bread and serve their peameal bacon sandwiches as samples. They quickly realized that people were coming more for the peameal, so they switched their business plan.

If you’re not from Canada, you may know peameal as “Canadian bacon” or “back bacon.” Here, it’s served fried on a bun. Add some mustard or honey to complete this Toronto delicacy.


Saturday Early Afternoon

From the St. Lawrence Market, take the TTC or walk 30 minutes to the Art Gallery of Ontario (AGO). The gallery features art by the Group of Seven and indigenous artists, amongst others.

The AGO is a must see while you’re in Toronto, even if you’re not very into art. Skip the extra exhibit and head to the second floor to a glass and wood room that stretches the length of the building. Take a seat on a bench and look out at the winter landscape. It’s a one of a kind view. There’s even an espresso bar if you want a snack.

Tickets are only $20 for adults. The AGO is open until 5:30p.m. on Saturdays.

Toronto Winter Weekend Itinerary


Saturday Late Afternoon

When you’re done at the AGO, head over to the famed Distillery District. The red brick style of the Distillery makes it a beautiful place to walk. It is like a piece of Europe in Toronto.

There is an eclectic mix of stores if you’re looking to do some shopping.

In the winter, there is nothing better than wandering the Distillery District with a hot chocolate from SOMA. It is the best chocolate place in the Distillery – maybe even in Toronto. If you think you can handle it, get the Mexican hot chocolate for a bit of added spice! Before you leave, stock up on chocolate bars and truffles to take home (if they make it that far!).

In November and December, the Distillery District transforms into Toronto’s most popular Christmas market. They put up a massive Christmas tree, decorated with a blinding amount of lights. Bands play music every day (Saturdays feature pop music). Warm up at a beer garden with glüwein, hot toddies or beer. Check out the vendors that sell knitwear, ornaments, soap and food.

The Distillery District is free to enter, but the Christmas market costs $6. Book online to get an admission time slot and skip the line. Once you’re in, you can stay for as long as you want.

The Christmas market runs until 9p.m. It typically runs from mid-November until December 23rd.

Toronto Winter Weekend Itinerary


Saturday Evening

If you’re hungry, head over to Boku Noodle Bar for Japanese, El Catrin Destileria for Mexican or Pure Spirits for excellent oysters.

Take in a show at Soul Pepper, the theatre company in the Distillery District. The theatre is smaller and does unique performances like A Christmas Carol in theatre in the round.

This winter, Soul Pepper is performing A Christmas Carol and Peter Pan.

Tickets are much more reasonable than other shows in Toronto. See their schedule and pre-book tickets here.


If you’ve had your fill of the Distillery District, head to Ripley Aquarium.

Book Sharks After Dark tickets and plan to get to the aquarium after 7pm in order to save a few dollars on admission. Adult Shark After Dark tickets cost $30. The aquarium is open until 11p.m. so there’s no rush (and less of a crowd), making it the perfect time to visit.

Ripley Aquarium is a great winter spot, because it doesn’t matter if Toronto is freezing or dark.

My favourite part is the Dangerous Lagoon, an automated walkway that winds you through (and beneath) the shark tanks.

Toronto Winter Weekend Itinerary


Sunday Morning

What better way to start the day than with brunch?

If you’re feeling classic, head to School in Liberty Village. The brunch is so amazing, you’ll be ok with going to school on a weekend (bad joke aside, the food is seriously impressive!).

Brunch starts at 10a.m. School doesn’t take reservations, so you may have to wait a bit for a table. The earlier you get there, the better.

If you’re looking for a more interesting breakfast, head over to Rol San in China Town for the best dim sum in Toronto. The food is very reasonably priced (i.e. 4 dumplings for $6). The menu is more of an order form, but it has English names for each dish. If you don’t know what they are, take a shot in the dark or ask a server for help.

Rol San opens at 9:30a.m. They don’t take reservations. Try to get there no later than 11a.m. to avoid the rush of hungover students looking for a (delicious) cheap breakfast.

If you eat at Rol San, wander across the street to Kensington Market before you leave. Kensington is a historical district with some interesting shops to explore as you work off brunch.

Real Food


Sunday Early Afternoon

On your last afternoon in Toronto, head to Nathan Phillips Square. It is now the site of the Toronto sign, but it has long been home to an open air skating rink in the winter.

This is a great activity for friends, couples, families or just you! Even Torontonians head downtown to skate at Nathan Phillips Square every winter.

Didn’t bring skates? No problem! Rent them for $10/two hours. Helmets only cost $5/two hours. The rental stand is open from 10a.m. to 10p.m. daily.

Warm up with Beavertails and hot chocolate afterwards.

Toronto Winter Weekend Itinerary


Sunday Late Afternoon

End your last afternoon in Toronto by warming up at the Elmwood Spa. Get a hot stone massage or a fire and ice body treatment to unwind after skating.

The Elmwood is open until 6:30p.m.

Services over $100 grant you free access to the swimming pool, whirlpools and steam rooms. They recommend arriving an hour before your services to full enjoy the pools.


Sunday Evening

For your final evening in Toronto, keep it simple and have a nice dinner.

Toronto has hundreds of incredible restaurants, but that’s a whole other blog post. So, I’ll just recommend three restaurants near downtown Toronto.

Chubby’s Jamaican is an adorable Jamaican themed restaurant on King St. The food is simple Jamaican fare done to perfection. Get the jerk wings and jerk chicken – you won’t be sorry! Everyone I know has either loved Chubby’s or is dying to go.

Make a reservation so you don’t get stuck waiting in a line. The prices are reasonable for Toronto ($19 for a main), so you won’t break the bank getting chubby at Chubby’s!

Toronto Winter Weekend Itinerary


Richmond Station is a restaurant committed to fresh, local ingredients. Because of that, it’s menu is often changing. They are well-known for their great wines.

The restaurant maintains its authentic neighbourhood eatery style, complete with limited seating. Make a reservation for dinner. Prices at Richmond Station are average for Toronto ($25 for a main).


Amano Pasta at Union Station is a delicious dinner option. They specialize in homemade pasta that may be the best I’ve ever had (outside of Italy, of course). Amano frequently changes its menu and warns you not to get too attached to the current fare. Try to get a seat near the pasta making area for some great entertainment while you eat.

Located inside Union Station, Amano is easy to get to from the TTC or the underground PATH system. The restaurant is on the smaller side, so make a reservation to be safe. The prices are very reasonable for such great quality pasta and rather large portions (about $20 for a main).


Toronto Hotel Tip

Stay in a hotel on the underground PATH system to avoid some of the cold weather. The PATH is a network of underground walkways that run throughout the downtown core of Toronto. It connects many offices, subways and other buildings. Inside the PATH, you can find shops, restaurants and more.

Some hotels on the PATH are the Fairmont Royal York, the Sheraton, One King West and the Delta.


As I mentioned, I head to New Zealand tomorrow so I’ll be skipping Toronto’s winter this year. I was almost sad about that until I started packing shorts and realized that it’ll be shorts weather at Christmas (is that even allowed?!).

So you’ll have to enjoy the winter weather for me!


What’s your favourite winter activity in Toronto?


29 thoughts on “Toronto Winter Weekend Itinerary”

  • I’d love a hot stone massage right now! It sure looks like you had a varied trip to truly enjoy your time in Toronto. Those Christmas lights are really getting me in the festive spirit and I’d love to visit myself.

    Hope you’re having a fab time in New Zealand! 🙂


    • I’ve been living in Toronto since I was born, so this was more of an amalgamation of my life here. I have crammed these events into a weekend before!
      Thank you very much, Jaz.

  • This was a timely post. I’m in the process of planning a trip to Toronto for my birthday in May. I like the itinerary that you shared.
    I am most likely gonna check out downtown and go ice skating. Woo hoo!

  • Have a safe journey to New Zealand. Loved this itinerary for Toronto and would want to experience winter there. Have lived in Detroit and think the winter here would be pretty much similar to Michigan due to proximity with Canada.

    • Thank you for the well wishes, Navita.
      Toronto is sort of lucky to be next to a large lake so our winters can actually be pretty reasonable. I’ve heard Michigan is actually worse than most southern Canadian winters (but I’ve never been). We also get beautiful sunny winters where it reflects on the snow that can be very beautiful (when it isn’t blinding you).

  • First of all good luck without your new experience in New Zealand, and as I am planning to go back to Canada in the next couple of years I’ll certainly keep in mind these tips!

  • I don’t live THAT far from Toronto, but still have never been! I wouldn’t have thought about visiting in the winter though because COLD. But I might have to change my mind! I would not mind wandering around the christmas market with a cup of the best hot chocolate in the city!

    • Definitely take the time to visit! There are lots of ways to avoid the cold (hot chocolate is probably my favourite). I think because people are worried about the cold winter can be the best time to visit – less tourists and more local activities to enjoy!

    • It’s been hugely popular since it opened. I spent last year touring German Christmas markets so I have to say winter is not complete without a good Christmas market visit!

  • These are very nice recommendations! Thanks so much for sharing. Never thought of visiting Toronto before, but it sounds especially magical in winter time 🙂

  • Wow! I’m shocked by all the things you can do in Toronto. That’s amazing!
    I’ll save this post for later, as Canada is on my bucket list.

    Thanks for the useful tips!!!

    Maria, from Argentina

  • Awesome recommendations! Only yesterday I was asking a friend about a trip coming up to Toronto and he told me only knew good food places lol I was perfectly happy to pig it out but might as well try out some of the places you recommended hehe. I am heading to NZ too in a week!

    • Thanks, Arunima! Send me a message if you’d like some more tips on Toronto. I highly recommend doing a food tour no matter what time of year it is (partially because eating is one of my favourite things to do).
      That’s awesome. I hope you have a wonderful time! What part of the country are you going to?

  • Great suggestions! It almost makes me feel that we’ll be able to enjoy a bit of winter while we watch you tell us about what you are up to in NZ’s summer!

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