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When you think of places to go for a winter vacation, Toronto is probably NOT the first place that comes to mind. If you’re like most people, you probably think of either ski resorts or escaping the cold somewhere South. Admittedly, aside from New York, a lot of cities aren’t exactly on my radar this time of year either…but somehow, I found myself closer to the North Pole than I’ve ever been and not even mad about it. If you want to have the best winter vacation in Toronto, this blog post covers Christmas markets, places to shop, restaurant/bar recommendations, tips on how to navigate the city for first-timers, and more.

First things first: Toronto is underratedespecially during the holidays.

Truthfully, I never really thought about coming to this city until I had to re-book and re-plan my entire European Christmas vacation (it’s a long story, and quite frankly, not worth my time to type it + your time to read it). All you really need to know is that when my awesome friend Lance suggested I to go to Québec City to see their (still European) Christmas markets, I sat down to book my trip and thought “what the hell, why not also check out Toronto?!”

  • To read the Québec City blog post that discusses how to spend 2 days in this wonderfully unique city for the holidays, click here

So I did. And I’m SO GLAD I did. After 3.5 days spent in the heart of downtown, it’s safe to say that the kindness of the locals, endless food options, holiday charm, internationally recognized Christmas market, and overall city vibe has put Toronto on my list of North American cities to brag about. Want to have the best winter vacation in one of my newest favorite cities? Keep reading…

Full confession: This was originally supposed to be a 3-full-day itinerary post. But after spending 3 & 1/2 days in Toronto searching for the best things to do in winter, I concluded that my top suggestions involve things to do when it gets dark: Christmas villages all lit up, seeing a holiday light display at a historic castle, a haunted steakhouse that doesn’t open til 4…you get it.

I know what you’re thinking….how do I choose? Well – that one’s up to you. I’m merely here to provide you with suggestions, photographic content, and my own personal opinion.

Jump to Section:

Toronto Fun Facts
Getting There/Getting Around
Best Christmas Things to do in Toronto
Must-Try Restaurants and Bars
Shops & Areas to Explore
Other Suggestions

Website Disclaimer: I visited Toronto during the 2022 holiday season. Although everything is accurate as of the publication of this post, it is important to keep in mind that prices, attractions, and other things may change with time.

But First: Toronto Fun Facts

I love chatting up the locals wherever I go. I find this is one of the best ways to learn about a city from an authentically real perspective. A few fun facts that I learned about Toronto from the people I met there are:

  • Currently, Toronto is ranked as the #1 most multicultural city in the world, with most of its residents being born outside of the country.
  • Toronto is one of the top destinations for filming TV shows and movies. (When I was there, they were filming Stranger Things near King Street!) Keep an eye out for New York cabs – wherever you see them parked, this clues you in that it’s a filming location.
  • Yonge St. in Toronto holds the record of being the longest street in the world at 56 km.

Toronto: Getting There/Getting Around

Getting There

  • The main airport to fly into for international flights is Toronto Pearson International Airport (YYZ). Travel time from the airport to downtown can range anywhere from 20 minutes to over an hour, depending on traffic.
  • Location-wise, I stayed at the Holiday Inn on Carlton St. in Downtown Toronto. Although this was a great location and had a subway station within walking distance, I found myself having to Uber a good bit to get where I wanted to go in a reasonable amount of time.

Getting Around

  • Transportation is by far my least favorite thing about Toronto. Traffic is horrible, and the subway/rail system isn’t super built up and somewhat unreliable. Many times, I found that the subway/buses/streetcars were delayed from the time it gave on my transit apps.
  • I spent about 50% of my time Ubering around Toronto, and the other 50% on the TTC (Toronto Transit Commission – aka, subway, bus, or streetcar). That’s not to say Toronto isn’t walkable – it’s definitely walkable depending on the area. But a lot of the things I wanted to do required me taking some other form of transportation in addition to walking.
  • You are able to purchase a PRESTO card for the TTC, which you can load money on and use on any form of public transportation. You can also purchase 1 trip, 2 trip, and all-day individual tickets.
  • In terms of taking the TTC, I felt like I had to utilize the buses/streetcars more than the subway due to the subway not having routes to where I was wanting to go. This was another downside for me, as I find the subway system easier to navigate than the buses.
  • Finding the right location to wait for buses/streetcars can be confusing. Often times, I would be standing on a street corner, and there would be a bus stop on each side of the street, plus one adjacent to the street I was standing on. Some of them have the bus route shown; others do not. Many times, I had to ask people nearby if I was standing at the correct stop because it wasn’t always obvious.

Best Christmas Things to do in Toronto

Distillery Winter Village

  • Dates: Nov 17 – Dec 31, 2022
  • For a complete list of dates/times, plus to purchase tickets, check out this page on the Distillery Winter Village website
  • Note: Tickets are only needed Friday, Saturday and Sunday after 4pm

This one is an absolute must. The Distillery District – a rustic-chic area in Downtown Toronto – is transformed into a winter wonderland that gives the feeling of a traditional European Christmas market. Known as The Distillery Winter Village, it captivates all who visit with thousands of string lights, carolers, and a massively huge Christmas tree. They have vendors selling everything from food and drinks to fuzzy socks, hats, and other Christmas gifts. You could easily spend half a day here (or even longer!) if you wanted to.

The main Christmas tree in the Distillery Winter Village Christmas market in Toronto, Canada

I (shamelessly) loved it here so much that I went twice during my time in Toronto. The way they have the market set up is so beautiful that you could walk around for hours and never get bored. In case you still aren’t convinced, The Distillery Winter Village recently received global recognition on 2 different international lists of the best Christmas markets in the world.

Distillery Winter Village also has countless shops, restaurants, cafes, and bakeries to choose from. In addition to the market vendors, the shops span everything from small clothing and gift stores to larger stores that have a little bit of everything. For food and drink, I was only able to personally try 3 places (2 restaurants and a brewery, which you can read more about in the Bars & Restaurants section of this post). If I could, I would spend an entire week just eating and drinking my way through the village. For a full list of shopping and dining options, click here.

Nathan Phillips Square

Dates: Nov 26 – Jan 7

Nathan Phillips Square is located in the heart of Downtown Toronto, right next to Toronto City Hall. This is where the famous ice skating rink and massive “Toronto” sign is located. You can rent skates for $15 (or $10 for kids!) and skate for up to 2 hours. For those that like the ambiance of skating in the evening under city lights, you can rent skates in the evening up until 9:45 pm. For more information on skate rentals, click here.

Ice skating at Nathan Phillips Square in Downtown Toronto

During Christmastime, Nathan Phillips Square also hosts the Cavalcade of Lights until 10pm. Tunnels adorned with Christmas lights, a huge Christmas tree, and Christmas market vendors bring the area to life. It’s fun to sit and admire everything all lit up while watching the ice skaters in the background.

Although Nathan Phillips Square is one of the main “Toronto tourist attractions,” if you have to choose between this and Distillery Winter Village, I would absolutely pick Distillery.

Casa Loma – Christmas at the Castle & Holiday Lights Tour

Dates: Variable; check out their website linked below to see dates/times and purchase tickets.

This one is another absolute-must. Casa Loma is full of history thanks to it’s original owner, Sir Henry Pellatt, but you know I went there for the Christmas decor and outdoor holiday lights show. *shrugs*

When purchasing tickets, there are a few different options to choose from. It is worth noting that the ONLY way you are able to tour the inside of the castle at Christmastime AND see the holiday light display outside is to purchase the “Christmas at the Castle” ticket and then do the “Holiday Lights” add-on at checkout. Furthermore, you are only able to do the Christmas tours certain days of the week, and the Holiday lights tour specifically starts after 5pm. Click here for more information and to purchase tickets.

The view from the top of Casa Loma in Toronto, Canada
View from the Norman Tower

If you can only do one or the other, I would recommend choosing the Holiday Lights tour. It takes you through the gardens in the back of the castle, into an underground tunnel, and finally to the stables where you meet Santa Claus. Just when you think it’s over, there is more to see. The amount of detail and effort that went into creating this winter wonderland is unmatched.

Admittedly, none of the photos that I took of the Holiday Lights outside did them any justice. For videos of the lights, in addition to other travel photos, check out my Instagram account.

Miracle Pop Up: Toronto

Dates: Nov 18 – Dec 31, 2022
Location for 2022: 875 Bloor St. West

I debated putting this under the restaurants/bars section, but since it’s uniquely Christmas, I decided to include it here. Miracle Pop Up is a company that puts Christmas pop-up bars in cities across North America. The menu is mostly holiday themed drinks that are served in souvenir mugs. Oh – and they have drag queen shows on select dates. It is festive, fun, and tacky in the best way. For more information including the drink menu and to make reservations, click here.

Must-Try Restaurants and Bars in Toronto

If I could have one superpower in the world, it would be to go to a “foodie” city and be able to eat all day long without ever getting full. While in Toronto, I was overwhelmed with the amount of restaurants, bars, and coffee shops that I wanted to check out. Below, a few of my favorites:

Old Flame Brewing Co.

Located in the Distillery District, Old Flame Brewing Co. is the perfect spot to grab a beer and warm up from the cold. They brew the most awarded craft lager beer in Canada, but it turns out there’s way more to this brewery than just the beer that makes it special. Outside boasts a rustic aesthetic that initially drew me in, but inside, there’s a reason behind literally ALL of the art and decor. The pillars have the brewing process painted on them, and the couches look like they’re straight out of your grandma’s living room. But it works. Plus, the space that it’s located in used to be an old abandoned alleyway in between 2 buildings. (Fun fact: they’re known for putting breweries in places that aren’t supposed to be breweries: another one of their locations is set in an old fire hall!) Seriously – go for the beer and the creativity.

The Keg Steakhouse + Bar – Mansion

A great way to practically guarantee that I’ll check out a bar or restaurant is to tell me that it’s located in a haunted building. There are multiple Keg Steakhouses in Toronto, and even though I’ve only been to the Mansion location, I’m convinced it’s the coolest. Pair the Victorian aesthetic with the holiday decor and ghost stories and you’ve got yourself the perfect dinner reservation. Plus, the food was phenomenal. Ask your server/bartender about their paranormal experiences – almost everybody that works there has had one.

Anywhere at the Fairmont Royal York Hotel

The most famous hotel in Toronto, the Fairmont Royal York has been graced by the presence of celebrities, United States presidents, and British royals, just to name a few. James Brown and Tina Turner have performed in the ballrooms. If you’re familiar with NYC, think the Plaza Hotel. It’s fancy.

Two of the main bars, The Library Bar and Clockwork Champagne & Cocktails, have fantastic drink menus and small food bites. During Christmastime, the Fairmont Royal York has a holiday-themed bar – The Thirsty Elf – on the mezzanine floor (I admittedly didn’t get to check out this one as it was VERY crowded). For more of a sit-down meal, check out Reign (next to Clockwork Champagne & Cocktails), a Canadian brasserie which features French-inspired dishes.

  • The photos I took of the Fairmont Royal York do NOT do it justice. If you are in Toronto, it is a must-see hotel, even if you just go in to walk around. It is stunningly beautiful, especially at Christmas.
Clockwork Champagne & Cocktails bar at the Fairmont Royal York in Toronto, Canada
Clockwork Champagne & Cocktails at the Fairmont Royal York

And A Few Others….

The bars & restaurants highlighted above all have either a history or something specific that I felt inclined to point out, but they were far from the ONLY good places I ate. Below are my other favorites:

  • Madrina Bar y Tapas – Distillery District (Barcelona-inspired tapas restaurant)
  • Cluny Bistro & Boulangerie – Distillery District (BEST French onion soup of my life!!)
  • Aroma Espresso Bar – King Street West (cafe with coffee, baked goods, and more in a modern-yet-retro-glam space. At the time, their website was undergoing construction, so I did not link it).
  • The Mission Eatery – Queen Street West (Asian/American hybrid that has practically all 5 star reviews)
  • Pravda Vodka Bar – Wellington Street (upscale Russian-inspired bar with a DJ and glass walk-in vodka freezer)
  • Playa Cabana – Dupont St (Mexican restaurant serving primarily tequila and mezcal; if you like spicy margs, they make the BEST!)

Toronto Shops & Areas to Explore

Toronto Eaton Centre

The largest shopping mall in Toronto, the Eaton Centre is a great place to spend the day if you want to get out of the cold. They have countless stores and restaurants to choose from, and it is (of course) decorated for Christmas in the wintertime. Hardcore shoppers could easily spend half a day here if not more.

Yonge-Dundas Square

Similar to Times Square in NYC, Dundas Square is lit up with live billboards, city lights, and a bustling plaza. Located right across from Toronto Eaton Centre, the Square is an area where a lot of events take place, from concerts to festivals and more. When I was there, they had a large Christmas tree in the center and music playing nearby. I was also lucky enough to catch a winter snowfall here my first night in Toronto!

Dundas Square in Toronto Canada
Dundas Square at night in Toronto, Canada

Queen Street West / King Street West

Queen Street West was probably my favorite street I walked down. It had an abundance of cute coffee shops, restaurants, and stores. The Mission Eatery is a good landmark to put in that will take you close to many shopping and dining options (bonus: they also have great breakfast!). King Street West is parallel to Queen and located a few blocks south. In the words of my Uber driver, King Street is for the 20-something’s who want to party, and Queen Street is for the 30-something’s that want a more chill vibe.

There were an abundance of surrounding streets near King and Queen that had cute shops and restaurants too. Notable areas include the intersection of John and Richmond, the intersection of John and Queen, and the intersection of Adelaide and Richmond St.

View of Queen St. West in Toronto Canada

Yorkville Village

This is the high-end section of town with a lot of expensive stores. The Louis Vuitton store is a good Google Maps landmark that will take you to the heart of Yorkville. This area is NOT a must-do, IMO, but if you have extra time, it’s fun to go walk around – especially when it’s decorated for Christmas.

The Path System

Similar to the Pedway System in Chicago, Toronto’s Path System is an underground walkway spanning more than 30 km. Another great way to spend your time while getting out of the cold, The Path offers restaurants, shops, and more, all while connecting to various buildings, subway stations, hotels, and tourist attractions. Click here for more information and to download a map of the Path System.

Kensington Market

Known as a “hippie, artsy neighborhood,” Kensington Market is known for having eclectic bars, restaurants, shops, and more. I spent an afternoon walking through here, but to be honest, it seemed pretty run down. Perhaps there was a better part of this area that I didn’t know about? There were a couple cute places that I saw, but overall, this is not a must-visit neighborhood IMO, especially if you had limited time in Toronto.

Other Suggestions

I didn’t get to do any of the following things listed, but throughout my 3.5 days in Toronto, they were suggested or mentioned to me by many people:

  • The CN Tower – Toronto’s famously high tower offers sweeping views of the city. There is also a restaurant at the top – The 360 – which allows you to have dinner overlooking the city lights. Click here to read the menu, to make reservations, and more.
    • This is one of the things I really wanted to do, but unfortunately ran out of time.
  • Check out a sports game – Toronto is a HUGE sports city, with the most popular sport, of course, being hockey. In the winter, there are many opportunities to catch a Toronto Maple Leafs game, and watching the Toronto Raptors play basketball is also popular. If sports tickets (like everything else right now) happen to be outrageously priced, check out this website that lists some of the best sports bars in Toronto.
  • Take a day trip to Niagara Falls – Get Your Guide offers tours to Niagara Falls that you can book using this link. (Bonus: these tours are usually cheaper in the winter!)

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