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Guide to Making the Most of Fall and Winter in Toronto



If you’re not from Toronto, there’s a good chance you might’ve heard some not-so-nice things about the fall and winter in our city. And it’s not entirely unfounded. Toronto can be pretty chilly when the summer fades away.


But for those in the know, Toronto is a winter wonderland full of unique and exciting activities and destinations. Torontonians have learned not only to embrace the cold, but to celebrate it! And if you’re willing to join them in braving the temperatures, you’ll quickly learn that the city comes to life when it’s cold outside.


Here is our comprehensive guide on how to maximize your time in Toronto during the fall and winter.


Sharpen Your Skills: Toronto’s Best Skating Rinks

If there’s one thing there’s no shortage of during the winter in Toronto, it’s ice rinks. Whether a small sheet at a community park of one of the city’s exciting and elaborate rinks, there are a plethora of options to choose from.


The Bentway Skate Trail

A new and exciting addition to Toronto’s Fort York neighborhood, the Bentway Skate Trail is a community skating trail built underneath the city’s busy Gardiner Expressway. The Bentway represents the first step in a project designed to transform the space beneath the freeway into beautiful community space and is a must-see!


Nathan Phillips Square

Located at Toronto’s City Hall, the Nathan Phillips Square skate rink, home to the iconic Toronto light display, is the city’s biggest – and most photographed! – ice rink. Boasting a beautiful view of the city, a wide array of food vendors and Toronto’s official 60-foot Christmas tree, Nathan Phillips Square is a perfect place to go with friends or family.


Harbourfront Centre

Located on Toronto’s picturesque waterfront, the Natrel Rink at Harbourfront Centre is a favorite skating rink among Torontonians. Offering a beautiful view of the lakefront, it’s been a staple ice rink for nearly three decades. And on Saturdays during peak winter months, it’s home to the popular DJ Skate Nights – a popular and lively event that draws crowds of all ages.


Feel Like a Kid Again: Toronto’s Best Tobogganing Hills

There are few more iconic winters pastimes than tobogganing. And while you might think a big city like Toronto would be devoid of great tobogganing hills, you might be surprised! With a huge number of parks scattered throughout its reaches, the city has no shortage of great slopes.


Trinity Bellwoods Park

Located conveniently in Toronto’s Queen West neighborhood, Trinity Bellwoods is a family-friendly park boasting outstanding tobogganing hills. And when it’s time to warm up, the neighborhood is home to a huge variety of coffee shops and great restaurants.


Riverdale Park

In the city’s east end lives Riverdale Park. With its exceptional views of the city, it’s a great place to catch a glimpse of the big city while enjoying some outstanding tobogganing. Riverdale Park also features a community skating rink in case you’re in search of a variety of activities.


High Park

Spanning 161 hectares, High Park is one of the city’s municipal jewels. And while tobogganing is no longer allowed in certain parts of the park, it is still more than welcome in Howard Park, at Avenue Road and Parkside Drive, where you can enjoy a pretty thrilling ride. The park is also great for a full day of activities – as a mixed recreational and natural park, it includes sporting facilities, cultural facilities, educational facilities, gardens, playgrounds and a zoo.


Culinary Comfort: Must-Try Winter Food and Drinks

From a quick pit stop to warm up with some hot chocolate to food and drink festivals to the city’s best restaurants, Toronto has no shortage of great culinary options to help fight away those winter blues.


SOMA Chocolatemaker

With two locations, SOMA Chocolatemaker offers outstanding varieties of hot chocolate. SOMA designs and creates handmade chocolate in their “chocolate lab.” SOMA offers a fulsome chocolate experience and is a must-try when in the city’s Distillery District (32 Tank House Lane) or King West (443 King Street West) neighborhoods. We recommend the chili flake and orange hot chocolate!



Taking place each winter, Winterlicious is a food festival in which restaurants across Toronto offer a limited menu of prix fixe dinners at a discount from typical prices. If you’re looking for a great way to get out of the cold and sample some of Toronto’s finest cuisine without breaking the bank, Winterlicious is the way to do it. For details, check online at https://www.toronto.com/events/winterlicious/.


Winter Brewfest

Heading into its fourth year this year, Toronto’s Winter Brewfest is the city’s biggest indoor festival of beer. With everything from big brands to microbreweries, Winter Brewfest is a great way to get out of the cold and sample some outstanding beer – including some delicious, limited-edition winter batches! To learn more, check out https://www.toronto.com/events/winterlicious/


Winter Patios

In Toronto, fall and winter don’t mean the end of season – the city offers a huge selection of wintertime patios to keep outdoor dining alive through the chilly months. From the Broadview Hotel at 106 Broadview Avenue, a revamped hotel in the Riverside neighborhood which offers incredible views of the city, to The Drake Sky Yard at 1150 Queen Street West which embodies a Norwegian theme with everything warm, delicious and cozy, there are no shortage of options.


Warm and Cozy Restaurants

When the days are cold, there are few things better than a cozy spot to relax, warm up and have a great bite of comfort food. They say good things take time so if you’ve got a little extra time, the rustic Woodlot, located at 293 Palmerston, will perfectly cook a selection of seasonal dishes in the restaurant’s wood-fired oven. Or, check out Big Crow at 176 Dupont, for delicious seasonal BBQ dishes. The restaurant is said to be inspired by Algonquin Park and canoe trips and boasts a woodsy cabin aesthetic that sets the perfect backdrop for a cozy fall or winter meal.


Explore and Discover: Toronto’s Seasonal Outdoor Attractions

Toronto truly embraces winter, and that’s largely attributable to the vast array of outdoor attractions that take place through the fall and winter that embody the best of what the city has to offer.


The Toronto Christmas Market

A seasonal staple, The Toronto Christmas Market takes place every year in the city’s Distillery District and is rated one of the top 10 Christmas Markets in the world. Boasting a massive and beautiful Christmas tree, great spots to eat and vendors to shop, all set against a wintery brick backdrop, this is a great outdoor option to stop and explore.


The Toronto Light Festival

From January through March, The Toronto Light Festival lights up the long winter nights with distinctive works from local and international artists. This awe-inspiring visual spectacle lights up Toronto’s Distillery District and is a must-see attraction.


Winter at Ontario Place

Each winter, Toronto’s famous Ontario Place – a former theme park and exhibition grounds – transforms into a wonderland of winter activities. From skating to bonfires to delicious warm food and beverages, Winter at Ontario Place is a perfect way to pass a winter day in Toronto.


Winter Stations Design Competition

Entering its fifth year, Winter Stations is an international design competition which brings beautiful and inspiring temporary public art installations to celebrate Toronto’s winter waterfront landscape. Running from February through April, the theme of this year’s Winter Stations Design Competition is migration. Stop by The Beaches to see it all come to life!


Toronto Icefest

Taking place in the city’s cultural Bloor-Yorkville neighborhood, Toronto Icefest showcases incredible ice sculptures and spectacular ice carving demonstrations. Entering its fourteenth year, Toronto Icefest never fails to amaze.


A Touch of Culture: Indoor Events and Entertainment

If you’d rather stay inside and away from the cold, don’t worry. Toronto offers some world-famous cultural events and entertainment. Whether you’re into music, fashion, design or film, Toronto has something for everyone.


Toronto Fashion Week

Home to Canada’s most iconic women’s fashion designers and the next generation of emerging talent, Toronto Fashion Week shines a spotlight on fashion, art and culture with a global twist in a re-imagined bi-annual celebration. Taking place in Toronto’s Bloor-Yorkville neighborhood in September, Toronto Fashion Week is a true cultural experience, whether you’re a fashion connoisseur or just curious what it’s all about.


Winter Film Festivals in Toronto

If you enjoy cinema, then you’ll find something you love at one of Toronto’s many winter film festivals. From the Flashback Film Festival in February, to the Canadian Film Festival in March, to Doc Soup and TIFF Top 10 in January, to The Next Wave Film Festival in February, you can get your fill of everything from documentaries and classics to short and feature films.


The Canadian Opera Company

You can keep warm and enjoy a concert while basking in one of Toronto’s most breathtaking intimate spaces – the Richard Bradshaw Amphitheater. Located at The Four Seasons Centre for the Performing Arts at 145 Queen Street West, the amphitheater offers free concerts presented by The Canadian Opera Company, all winter long.


Toronto Offiste Design Festival

Taking place in January, this ten-day design festival is Toronto’s biggest not-for-profit design activation. With over 100 free events and exhibitions, Toronto Offsite Design Festival turns the city into a hub for creativity, taking design and art out of the studio and into the urban environment. The festival is among Canada’s most well-known, attracting over 140,000 visitors annually.


Warm Up and Unwind: Toronto’s Best Spas and Steam Rooms

What’s better than a hot steam room to warm up and relax on a cold day? Toronto is home to some world class spas and steam rooms to help you unwind and recharge.


Hammam Spa

Located at 602 King Street West, the Hammam Spa offers traditional Turkish baths. A first of its kind in Eastern Canada, it offers a steam room filled with both cool and hot air followed by a bath on a 108-degree marble table.


Sanduny Spa

This beautiful North York Spa has a few key rules: take your time to relax, and then enjoy a cold plunge when you’re finished. Located at 1027 Finch Avenue West, Sanduny Spa offers a great option without having to venture downtown.


Winter Weather 101: How to Dress for Toronto Fall and Winter

With the right selection of attire, fall and winter can be an amazing time of year in Toronto. The key is choosing the right clothing before you leave the hotel.


In the fall months, think warm coats, rain jackets and sweaters. Fall in Toronto is a beautiful time of year. While brisk, the air is crisp and fresh without being too cold.


The winter can be much cooler – dropping as low as -20 degrees – but is equally as beautiful and enjoyable. Warm boots are key, and so is a warm winter jacket. Wearing gloves, earmuffs and warm hat and crucial in enjoying the winter in Toronto. Believe it or not, you lose most of your body heat through your head and your feet!


The Roehampton Hotel is Happy to Help

As a proud Toronto establishment, The Roehampton Hotel is pleased to provide its guests with valuable and helpful insight to ensure they get the most out of their stay and are eager to provide the best experience possible. If you have any questions about where to go in Toronto, don’t hesitate to ask – our staff will be more than happy to help!


To learn what else the city has to offer, visit theroehamptonhotel.com/guides for even more of The Roehampton Hotel’s comprehensive Guides to Toronto.


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