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Romantic Date Ideas When Visiting Toronto this Winter

The weather outside may be frightful, but what better way to beat the winter blues than to warm up with your special someone this winter holiday with a trip to the bustling city of Toronto!

Whether you’re searching for romantic destinations that foster the closeness in a relationship or something fun and exciting to do together in the six, there really is something for every couple.

From physical exertion to fun outings and romantic dates, here are our top recommendations to add to your to-do list when visiting Toronto this winter season.


When most people come to the big city, adventure isn’t always top of mind. But it should be. Toronto is so much more than just shopping and nightlife, and there are so many fun, physical activities to enjoy in the city.


Couple kiss while skating

Skating at one of Toronto’s many outdoor rinks is the quintessential winter activity for couples to enjoy a romantic date night under the stars.

Not only is it incredibly romantic, but it’s also a great way to be active and burn off all that hot chocolate.

Plus, finding a spot won’t be difficult, as Toronto has numerous outdoor skating rinks scattered all throughout the city.

Here are some of the best outdoor skating spots:

  • Nathan Phillips Square | Queen St. W
  • Grenadier Pond | High Park
  • Sherbourne Common | East Bayfront
  • Natrel Rink at Harbourfront Centre | Toronto Harbourfront
  • Colonel Sam Smith Skating Trail | Etobicoke
  • The Bentway Skating Trail | Fort York


While most people don’t commonly associate Canada’s largest urban centre with nature and taking in the great outdoors, there are in fact tons of scenic spots throughout the city perfect for a winter hike with your special someone.

Some of the best hiking/walking trails within the city of Toronto include:

  • Crother Woods Trail | East York
  • Waterfront Trail | Harbourfront
  • High Park Trails | High Park
  • Leslie Street Spit | Tommy Thompson Park
  • Don Valley Trail | Flemington Park

Pursuit OCR

There’s nothing like a little healthy competition to keep the sparks alive.

If you’re looking to get your adrenaline pumping and unleash your competitive side, check out Pursuit OCR, a 30,000 square foot indoor obstacle course located just outside of the city in Etobicoke.

Completing the course together is a great way to get moving and will help you learn how to work together as a couple to further strengthen your bond.

couple snowboards outside of Toronto

Skiing and Snowboarding

While you won’t be able to hit the slopes in the downtown core, Toronto has tons of great ski and snowboarding hills throughout the GTA.

The only catch is, you may need to drive a bit outside of the city, but if you and your partner are snow bunnies that are itching to hit some fresh powder, there are tons of spots to choose from, such as:

  • Earl Bales Ski & Snowboard | North York, ON

Has 2 ski lifts and 4 trails – 1 beginner and 3 intermediate – on 6 acres of land. Located approx. 30 minutes from downtown TO.

  • Mount St. Louis Moonstone | Coldwater, ON

Has 36 slopes, 9 chairlifts, and 3 carpets, and accommodates all skill levels. Located approx. 1.5 hours from downtown TO.

  • Hockley Valley | Mono, ON

Has 5 lifts, 15 trails, and 30 skiable acres. Half of the hills are rated as Black Diamond, with the remaining hills suitable for beginner and intermediate skill levels. Located approx. 1.25 hours from downtown TO.

  • Dagmar Ski Resort | Uxbridge, ON

Has 2 magic carpets and 18 runs with varied terrain for all skill sets. Located approx. 55 minutes from downtown TO.

  • Glen Eden | Milton, ON

Has 6 lifts, 12 slopes, 3 terrain parks, and a snow tubing park. Located approx. 1 hour from downtown TO.

  • Brimacombe | Orono, ON

Has 23 runs and trails for all skill levels, from beginner to expert, open for day skiing, along with 11 runs open for night skiing. Located just over 1 hour from downtown TO.


Looking to cut loose and have a good time without getting too physically active? We’ve got you covered.

Toronto Poetry Slam

For artsy types looking for a unique outing to help get the creative juices flowing, check out the Toronto Poetry Slam presented by the Toronto Poetry Project.

The twice-monthly spoken word competition is held at the Drake Hotel Underground in the trendy and eclectic Queen West neighbourhood.

One-by-one, poets take to the stage to perform their poems in front of a crowd and panel of judges who give each poem a score between 0 and 10. The last poet standing wins a cash prize and of course, bragging rights.

Toronto Christmas Market Lights at Night

Toronto Christmas Market

Considered one of the best holiday markets in the world, Toronto’s famed Christmas Market held in the Distillery District will not disappoint.

With hundreds of vendors selling unique and locally handcrafted products, family-friendly entertainment, twinkling lights, beer and festive mulled wine on offer, and of course Santa and his elves, the Toronto Christmas Market will make even scrooges and grinches fall in love with the holiday season.

The best part is that admission is free from Tuesday until Friday at 6 pm. An admission fee of $8.00 is charged on weekends and after 6 p.m. on Fridays.

The market runs from November 14 until December 22.

The Roundhouse Winter Craft Beer Festival

If you’d rather curl up with a cold pint instead of hot chocolate, The Roundhouse Winter Craft Beer Festival is where you will want to be.

Held outside the Steam Whistle Brewing in Roundhouse Park, the festival only showcases beers from Ontario Craft Brewers.

The festival will give you the opportunity to check out a total of 40 local breweries, get cozy by a campfire, roast marshmallows, and capture the moment with a photo station.

Plus, with a DJ dance party and games like bean bag toss, giant beer pong, giant Connect 4, and giant Jenga, there is sure to be never a dull moment.

Raptors Game

Three words: We. The. North.

What better date night activity for sports lovers than to catch the reigning NBA champions, the Toronto Raptors, play on their home turf?

Located just a short walk from the SoHo Hotel & Residences, catching a Raptors basketball game at the Scotiabank Arena after dinner out on the town is an absolute must when visiting Toronto.

DJ Skate Night

Think of Toronto’s DJ Skate night as regular old outdoor ice skating, but with a twist.

harbour view of DJ skate night in Toronto

Often described as Toronto’s coolest dance party, the weekly winter event always has a stellar lineup of DJs that will help to heat up your Saturday night skate.

Plus, if you get tired and want to take a break, you can get cozy by the fire pits sipping a hot drink from the rink-side café-bar.

Oh, and did we forget to mention that admission is completely free?

If a night of free skating under the starts to amazing music spun by some of Toronto’s hottest DJs sounds like your idea of a good time, check out the DJ Skate Night, which takes place at Toronto’s Harbourfront Centre every Saturday night from December 14 to February 15.


Looking for the perfect romantic date night that will send sparks flying?

You’re in luck. Here are some of the top romantic activities perfect for a magical date night in Toronto.


Calling all foodies – keep your belly warm and full by checking out Winterlicious, Toronto’s premier prix fixe food event.

Over 200 Toronto restaurants participate in the annual winter event celebrating Toronto’s epic culinary scene and offer a prix fixe program.

Three-course prix fixe lunch and dinner menus will be offered at $23, $28, or $33 for lunch and $33, $43 or $53 for dinner.

Along with the prix fixe promotion, Winterlicious also offers a series of ticketed culinary experiences.

Toronto lights festivalToronto Light Festival

It may be dark by late afternoon, but the Toronto Light Festival is sure to brighten up even the coldest of winter nights.

Held in the Distillery District, the festival transforms the historic neighbourhood into one of the largest open-air galleries in North America, showcasing stunning light art installations from local and international artists.

Pottery Classes

What’s more romantic then re-enacting the famous pottery scene from the 1990 movie Ghost?

Getting your hands dirty and finding a creative outlet can be a great bonding experience and makes for a much more romantic date night than the traditional dinner and a movie.

The Gardiner Museum offers drop-in pottery classes suitable for all experience levels every Wednesday and Friday from 6 pm to 8 pm and Sunday from 1 pm to 3 pm. Tickets are first-come, first-served, and go on sale just 30 minutes before each session.

Allan Gardens Conservatory by Candlelight

Re-enact your favourite Hallmark holiday romance movie with an enchanting evening walk through the Allan Gardens Conservatory by candlelight.

Every year at Christmas time, Allan Gardens puts on a magical Christmas display brimming with thousands of flowers and plants, including over 40 varieties of poinsettias, and stunning seasonal topiaries made entirely of plant material.

And to top it all off, admission is free.

Staycation at The SoHo Hotel

If you’d rather not brave the cold and prefer the idea of snuggling up indoors, why not make a weekend of it by going on a staycation at the one and only, luxurious SoHo Hotel?

With exquisitely comfortable rooms and furnishings, top-rated amenities and services, and of course, stunning views of the CN Tower, SoHo is the perfect spot to retreat with your love and spend quality one-on-one time enjoying each others company.

Plus, if you end up deciding to leave the hotel for a bit of exploring, the SoHo Hotel is located in the heart of Toronto’s Entertainment District and is just steps away from some of the city’s hottest bars, restaurants, and attractions.

If you’re looking to take a trip this winter season with your romantic partner, look no further than the exciting and bustling city of Toronto. Because, whether you’re looking for fun, romance, or adventure, this incredible city truly does have it all.