25 Date Ideas for Winter in Toronto

25 Date Ideas for Winter in TorontoKeep it intimate and cozy this winter with some fun dates and things to do during the colder months with a date or your significant other. Get active outside in nature or stay indoors and get your sweat on, indulge in some food and drink, opt for a quintessential classic date like bowling, skating, or try something unique and interactive like an escape room or an art class. This list provides something fun and heartwarming for everyone despite the frosty weather this season.

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1. Enjoy an Enchanted Night Walk at Terra Lumina


Enjoy an immersive experience along a 1.5 km walking path that travels into the future and back. Terra Lumina is the eleventh unique experience created in Moment Factory’s Lumina night walk series.

2. Go skating under the night sky

With several skating destinations and atmospheres to choose from, you and your date will have a field day trying to decide between the brand-new College Park skating trail, the 220-metre Bentway trail under the Gardiner Expressway, the classic Nathan Phillips Square, and more. Don’t forget to consider DJ Skate Nights at the Harbourfront Centre!

3. Have a three-course meal at a Winterlicious restaurant

Choose from over 200 restaurants in Toronto for a scrumptious prix fixe meal ranging from $23/$28/$33 for lunch, and $33/$43/$53 for dinner. Restaurants include Latin American delight, Lena, inside Saks Fifth Avenue, luxurious and modern Japanese spot Miku, and famed vegan joint Planta.

4. Enjoy live music at the Winterfolk Blues & Roots Festival

Enjoy the best of bluegrass, jazz, folk, and blues at this multistage festival hosting over 100 artists and offering musical workshops. Award-winning artists like Abigail Lapell and Jack de Keyzer, mix with inspiring musicians like Lynn Harrison and Clela Errington to encourage attendees to fall in love with new genres.

5. Grab dinner and see a Movie at the TIFF Bell Lightbox

Have dinner at one of the delicious restaurants at the TIFF Bell Lightbox such as Canteen for a friendly selection of sandwiches and salads, or contemporary Luma, for seafood delights and outstanding views of the city. Afterward, catch a new release, an arthouse gem, or a throwback film at the theatre.

6. Go bowling at the Ballroom


Lace up your bowling shoes and opt for a timeless date at a bowling alley. The Ballroom is known as one of Toronto’s most upscale and popular bowling spots in the heart of downtown, where you can play a couple of games, sip on a cold beer, and enjoy pub fare while you’re at it.

7. Go for some friendly competition at the Rec Room

Spend hours roaming this 40,000-square foot space for food, arcade games, VR games, and other entertaining events like karaoke, trivia, ping pong, and club events. Compete, work as a team, or simply enjoy an interactive date at the Rec Room.

8. Attend an art class

Attend an art class with your date at one of many art spaces in Toronto like Pinot’s Palette for an unforgettable night of painting and wine, beer, or cocktails or Paint Cabin for a unique glow in the dark paint party on the last Friday of each month.

9. Head to a Maple Syrup festival

Maple Syrup season is coming up, so what better place to go than a Maple Syrup festival like the Sugar Beach Sugar Shack to huddle up with hot mulled cider, a taste of some maple taffy and sweet treats, and enjoy some live music on a date outdoors.

10. Go for a couples’ spa date

Head on a couples’ spa date and enjoy some rest, relaxation, and pampering through a massage, facial, a soak in the pool, and other body treatments. Choose from beautiful spas like the four-storey Elmwood Spa, the luxurious Four Seasons Spa, or the Turkish-style Hammam Spa.

11. Warm up over cheese fondue

Gather around a warm cheese fondue and eat your heart out over some genuine conversation. Restaurants include BeerBistro for cheese and lager fondue, Carens Rosedale for wine and cheese, and the Bier Markt to dip “everything” pretzels into a piping hot three cheese fondue.

12. Play board games


Opt for hours of classic fun at a board game café, and test your skills and competitive streak at Snakes and Lattes – one of the biggest board game franchises in the city, Mana Pool for games and an interesting selection of international snacks, and Spielhaus for added trivia.

13. Race against the clock at an escape room

Escape rooms can be a great way for you and your date to work together in a fun, race-against-the-clock environment. Solve puzzles, riddles, and work your way through a themed room that can range from murder mysteries to fantasy stories, to adrenaline fueled horror.

14. Head over to an arcade bar

Try your hand at classic arcade machines at an arcade bar, where your childhood and adulthood combine. From Pinball to Pac-Man to Street Fighter, bars like watering hole Get Well, and quintessential Tilt will help you and your date bond over some nostalgia.

15. Go tobogganing at a park

If the weather permits, head to one of the tobogganing hills at a city park for a day of activity. Check out the adventurous options at Christie Pits Park, the relaxed runs at beloved Trinity Bellwoods, or scout out other hidden gems to suit your skill level.

16. Feast your eyes on the Toronto Light Festival in the Distillery District

During a time of year where light is scarce, head out to the Distillery District and indulge in the beautiful light installations that dot the area. Walk through and marvel at this visual adventure, created by several international and local artists for all to enjoy.

17. Drink your way through the Roundhouse Winter Craft Beer Festival

Hosted in the heart of downtown Toronto, sample some of the regions finest brews and complement them with eats from some of the best food trucks in the city in a wonderful winter setting. Additionally, roast marshmallows over the fire, snap a couple of pictures at the photo booth, and enjoy a bunch of fun games like giant Connect Four.

18. Enjoy a night at the ROM After Dark event

Occurring just once or twice a month at the ROM, this rare event is an exciting after-hours event where you can enjoy culture, art, and nature in an experiential evening for food and drink, visual arts, and music. Each event surrounds a certain theme, and there is always plenty to do with a date.

19. Go see some live theatre

Toronto is known as a city for entertainment, and with theatres that have been around for decades, there is no shortage of incredible Broadway shows, musicals, and plays to enjoy. Go and see Phantom of the Opera at the Princess of Wales Theatre, or Hamilton at the Ed Mirvish Theatre or perhaps We Will Rock You, if that’s more your style.

20. Enjoy the tropical plants at the Allan Gardens Conservatory

The Allan Gardens is a true natural gem in the midst of the concrete jungle. This wonderful indoor botanical garden has six greenhouses that house exotic, tropical plants, cacti and succulents, tropical vibes, colorful seasonal plants, and more. Even in the midst of winter, it can feel as if you’re walking hand in hand with your date through a magical patch of nature.

21. Go on an adventurous winter hike


Lace up your winter hiking boots and set out on an outdoor adventure on one of Toronto’s hiking trails. Enjoy a relaxed hike on the Don Valley’s Sun Valley Loops, view some of the natural features along the Scarlett Mills Park Trail, and the incredible vistas and animals at the famous Rouge Valley.

22. Check out some art during DesignTO week

Attend Canada’s leading annual design festival and check out over 100 exhibitions and events in the city’s urban space. Engage with some of the best art installations, intricate jewelry pieces, listen to valuable discussions about design, and even attend the DesignTO Birthday Bash at The Garrison.

23. Go for a cocktail in the city

Try out some winter-specific cocktails and beat the cold at spots like Northwood for a velvety hot chocolate with El Dorado rum and banana mousse, Pretty Ugly Bar for a mouth-watering hot toddy with cognac, or the upscale and infamous The Drake, for boozy apple cider.

24. Get active indoors with some rock climbing or laser tag

Stay warm indoors and get active with some rock climbing or laser tag. Undergo the quintessential laser tag experience at Lazer Maze or action-packed Lazer Quest, or challenge yourself and your date at some of the top rock climbing gyms in the city like the 25,000-square-foot The Rock Oasis or the Toronto Climbing Academy for simulated real-life climbing.

25. Take in Weekend Festivals & Art Installations

25 Date Ideas for Winter in Toronto

Credit: Winter Stations

There are plenty of fun events happening throughout the weekend – from free food events to fantastic music festivals and winter art installations. Take in some of the events this weekend with your date.

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