There’s something so romantic about the holiday season. Maybe it’s the glow of the twinkling lights, maybe it’s the mistletoe, or maybe it’s all the excuses to exchange gifts. Whatever it is, this time of year is all about joy, and having someone special to experience it with is the cherry on top. There are so many ways to enjoy this special season together in Toronto, from whimsical winter fairs to dreamy candlelit concerts and much more.

Here are 13 romantic dates you have to try this holiday season in Toronto.

Explore Wonderland’s WinterFest

Nothing’s more romantic than skating on a frozen lake with the sound of Christmas carols and the glow of twinkling trees all around you. This year’s WinterFest at Canada’s Wonderland is packed with attractions you’re sure to adore, including a starlit tunnel, amusement park rides, and live entertainment. Once you’ve had your fun, you can warm up with some mulled wine and a delicious holiday treat.

Where: Canada’s Wonderland
When: November 13th — December 31st

Take a Santa Express train ride

You’ll want to grab a spot by the window with a cup of hot chocolate for this festive train ride that only leaves the station for a few weeks every year. Get ready to be whisked away to the North Pole in a railway car filled with holiday cheer. In addition to the snowy views and merry decor, the heritage train will have on-board entertainment throughout the journey, including Old Saint Nick himself of course. The train is kept toasty warm, so all you’ll need is a festive sweater.

Where: 19 Railway St
When: Select dates, November 21st — December 18th

Glide on the waterfront ice loop

The Harbourfront Centre’s revamped rink is one of the city’s most picturesque spots for an outdoor skate this season. The rink is nestled along the Lake Ontario shoreline, along with an ice loop in the “south orchard” that connects to the rest of the rink. And once you’re done, you can warm up with a hot drink from Boxcar Social right next door.

Where: Harbourfront Centre, 235 Queens Quay W
When: November 19th, 2021 — March 6, 2022

Hit up a festive pop-up bar

Toronto’s iconic Christmas pop-up bars, Miracle and Sippin’ Santa, are opening back up for the holiday season. Whether you’re in the mood for cheesy over-the-top decor or a holiday bar with a tiki twist, you’ll be able to try both in one night at Bloor St W and Ossington Ave this year. As for the cocktail menu, you can expect professionally-developed creations that combine all your favourite flavours of the holidays.

Where: 875 Bloor St W & 866 Bloor St W
When: November 25th — December 26th

Drive through Snow Magic

Something magical is coming to Ontario Place and it’s like a snow globe come to life! Beginning this November, Snow Magic will invite you to “explore a wonder-filled adventure inspired by fire, ice, and light.” The multi-sensory experience will take you through 3 different worlds — Celestial, Terra Firma, and Oceanic. Your journey will be accompanied by a dreamy “sound story,” which fuses “strings, horns, and synthesizers,” as well as nature sounds. A dreamy way to spend an evening!

Where: 955 Lake Shore Blvd W
When: November 12, 2021 — January 16, 2022

Wander in Distillery’s Winter Village

The Toronto Christmas Market is making a comeback in 2021, but with a new look, feel and name. Now, Toronto will be able to have all of its festive fun at The Distillery Winter Village, a reimagined and rebranded version of the Toronto Christmas Market. The Village is not only a rebrand of the beloved Christmas Market but will also feature a more ‘‘intimate, elevated event.” Sounds like the ideal setting for a romantic date night.

Where: Trinity Square in The Distillery District
When: November 18th — December 31st

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Enjoy the Polar Winter Festival

Toronto’s biggest walkthrough holiday market and festival opens its doors this holiday season and it’s a Christmas fairytale come to life. Not only is it a vendor market with all kinds of treats and gifts to shop for, but it’s also an immersive walkthrough experience with larger-than-life displays, an amusement park with rides, and a destination for all things festive. If you want to add a boozy element to your festival experience, you can hit up the X-Lounge, a cozy cocktail lounge with holiday-themed drinks and fire pits to keep you toasty all night long.

Where: Bandshell Park, 210 Princes’ Blvd
When: November 25th — December 26th

See elves on the Christmas Trail 

Ready for a road trip to the North Pole? Thankfully, you won’t have to travel too far because it’s coming right to you this year! The Canadian Tire Christmas Trail is returning for the holiday season and you’ll see Santa’s village come to life from the warmth of your car. Get greeted by cheerful elves and a tasty treat while you enjoy the festive sights and the event’s holiday season playlist. A date night to remember.

Where: 1000 Murray Ross Pkwy
When: November 13th — December 23rd

Go to the Nutcracker ballet

Toronto is known for having “one of the finest versions” of this magnificent two-act ballet, which premiered in Russia in 1892. The set design, costumes, and orchestra give the whole experience such a magical feel. The show will be taking place at the Four Seasons Centre for the Performing Arts as it does every year. There’s no better way to make the holiday season feel complete in Toronto than this enchanting show.

Where: 145 Queen St W
When: December 10th — December 31st, 2021

Hang out at a festive pop-up patio

Sweaters n’ Snowflakes is a one-stop destination for all things merry and bright right in the downtown core. The outdoor space will be filled with twinkling lights, jolly Santas, and decorated trees, as well as blazing fire pits and heaters to keep you toasty. When you’re not warming up by the fire, you can dig into the mouthwatering woodfire cuisine, sip a variety of festive cocktails, do a wine tasting and paint ugly sweater cookies.

Where: 621 Richmond St
When: December 3rd — 26th & 31st

Experience a real-life Christmas castle 

Casa Loma’s spectacular Holiday Light Tour is one of the city’s most breathtaking sights. Wander through the glowing gardens and tunnels on the property’s grounds, enjoy the live entertainment and prepare to take the most sickeningly cute couple photos on the planet! You can even upgrade your experience to VIP, which includes line bypass, as well as food and beverage credits.

Where: 1 Austin Terrace
When: November 25th — December 30th

Attend a candlelit holiday concert

Nothing’s more romantic than flickering candlelight — add a dreamy live performance inside a stunning church and you’ve got yourself the ultimate setting for quality time with your S/O. The intimate venue is bathed in the glow of candles and the sound of the string quartet playing holiday songs just adds to the special atmosphere.

Where: 115 Simpson Ave
When: Various dates in December 2021

Take a trip to a charming festive town

Christmas in the big city is a beautiful thing, but nothing compares to the charming atmosphere in Ontario’s small towns. The historic buildings, quaint boutiques, and festive decor make this special season one of the best times to visit, not to mention all of the local holiday markets and twinkling light displays you can experience while you’re there. Supporting local has truly never been so fun.

Where: See the best ones here