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 date ideas in Toronto to enjoy this special season together, from whimsical winter fairs to dreamy candlelit concerts and much more.

Here are 10 romantic dates you have to try this holiday season in Toronto.

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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 18th to December 31st, 2022 (Select nights)

Take a Christmas-themed train ride

If you’re ready to dive head-first into all things festive, you can board one of the many holiday train rides near Toronto this November and December. York-Durham Heritage Railway has filled its schedule with all kinds of Christmas-themed train rides. Among the most popular ones is The North Pole Light UP Express, which runs on several dates throughout the holiday season. The night begins with a Christmas tree lighting, followed by chocolate milk and cookies on board with Mrs. Claus and Santa’s helpers as you journey to the North Pole. Plus, you get to dress in your PJs!

Where: 19 Railway Street, Uxbridge
When: November 25th to December 24th, 2022 (select dates)

Hit up a festive pop-up bar

Toronto’s iconic Christmas pop-up bars, are opening back up for the holiday season. From our favourite local bars to annual holiday pop-ups, there are five festive experiences that are now open in Toronto. And rest assured they’re decked out with Christmas decor.

When: Until the end of the holiday season


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Wander in Distillery’s Winter Village

This year’s Distillery Winter Village title sponsor is Parfums Christian Dior, who designed this year’s centrepiece tree and it promises to dazzle! The tree features 400 custom midnight blue ornaments, 1,700 shiny and matte gold balls, 70,000 twinkling lights, and 1,000 custom Dior star charms. Expect to snack on delicious holiday treats and drinks, and shop for last minute gifts. The Village will remain open until December 31st. Free entry to the village is available on weekdays and during the day on weekends from November 18th to December 23rd. However, tickets are required on weekend evenings.

Where: Trinity Square in The Distillery District
When: Until December 31st

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: Until Friday, December 23, 2022 

Go to the Nutcracker ballet

The National Ballet of Canada has one of the finest versions of the in James Kudelka’s staging from 1995, which opens at a Christmas Eve party in rural 19th century Russia, according to NBC. 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, 2022 to December 31st, 2022


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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: December 1st, 2022 to January 8th, 2023

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: The Metropolitan Community Church of Toronto – 115 Simpson Ave
When: December 20th, 2022, and 21st, 2022 at 6:30 PM and 8:45 PM

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