The holiday season is officially underway, which means you likely have plans (with a capital P) that don’t just involve re-watching all your favourite holiday movies for the thousandth time. While cozying up at home is extremely tempting, the city is full of fun and exciting things to see and do: From festive holiday markets to nostalgic carnival rides, here are 25 fun date ideas to bring a little extra sparkle and joy into your life.
#1 Skate under the stars
Gliding through the ice rink holding your date’s hand under the twinkling lights with music playing in the distance…it’s the stuff of rom-coms. Even if you or your date are skating-averse, it’s a chance to help each other out and cozy up while you’re at it—especially when you’re at one of the city’s top spots for skating.
The Bentway: Every winter, the public space located underneath the Gardiner Expressway transforms into a one-of-a-kind figure-eight skate trail.
Nathan Phillips Square: The skate pavilion is one of the biggest in the city and popular with locals and tourists alike thanks to its central downtown location and view of the CN Tower.
Natrel Rink at Harbourfront Centre: With Lake Ontario and the Toronto Islands shimmering in the background, this pond-turned-skating rink paints a pretty picture.
Union Station: Part of the transport hub’s “Union Holiday” celebrations, this free outdoor ice-skating rink on Front Street is the largest of its kind in the city.
#2 Visit the holiday markets
Toronto’s annual holiday markets are the perfect way to get into the holiday spirit and cross some names off your holiday shopping list. Head to one of the annual markets to sip on some cider, nibble on gingerbread cookies and support local artisans.
Toronto Christmas Market: This Distillery District’s annual market is a Hallmark film come to life. Think twinkling lights and cobblestone streets with the historic site as the backdrop. Treat yourself to freshly baked chimney cakes from Eva’s Original Chimneys or pick up a charming holiday decor. November 14 – December 22
One Of A Kind Show (OOAK): With 800 makers, OOAK is a one-stop shop for unique, handmade crafts and the artisans who make them. It’s the ideal place to pick up presents for the special people in your lives while supporting local businesses. November 21 – December 1
Holiday Fair in the Square: This holiday market meets winter carnival at Nathan Phillips Square has it all. Pick up a present at the Artisan Village, fill up on a delicious snack at one of the food trucks or head over to Jackson Triggs Polar Point for Jackson Triggs’s mulled wine, apple cider and more. December 7 – 23
#3 Share a romantic dinner
There’s no shortage of spots to enjoy a romantic candlelit dinner for two, but these picks will never disappoint.
Bar Isabel: Warm, red lighting, great cocktails and delicious Spanish-inspired shareable dishes make this a go-to date-night spot. Plus, there’s the irresistible dessert selection, which includes the Basque Cake topped with hot sherry cream.
Alo: Housed atop of a Victorian building, Alo is all about thoughtful, refined French dining. If you can snag reservations at this highly coveted hot spot, you’ll see why it’s worth the wait to eat at the restaurant that consistently tops “best of” lists.
Grey Gardens: If you’re spending time in Kensington Market, stop off at Grey Gardens. Grab drinks at the wine bar (there’s a lot of good wine to be had) or be seated for dinner so you can enjoy the soft palm-print mural and brass fixtures while you tuck into some cavatelli.
#4 Sip on some cocktails
Get drinks at one of the city’s hottest bars.
BarChef: Head to this Queen Street West hot spot for an extensive selection of inventive and tasty cocktails.
Bar Raval: Pretend you’re in Barcelona at Bar Raval, which serves up tapas and drinks with a Spanish flair and looks the part, too, with its cool, Antoni Gaudí–inspired interior.
Louix Louis: If you’re feeling fancy, head up to the 31st floor of the St. Regis Hotel. An impressive drinks list aside, the eye-catching ceiling resembles the swirls inside a whiskey glass.
#5 Enjoy Jazz Night at Ripley’s Aquarium
Besides being a family-friendly destination, this aquarium offers activities for everyone. Enjoy live music with your date, along with all your favourite underwater creatures during Jazz Night, held each second Friday of every month.
#6 Watch a holiday classic performed by the National Ballet of Canada
Catch The Nutcracker at the Four Seasons Centre for the Performing Arts, a holiday classic and one of the biggest productions by The National Ballet of Canada with 233 performers. Be prepared to be enchanted by the beautiful costumes, unforgettable performances and a timeless, magical tale.
#7 Spend a magical evening at Casa Loma
The 18th-century castle transforms into a winter wonderland in December and features a flurry of activities. Catch a show by illusionist Professor Wick, watch an ice-skating performance by Glisse On Ice, take a stroll through the lighting display in the estate gardens or wander through the outdoor holiday Christmas market.
#8 Do dinner and a movie at TIFF Bell Lightbox
Upgrade your regular dinner-and-a-movie experience and visit the TIFF Bell Lightbox right in the heart of the city. Film lovers can catch new releases and old favourites and grab dinner at Luma—located on the second floor—which serves up fresh seafood in a cozy setting.
#9 Catch a show at the Soulpepper Theatre
Watch a holiday production at Soulpepper Theatre in the historic Distillery District, Toronto’s largest not-for-profit theatre. This season’s performances include two renowned holiday classics, Peter Pan and A Christmas Carol.
#10 Rediscover Canada’s Wonderland
For the holidays, the amusement park is turning into a different kind of wonderland, brimming with holiday magic at every corner. Think larger-than-life holiday decor in Candy Cane Lane and dazzling light displays honouring Hanukkah, Kwanzaa, Diwali, Christmas and Chinese New Year. Enjoy it as you feast on festive funnel cakes and freshly baked gingerbread cookies.
#11 Tree Lighting Ceremony at Bloor-Yorkville Holiday Magic
Head down to the village of Yorkville Park for the official tree lighting ceremony on Saturday, November 23rd. Hosted by etalk host Danielle Graham, the evening’s festivities include special guest Nefe and a musical performance by Canadian singer-songwriter Ruth B.
#12 Take a night walk at the Toronto Zoo
After nightfall, the Toronto Zoo transforms in Terra Lumina, a 1.5-km walking path that offers an immersive experience and a glimpse into the future. Enjoy the interactive light effects and enter the year 2099, where humans and nature live together in harmony.
#13 Eat your way through St. Lawrence Market
Escape the chill by spending an afternoon inside St. Lawrence Market, the perfect date spot for foodies. Explore the cheese boutiques, bakeries and restaurants together, or even sign up for a cooking class and show off your culinary skills.
#14 Explore art at the AGO
Tour the AGO together, whether you’re an art lover or a newbie. Take in the new Early Rubens and Hito Steyerl: this is the future exhibitions. Before you head out, stop by the shopAGO to take home holiday-themed gifts made by local artists.
#15 Go bowling at the Ballroom
Book a lane, put on your bowling shoes and get ready to bowl at the Ballroom. This expansive bowling alley in the Entertainment District offers hours of uninterrupted fun with snacks to nosh on while you’re at it.
#16 Enjoy a game night at the Rec Room
If you enjoy some friendly competition, make your way to the Rec Room, which offers activities like shuffleboard, ping-pong and pool tables, alongside more than 80 games, including Pac Man and Mario Kart. Rest and recover by grabbing a bite to eat or toast victory with some drinks.
#17 Catch a tree lighting ceremony
The Cavalcade of Lights celebrates its 53rd year, kicking off the holiday season with the lighting of the city’s 60-foot Christmas tree, along with live musical performances, circus arts, a skating party and a dazzling fireworks display.
#18 Head to Ontario Place for the Aurora Winter Festival
Watch Ontario Place, a major park and entertainment venue in the south of Toronto, transform into a magical winter festival. Exciting activities like a 170-foot-long slide in the tube park, an ice-skating pond and amusement rides will make your heart beat just a little bit faster. Plus, you can slow down and enjoy the Christmas market and food gardens.
#19 Enjoy the lights at GLOW
Stroll under a blanket of a million twinkling lights as you walk through the light gardens at GLOW, one of the world’s largest indoor festivals. It’s the perfect way to keep warm and toasty, while having fun with plenty of food and drinks, live music and holiday shopping.
#20 Take a stroll through Allan Gardens Conservatory
The weather outside might be frightful, but the indoor botanical garden is anything but. Featuring six greenhouses, this indoor conservatory shows off a variety of plants and flowers from around the world.
#21 Tap into your artistic side during Paint Night
Tap into your artistic sides at Paint Night at one of Toronto’s many iconic venues, including Ripley’s Aquarium and the Toronto Zoo. Work side by side to create your next masterpiece, or laugh together at your lack of artistic skills. Hey, not everyone’s a Picasso, and that’s okay.
#22 Enjoy the Symphony with TSO
Enjoy an evening of aural delight with the Toronto Symphony Orchestra. Catch Vivaldi’s Four Seasons, TSO’s annual all-Tchaikovsky concert, or TSO Holiday Pops, a holiday concert led by Canadian superstar soprano Measha Brueggergosman.
#23 Laugh together at Second City
If you and your date love to laugh, Second City is the ultimate date-night spot. Catch a show together at one of the most celebrated comedy clubs in the city and find out whether the two of you share the same sense of humour. The Unconventional Holiday Revue is just the thing with its refreshing take on the holiday season.
#24 A night at the (Royal Ontario) Museum
What’s better than a date night at the museum? The ROM offers free admission every third Tuesday of the month during extended hours from 5:30 p.m. to 8:30 p.m. It even transforms into a fun dance party, complete with a live DJ for Friday Night Live at the ROM.
#25 Warm up with some hot chocolate
Hot chocolate makes everything better (and the holidays are the perfect season to say yes to all the extra trimmings like marshmallows, whipped cream and sprinkles). Sweet Jesus serves it three ways—with cake batter, salted dark chocolate or s’mores—while SOMA Chocolatemaker offers a rich and decadent variety, and Bobbette & Belle tops theirs with a toasted homemade marshmallow.