Enjoy free skating at Nathan Philips Square in downtown Toronto this winter

The Ultimate Toronto Experience for Family and Friends During the Holidays

Published: December 5, 2022

The holidays are a time to welcome friends and family from near and far. This holiday season, treat your visitors to a one-of-a-kind Toronto experience they won’t soon forget. With lots of fun and unique activities in and around the city to wow your guests, we guarantee that even locals will have a blast exploring Toronto this winter.

We love a surprise airport welcome as much as anyone and now you can start your visit with incoming friends and family even earlier. With our Meeter & Greeter fare, guests travelling from Union, Bloor or Weston UP Express stations can purchase a special return ticket at a reduced fare making it an ideal way to pick up guests as they arrive at Pearson International Airport for the holidays.

Outdoor Winter Activities In Toronto

Northern Lights

Photo Courtesy: Northern Lights

Bring your festive spirit to Northern Lights TO at Grand Bizarre, Exhibition Place! Brand new for 2022 and open December 1 until January 8, this massive immersive holiday-themed experience will dazzle visitors of all ages. The outdoor festival starts with a 30-foot light-filled tunnel that transports visitors to an enchanting world of oversized décor, larger-than-life toys, holiday music, and custom-built light installations right in downtown Toronto, easily reached via GO Transit from UP Express Union Station. Fun for the whole family this winter, enjoy a wide selection of festive food and drinks including wine and holiday spirits, have a visit with Santa or the Grinch, stroll through the Christmas tree forest and explore the vendor market and holiday-themed games with plenty of photo opportunities. Plus, Metrolinx has partnered with Northern Lights TO and as a PRESTO perk, cardholders can save 20% off admission with promo code PRESTO20 (applicable for ticket admission for all dates excluding Saturdays). A portion of every Northern Lights TO ticket sold will be donated to the Sick Kids Foundation.

Enjoy free skating at Nathan Philips Square in downtown Toronto this winter

Bundle up and walk through a winter wonderland of trails in High Park, near UP Express Bloor Station, or try tobogganing at Riverdale Park East. Rent a pair of skates or lace up your own with your visitors and hit the ice at Harbourfront Centre, Nathan Phillips Square or on the outdoor trails along The Bentway and Colonel Samuel Smith Park.

Looking for more places to hit the ice? Check out some more of Toronto’s free outdoor ice rinks so you can get your skate on!

If outdoor activities aren’t on your to-do list, invite your visitors to chill out at one of Toronto’s many spas or indulge in a staycation right in the heart of downtown.

Toronto’s Christmas And Holiday Markets

The Distillery District

Photo Courtesy: The Distillery District

Now that family and friends have arrived for the holidays, it’s time to get outside and enjoy a Canadian winter at one of the city’s outdoor Christmas and holiday markets.

The Holiday Fair In The Square returns to Nathan Philips Square, with ice skating, one-of-a-kind shopping from local vendors, rides, games, and more for the whole family. An easy walk from UP Express Union Station, for a more grown-up experience, enjoy a festive evening with drinks at the Polar Point Bar and tasty treats at this bustling winter carnival.

Holiday Hills festival

Photo Courtesy: Stackt

Until December 31, STACKT Market’s free Holiday Hills festival brings the holiday spirit to Bathurst Street, located a 20-minute walk or short TTC streetcar ride from UP Express Union Station. Featuring live music on Fridays, a ferris wheel, immersive photo experience, take in the outdoor festive ambiance with some holiday shopping, community-led events, workshops and family programs all month long.

Elsewhere in the city, explore the Bloor-Yorkville Holiday Magic festival of lights, stroll through the Distillery District’s annual Christmas Market and Winter Light Festival with a cup of hot chocolate from SOMA Chocolate, or head to the Toronto Zoo via GO Transit for the spectacular Terra Lumina light displays during the winter months. North of downtown near UP Express Pearson Station, you’ll find Christmas Glow at the Toronto Congress Building for some holiday shopping to find that gift for someone special – or yourself!

Explore Toronto’s Top Attractions And Events

The underwater viewing tunnel at Ripley’s Aquarium of Canada is a must-see for Toronto visitors

Photo Courtesy: Ripley’s Aquarium of Canada

Toronto’s iconic landmark, the CN Tower, will be on the top of the list of things to do for first-time visitors for panoramic views of the city and Lake Ontario. Meanwhile, the young – and young at heart – will be delighted with North America’s largest underwater viewing tunnel at Ripley’s Aquarium of Canada, conveniently connected via the indoor Skywalk from UP Express Union Station.
Escape the cold with a day at the museum! Some of Canada’s most-prestigious art galleries and museums are right here in Toronto. You and your guests can lose track of time in the Royal Ontario Museum, the Art Gallery of Ontario, and the Bata Shoe Museum, among many others.

See some live music and performing arts at Toronto’s iconic performance venues like Massey Hall

Photo Courtesy: Massey Hall/Jag Photography

As Canada’s capital music city, there’s always something happening at one of Toronto’s many concert halls and performance spaces. Check out the listings for landmark concert venue Massey Hall, treat your guests to an afternoon of live jazz at The Rex, or experience Handel’s Messiah by the Toronto Symphony Orchestra, all just minutes from UP Express Union Station.
Plus, this year the National Ballet of Canada continues its annual staging of The Nutcracker which has been drawing sold-out crowds for nearly three decades and remains one of the city’s top holiday events for families.
Looking for even more ideas? We’ve got you covered with 10 reasons to get dressed up and have fun in Toronto.

Eat, Drink, And Be Merry

Toronto is a food-lover’s paradise now listed in the Michelin Guide to the world’s best restaurants

Toronto is a food-lover’s paradise! With cuisines from around the world there are endless options for every taste and budget – and more than 7,500 restaurants and bars ready and waiting for you. Just a short walk from UP Express Union Station, spend an afternoon eating your way around Toronto’s famed St. Lawrence Market or sign up for one of the market’s popular cooking classes this winter. Take a culinary stroll with family through one of the city’s many cultural neighbourhoods like the Greek village of The Danforth, Little Jamaica, the Polish hub of Roncesvalles near UP Express Bloor Station, the Gerrard India Bazaar, or check out one of Toronto’s two Chinatowns.
Impress the foodies in your life with a memorable Toronto dining experience. The Michelin Guide recently honoured 13 Toronto eateries including Alo, Alobar Yorkville, Quetzal, and Osteria Giulia with one Michelin star while Yorkville’s Sushi Masaki Saito received two stars. The Michelin Guide also recognized more than 60 restaurants including ones that won’t break the bank. From Chinatown’s Mother’s Dumplings and Indian Street Food Company’s tasty snacks to Kensington Market wine bar Grey Gardens and Cherry Street BBQ, this is one city you won’t go hungry in.

Enjoy Toronto’s Food And Drink At Home

Toronto take-out options for holiday gatherings include Levant Pizza

Photo Courtesy: Levant Pizza

For entertaining at home, bring the city’s best to you! Showcase Toronto’s top-notch food and drinks with a selection of beers from one of our many local craft breweries near UP Express Weston Station or make it a cocktail night with the locally-made Slurp cocktail mixes and spirits from Laneway Distillers or Spirit of York. If it’s been a while since your friends and family have been able to visit Toronto, why not try something new? Check out one of the top new restaurants to open during the pandemic including Bar Pompette, Little Sister Portland, and Levant Pizza, many of which offer takeout and delivery.

Toronto For The Sports Fan

Events to check out this winter include Toronto Maple Leafs and Toronto Marlies hockey games

There’s nothing more Canadian than a hockey game so grab tickets for you and your guests to see hometown heroes the Toronto Maple Leafs or check out the Toronto Marlies on their home turf, easily accessible from UP Express Union Station via GO Transit. If a game isn’t in the cards, bring your hockey-lover to the Hockey Hall of Fame, right outside UP Express Union Station, and get a picture with the Stanley Cup.
Toronto is more than a hockey town, we’re also home to Canada’s only NBA team, the Toronto Raptors. Be sure to check the game schedule to see this NBA Championship-winning team on the court at Scotiabank Arena, adjacent to UP Express Union Station. With convenient and spacious luggage racks and overhead storage on board every UP Express train, you won’t have to worry about finding room for your sports memorabilia and shopping purchases when it’s time to head home.

Go Beyond Toronto

Canada’s Wonderland transforms into WinterFest this holiday season

Not only can UP Express help visitors get from Pearson Airport to downtown Toronto in 25-minutes, it can also be the start of your journey when it comes to exploring winter activities outside of the city. With complimentary Wi-Fi on board UP Express, you can plan your trip to Niagara Falls by connecting via GO Transit at UP Express Union Station. While Niagara Falls may attract millions of visitors in the summer, it’s a totally new experience to see the thundering falls ensconced in a layer of ice and snow.
An easy day trip from Toronto, be sure to check out the annual Winter Festival of Lights light displays around the falls or head to picturesque Niagara-On-The-Lake for a day of shopping and dining along the town’s historic main street. Less than a 10-minute walk from the Niagara Falls GO Train Station, downtown Niagara Falls comes alive with a Christmas market on Fridays, Saturdays, and Sundays until December 18 making it the perfect place for some last minute shopping and snacks before heading back to Toronto.
Closer to Toronto, this year Canada’s Wonderland transforms with WinterFest, an immersive holiday experience for the whole family. The one-of-a-kind winter event features ice skating, live shows and holiday entertainment, festive food and seasonal merchandise under millions of spectacular lights.

The Ultimate Toronto Experience Awaits

Toronto comes alive in the winter months, offering a one-of-a-kind city experience. No matter where your friends and family are visiting from this holiday season, UP Express can help visitors easily reach their destinations with frequent and convenient service between Pearson Airport and downtown Toronto, seven days a week.