The most festive things to do in Toronto for a magical holiday season
Candy canes, ice skating and mugs of hot chocolate bursting with fluffy marshmallows — the holiday season has arrived in Toronto.So, get out your tuques and get ready to deck the halls. The city has transformed into a winter wonderland filled with festivities.Here are some of the best holiday happenings taking place in and around Toronto this season.
Toronto Botanical Garden Holiday MarketThis annual market is returning in November with its eco-minded, nature-inspired, relaxed shopping experience.
Find your next planet-friendly, botanically inspired treasure from one of the more than 60 vendors, and don’t forget to grab a bite from the food trucks.Dates Nov. 28 to 30
Address 777 Lawrence Ave. E.
One of a Kind Winter ShowThe 50th One of a Kind Winter Show is the place to go if you’re trying to achieve the ultimate gift-giver status this year.The market, filled with a curated section of holiday goods, will be around for 11 days this season. And don’t forget to stick around for the candy cane competition.Dates Nov. 27 to Dec. 7Address Enercare Centre, Exhibition Place, #1, 100 Princes’ Blvd.
Toronto Art Crawl’s Christmas Pop-UpNow entering its 10th year, this one-day market is bringing over 120 Toronto artists together to offer up all things art, photography, sculptures, jewelry, fashion, home decor, skin care and more.And if that’s not enough, there will also be food vendors and a live set from DJ Kid Artik.Date Dec. 7Address The Great Hall, 1087 Queen St. W.‘The Sound of Music’The holidays are alive with “The Sound of Music.” This smash-hit musical classic is returning to Toronto’s Princess of Wales Theatre, after four successful engagements in the city’s Mirvish theatres dating back to 1964.
Dates Runs until Jan. 4, 2026Address 300 King St. W.Holiday Hills at Stackt MarketHoliday Hills, Stackt Market’s “official kickoff to winter,” will run during the season with winter food and beverages, a curated market, live entertainment, workshops and nostalgic photo ops.Holiday Hills is “designed to be a gathering place in the heart of the city, whether for a casual catch-up, a weekend outing, or a festive tradition in the making,” according to organizers.Dates Runs until Dec. 18
Address 28 Bathurst St.Cavalcade of LightsIf you’re from Toronto, chances are you’ve experienced this annual festival that celebrates illumination throughout the winter. It’s where the official City of Toronto Christmas tree is housed, after all.This year’s program embraces the theme of illumination, cross-cultural celebration and winter activity, highlighting Toronto’s diversity through music, dance, skating, visual arts and site animation.The tree and more than 300,000 energy-efficient LED lights will be illuminated at Nathan Phillips Square from dusk until 11 p.m. each evening during the festival.Dates Opening night celebration on Nov. 29 with select lighting installations and skating until Jan. 7, 2026Address Nathan Phillips Square at 100 Queen St. W.
Christmas at the CastleIt is almost time to experience the magic of the season at Toronto’s beloved castle. Christmas at the Castle will have you wandering through dazzling light displays as you take in the most festive atmosphere in Toronto.There will be stunning seasonal decor, glowing lights, and magical touches around every corner. Get ready to be enchanted this holiday season.Dates Starting Dec. 5, and select nights in DecemberAddress 1 Austin Terr.Geary Winter Block Party
Taking place in one of the world’s coolest neighbourhoods, the Geary Winter Block Party is set to transform 1.2 kilometres of Geary Avenue with local flavours, live tunes, vendors and more over the first weekend of December.“Mark your calendars and get ready to warm up your winter,” the team states.Date Dec. 6Address Geary AvenueDistillery Winter VillageToronto’s Distillery Winter Village has kicked off and there’s no shortage of festive fun on the agenda this holiday season.Now in its 16th year, the celebration has become a global holiday destination and has even been named one of the best Christmas markets in the world in 2025 by CNN.Expect holiday photo ops, outdoor bars, festive food and vendors, the iconic countdown to Christmas clock, the beloved centrepiece tree and more.New this year, Pure Spirit Mews has been transformed into an “elevated dining experience” called Chef’s Lane, with four of Canada’s most celebrated chefs, and four creative takes on festive comfort food.Dates Runs until Jan. 4 and is closed on Christmas DayAddress 55 Mill St.The Westin Harbour CastleThere are plenty of ways to get into the holiday spirit at The Westin Harbour Castle.Throughout the festive season, the waterfront location will offer a wine and wreath workshop, breakfast with Santa, a fondue experience, snow globe making and more.A full list of events, along with booking information, can be found online.Dates Various dates in November and DecemberAddress 1 Harbour SquareWinterfest at Harbourfront CentreToronto’s waterfront is set to transform into a festive holiday destination with twinkling lights, performances, family fun and delicious food.Harbourfront Centre’s Winterfest is returning to the city for the second year in a row after welcoming more than 110,000 visitors in 2024.The celebration will include community skate parties, the Harbourfront Express train ride, festive food, a marketplace and more.Dates Fridays, Saturdays and Sundays from Nov. 28 to Dec. 21Address 235 Queens Quay W.Miracle Toronto Pop-Up Holiday BarToronto’s original Christmas bar is back and bigger than ever with an expansion in 2025. Miracle Toronto has opened two seasonal spots this year to bring its iconic “deck the halls” spirit to the city. The bar has returned to Bloor Street West, along with a new location on the Harbourfront.Expect holiday-themed cocktails, Santa hangouts, snacks like pretzels and sausage rolls and music from DJs.Their popular Drag Brunch will also return every Saturday from 11 a.m. to 2 p.m.Dates Bloor Street West location open until Dec. 19, Harbourfront location open until Dec. 31Address 875 Bloor St. W. at Third Place and 235 Queens Quay W. at Boxcar SocialJava Jingle Pop-Up Holiday BarToronto’s acclaimed Little Sister Indonesian Food Bar has kicked off its popular festive takeover, Java Jingle — a pop-up that has become a “cult favourite” among Toronto’s nightlife crowd for its “extravagant decor and nostalgic holiday energy.”And this year, the takeover has launched with a refreshed Winter Wonderland theme to bring a new look and experience to both of its locations.The pop-up bars will feature 12 festive cocktails, alongside seasonal shots and non-alcoholic options.Dates Runs until Dec. 31Address 102 Portland St. and 2031 Yonge St.BarChef’s Nordic Toronto Pop-Up Holiday BarOne of Canada’s best bars is hosting a Nordic-themed pop-up bar at The Well in Toronto.Known as the city’s “most immersive holiday cocktail bar,” guests are invited to “step into a cosy yurt or bask in the warmth of the fire lounge as you are transported to a world of reimagined cocktails.”Dates Wednesdays to Sundays until Dec. 28Address 486 Front St.
