Toronto at Christmas is arguably one of the best times of year in the Big Smoke! Things have changed since the days of sauntering down to see the Simpsons/Hudson’s Bay windows and scope out holiday scenes, but new traditions have emerged. Regarding Luxury brings you a specially curated, go-to guide of all the hottest events happening around the city into the year-end. Bookmark and share this family-friendly guide to the top Toronto holiday events to round off 2026:
Things to Do: Top Toronto Holiday Events 2026
Distillery Winter Village runs from Nov 12, 2026 to Jan 3, 2027 in Toronto’s historic Distillery District, among the shops and dining establishments. This is Toronto’s signature Christmas market, with an old-world European feel, vendor cabins, food and drink, and a big tree lighting on opening night (12 Nov). Insider tip: weeknights are the calmer time to go.
The Original Santa Claus Parade happens Nov 22, starting 12:30 pm at Christie Pits and finishing near St. Lawrence Market. It’s free, one of the oldest parades of its kind in the world, and it marks the start of the holiday season for many families, with floats, marching bands and Santa at the end.
Cavalcade of Lights is a must see event for Torontonians this holiday season. It kicks off Saturday, Nov 28, 5 to 10 pm at Nathan Phillips Square. It’s free and includes the city tree lighting, live music, fireworks and skating. Last year’s festival ran about five weeks into the new year, so expect the lights and rink to stay up through the holidays.
Fairs, Ballet & Winter Shows
Royal Agricultural Winter Fair will be held Nov 6 to 15 at Exhibition Place. It combines livestock shows, the Royal Horse Show, food and shopping, and it’s a big autumn tradition.
The Nutcracker (National Ballet of Canada) runs from Dec 5 to 31. It’s the city’s top holiday stage production and seats vary widely in price, so book early.
One Of A Kind Winter Show is on Nov 27 to Dec 6 at 100 Princes’ Blvd. This is the main handmade and designer gift market, and each ticket includes free re-entry for the whole run. Often referred to as OOAK, it is a popular trade-show-style event packed with vendors and perfect for shopping for unique Christmas gifts for the whole family.
Casa Loma holiday programming typically runs early December to early January. The historic castle is decorated for Christmas, with Santa’s workshop for kids and evening light displays. It’s ticketed, so check the site for details.
Evergreen Winter Garden (Brick Works) holiday market has it all: food trucks, fire pits and workshops like wreath-making. Every Sunday from November 29 to December 20, the Winter Market brings an extra-special festive energy to the Brick Works that we look forward to all year. Entry to this market is pay-what-you-can.
Holiday Fair in the Square (Sankofa Square) is a nostalgic downtown holiday market at 1 Dundas St E. Holiday Fair in the Square runs December 10 to 20. Admission to the Holiday Fair in the Square is FREE for the whole family.
Kensington Market Winter Solstice / Festival of Lights is held Monday, Dec 21, with a lantern parade and fire show. It’s a local favourite, held annually on December 21st. Admission is Free (donations to Red Pepper Spectacle Arts are welcome). Hand-made solstice lanterns are typically available to purchase on-site for around $30. Assembly begins 6 p.m. at Oxford St. & Augusta Ave & first light happens around 6:30 p.m.
The Toronto Fall Fair, Market and Festival runs Nov. 6 to 8 at Woodbine Park, with free admission, for an early craft market.
Antiques at St. Lawrence Market runs through Dec. 20. Taking place in the St. Lawrence Market North every Sunday from 9:30 a.m.–5 p.m., except the last Sunday of each month, this new weekly market brings together quality antique dealers and unique treasures in the heart of Toronto’s historic market district.
The Swedish Christmas Fair will be held November 21–22, 2026, at the George Brown Waterfront Campus. Enjoy traditional Swedish foods, crafts, folk dancing, and a Lucia festival of light with free admission.
Honorable Mentions: Top Toronto Holiday Events 2026
To round out this extensive list of the best of festive Toronto holiday events, Regarding Luxury has pulled details for other noteworthy get-togethers worth checking out:
Christmas Market by Toronto Art Crawl opens Saturday, November 7, 2026, at The Bentway, featuring 140 handpicked artists, food vendors, and live DJs.
Live at Meridian Hall: Cirque Du Soleil ‘Twas The Night Before Dec 10 – Sat, Jan 2, 2027. This is a holiday acrobatics show: Cirque du Soleil’s amazing holiday spectacular, Twas The Night Before Christmas! You’ll witness their 49th original production and first-ever holiday-themed show.
Christmas By Candlelight is held at Massey Hall Monday, December 21, 2026. The show features West End singers and a live band performing Christmas hits in a candlelight setting.
Candlelight: Christmas Classics & Carols is held at Toronto Old City Hall Fri, Dec 11, 6:30 p.m. CA$49. The Candlelight tribute concert brings the magic of a live, multi-sensory musical experience to awe-inspiring locations like never seen before in Toronto. Hear music of Christmas Classics at Old City Hall under the gentle glow of candlelight.
The Fall Cottage Life Show and Seasons Christmas Show run Nov. 13–15 at the International Centre in Mississauga, showcasing everything from cottage design, renovation and outdoor living to holiday décor, entertaining and Canadian craftsmanship. The Fall Cottage Life Show features more than 200 exhibitors focused on recreational properties and cottage lifestyles, while Seasons Christmas Show highlights festive decorating trends, artisanal gifts and holiday entertaining ideas.
Theresa Longo (B.B.A Hon) is a former Miss Italy World contestant & professional brand ambassador based in Toronto. She covers topics such as performance automobiles, high fashion and world travel. Theresa also has a home in Costa Rica and writes about her experiences there.
