Toronto’s massive holiday market has returned to downtown

The holidays have set up shop at one of Toronto’s best-known outdoor market spaces.

The Holiday Hills event at STACKT Market has made its triumphant return for the sixth year in a row.

STACKT, known as downtown Toronto’s dynamic open-air market, with a rotating roster of independent pop-up retailers, food vendors and more, has been hosting seasonal events for the bulk of 2025.

Now, with the year coming to a close, this sprawling structure has had its halls thoroughly decked with giant inflatable nutcrackers, a cascading tunnel of lights, wood-burning fires and more.

In keeping with the tradition of promoting both local and renowned vendors, corners of STACKT are serving specialized holiday food, beverages and goods for visitors looking to get their hands on some holiday cheer.

As guests maneuver through the yuletide event — featuring literal chestnuts roasting on open fires — numerous opportunities for local shopping are around every corner, alongside a chance to warm one’s bones with a hot or stiff drink.

[Warm up by the fire. Photo courtesy of STACKT]

In terms of the menu, those popping in will be spoiled for choice, with flagship brands and local talent bringing their A-game.

We managed to swing by Finlandia’s Winter Retreat event, where the vodka maker was slinging drinks heavily inspired by Nordic themes and global winter festivities.

The Northern Light, an elderflower martini with pineapple and rosewater, garnished with a sprig of rosemary, might be the most festive thing you can get in a glass this year that isn’t eggnog.

[Finlandia’s Northernlight]

Those craving something soothing, the ‘Winter Wine Bar’ by Our Story offers not just a great selection of bottles but also fresh, piping-hot mugs of mulled wine. A toasty blend of Our Story’s cabernet and merlot, apple whiskey, and mulling spices (garnished with an orange), this blend is perfect to sit down with at one of STACKT’s numerous firepits throughout its grounds.

For those doing some flash shopping who don’t have time to sit with a drink, Ontario’s own High Noon seltzers are offering cans of their holiday cranberry seltzer, complete with a complimentary festive coozy.

Additional spots for the thirsty traveller to visit include the first-ever Speakeasy Espresso Martini Bar, as well as The Rum Room by Diplomatico, with holiday-themed rum-based cocktails.

Stepping away from the liquid cheer on offer, the Holiday Hills event also features numerous classic vendors and new pop-ups, such as Sundays Pasta Lab, Las Muns’ empanadas, and Mondays Off sliders.

[The Mulled Wine, masterfully brewed by the winemakers at Our Story] 

Youritywithin.com was able to swing by The Cracked Knot, a unique pop-up celebrating its third year at the Holiday Hills event, and inquire about their masterfully crafted wood designs on display.

“I see a lot of moms and dads coming in to visit their kids, who likely live in a condo somewhere downtown, and they get to see what we have, and the reaction from both parents and their kids is always amazing,” Tim Withers, proprietor and owner of The Cracked Knot, told yourcitywithIN.com.

Nearly all of the materials on site at The Cracked Knot are perfected in Withers’ garage out in Burlington. Where, upon completing each piece, be it a table, dining board, or decorative fixture, he takes all of them to STACKT each holiday season, to showcase.

As a result of running his own little Santa’s workshop every year, when the weather gets cold and spirits get merry, Withers has started to get recognized by those working or living in the downtown core.

[Elf on a shelf, at The Cracked Knot] 

“I’ve started to see a lot of repeat customers over the years. I’ve even been up on King Street these past few weeks to grab a coffee before getting ready to open up shop, and I’ve started hearing people shout my name across the street, telling me they’re looking forward to coming by the shop when it opens — you don’t get that kind of thing often in downtown Toronto,” says Withers.

Paired with this immense sense of community, the Holiday Hills event doesn’t stop there, as it also features a Santa Claus Parade, family events, live shows, gingerbread-making and massive outdoor curling stations.

For those looking to take a break from the hustle and bustle of downtown Toronto during the madness of shopping and planning, STACKT’s Holiday Hills event runs from Nov. 14 to Dec. 28.