Welcome December! Guess what? Winter in Toronto, Ontario doesn’t mean no dog-friendly fun outside. Just the opposite. Toronto is bursting with outdoor holiday markets, and most are dog-friendly, especially during the days slightly less travelled. However, this is a big city, so we’re talking full and not as full of people and some occasionally, dogs.

And if you bring your dog, you know you’re going to get to meet the other dogs. Or at least that’s true with my overly energetic and friendly spaniel.

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December is also when we make what has become an annual pilgrimage to Hogtown, otherwise known as Toronto, to stay at the very dog-friendly and very centrally located Chelsea Hotel Toronto. The Chelsea is home to the city’s only downtown waterslide (under renovations until January 2026) at one of the hotel’s two pools. (The pools, however, are off limits to pups).

My dog and I once again spent time at the Chelsea Hotel this holiday season, this time venturing a little further than last year (see here). Our destination was the Distillery District’s Winter Village – a place I’d checked out years earlier with my previous dog (see here). But now I’m heading back with an even more energetic pup, hoping to see how this winter festival has expanded in both size and popularity.

But first, we check into the Chelsea Hotel Toronto, one of the largest hotels in the city and very centrally located along Yonge Street. From this dog-friendly hotel, anyone and their dog (literally) can access several of the city’s largest outdoor market festivals listed here. And yes, all these are dog-friendly (on-leash) and standard clean up rules apply.

The Dogtrotting List of Dog-friendly Outdoor Holiday Markets in Toronto, Ontario:

Winter Glow, December 11 to 21, 2025

Winter Glow running December 11 to 21, 2025 has a new home, moved from Nathan Phillips to Square Sankofa Square (formerly Dundas Square) downtown Toronto adjacent to the Eaton Centre. Join about 20 vendors of art, food, toys, and overseas crafts in this central city square, along with food trucks, a carousel, and photos with Santa opportunities.

Distance: Sankofa Square is an easy 5-minute walk about three blocks down Yonge Street from the Chelsea Hotel Toronto.

Winter Market, November 20 to December 22, 2025

Winter Market at the St. Lawrence Market is an outdoor event running Thursdays and Fridays, 11 am to 7 pm; Saturdays and Sundays, 10 am to 7 pm; and Monday, December 22 (the last day), 10 am to 7 pm. In other words, the Winter Market runs Thursdays to Sundays outside the regular St. Lawrence Market, so admission is free. The outdoor holiday market, which includes local gift vendors, entertainment, and food, is pet dog friendly. However, the indoor regular market is not. It is open to service animals only.

Distance: St. Lawrence Market is just shy of 2 km from the Chelsea Hotel Toronto, so it’s about a 20-minute walk through downtown. (If you go that way, you’ll pass Toronto’s famous dog fountain). Considering traffic congestion, walking is frankly the fastest way to get there because public transportation, a cab, or driving will take longer.

Distillery Winter Village, December 8, 2025, to January 4, 2026.

This is the big one in the city: the dog-friendly Distillery Winter Village is an extremely popular European-style outdoor holiday market in Toronto’s Distillery District, December 8, 2025, to January 4, 2026. The event is free admission from 10 am to 4 pm. After 4 pm requires tickets (starting at $15) and often a lineup to get in forms around 3 pm. Note that there’s almost no parking in the area and what’s available is expensive.

Early afternoon is the best time to get there because it’s slightly less busy and Santa, Elves and Carollers can be spotted between 1 and 8 pm. The Distillery Winter Village permits leashed dogs. But it’s busy and crowded so plan accordingly. Weekdays early afternoon are preferable with the pup, and you can still get a photo with Santa (or carollers like I did with my previous dog (here)

Distance: Walking to the Distillery District from the Chelsea Hotel Toronto is possible – it’s a 40 minute to an hour walk, depending on pace (and weather). It’s also possible to take the TTC (Toronto’s city transportation system). It’s easiest to walk to King Street and catch the 504A King Streetcar eastbound and get off at Distillery Loop.

Is the TTC dog-friendly? Yes, but not during ‘peak’ hours 6:30 to 10 am or 3:30 to 7 pm. Leashes are fine. No carriers necessary (unless you prefer it for small dogs). Of course, this excludes service animals. Finally, the Distillery Winter Village has a designated pickup and drop-off spot for taxis and rideshare cars – some willing to take dogs along.

Winterfest at Harbourfront, November 28 to December 31, 2025.

Winterfest at Harbourfront on weekends from November 28 to December 31, 2025, actively promotes itself as a dog-friendly event that permits leashed dogs in all outdoor areas except the skating rink and winter maze. Only service dogs are allowed in the indoor venues. This one is primarily an evening adventure. The winter markets at Winterfest run Fridays from 6 to 11 pm; Saturdays from 4 to 11 pm; and Sundays 4 to 8 pm. Free admission.

Winterfest at Harbourfront features an outdoor market, along with light displays, train rides, and live performances. 2025 marks the second year for this event co-presented with Street Eats Market, so you know they’ll be a broad selection of food trucks – the best way to have dinner with your dog, especially during the winter when patios are closed.

Dog run: Even better, because the Harbourfront area has become a dog destination year-round, a new large, off-leash dog run opened at 50 Queens Quay East, so you can run off some energy before or after visiting Winterfest.

Distance: Harbourfront is about 2.5 km from the Chelsea Hotel Toronto so it’s possible to walk there in about 30- to 40-minutes by heading straight down Bay Street. Or the TTC (see dog-friendly hours above) runs Line 320 bus down Bay Street and takes about 10 minutes.

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Writer bio: Sherri Telenko has been a professional writer for decades and a travel writer for the last two. She’s a member of TMAC (Travel Media Association of Canada) and Dog Writers Association of America and travels almost weekly with her canine companion, Victoria. Contact Sherri at dogtrotting.net here. All written content is original, written by a person, and based on experience and research. Please subscribe!