Dog-Friendly Toronto Holiday Events to Explore This Season 🎄🐾

The holiday season in Toronto isn’t just for humans — our four-legged friends deserve to get in on the fun too! Whether you’re sipping cocoa under twinkling lights or strolling through festive markets, there are plenty of dog-friendly Toronto holiday events where your pup is welcome to join the cheer. At Happy Go Lucky Pet Club, we’ve rounded up four of our favourite places to bring your dog this winter. Grab your leash, bundle up, and get ready for some tail-wagging adventures!

1. Holiday Hills at Stackt Market

Where: 28 Bathurst St, Toronto When: November 14 - December 28th 2025

Time: 12pm-10pm (Tuesday - Sunday. Closed Mondays)

Tickets: FREE

The Holiday Hills festival at Stackt Market transforms this west-end hub into a cozy winter wonderland. Expect outdoor vendor huts, glowing art installations, food trucks, and live entertainment. Best of all — Stackt Market is dog-friendly year-round, so your pup can explore the holiday festivities right by your side.

🦴 Pro tip: Stop by Belgian Moon Brewery’s patio for a warm drink while your dog lounges by the fire pits.

2. The Distillery Winter Village

Where: The Distillery District, 55 Mill St, Toronto When: December - Jan 4th 2026

Time: 10:00 a.m. to 9:00 p.m. Sunday–Thursday and 10:00 a.m. to 10:00 p.m. Friday–Saturday

Tickets: Tickets are required for peak times, including: Opening Night; Fridays, Saturdays and Sundays after 4:00 p.m.; Thursdays in December after 4:00 p.m.; and daily from December 15 - 31. All other times, entry is free.

One of Toronto’s most magical holiday destinations, the Distillery Winter Village is picture-perfect for a festive dog walk. Wander the cobblestone streets lined with sparkling lights and artisan vendors, and don’t forget to snap a photo of your pup by the giant Christmas tree. While indoor shops and dining areas may have pet restrictions, the outdoor areas are dog-friendly, making this a must-visit holiday stop for you and your furry friend.

🦴 Pro tip: Visit early in the day or on weekday mornings for a quieter, more relaxed stroll with your dog.

3. The Well Holiday Market

Where: 486 Front St W, Toronto When: Wednesday to Sunday until December 28 2025

Time: Wednesday to Friday: 4:00 pm-8:00 pm Saturday: 12:00 pm-8:00 pm Sunday: 12:00 pm-6:00 pm

Tickets: FREE

New to the city’s festive lineup, The Well Holiday Market brings holiday charm to one of Toronto’s trendiest mixed-use spaces. You’ll find seasonal vendors, twinkling lights, and cheerful photo ops — all in a modern, open-air setting that’s perfect for pups. The Well is dog-friendly throughout its outdoor common areas, so your furry friend can join you as you shop and snack your way through the market.

🦴 Pro tip: Keep an eye out for pop-up pet-friendly events and photo booths — a few vendors have been known to offer dog treats too!

4. WinterFest at Harbourfront Centre

Where: 235 Queens Quay W, Toronto When: Nov 28 - Dec 31 2205

Time: Fridays: 6pm-11pm, Saturdays: 12pm-11pm, Sundays: 12pm-8pm

Tickets: FREE ENTRY

If you and your pup love being by the water, WinterFest at Harbourfront Centre is the perfect seasonal outing. Take a delightful stroll down Winter Feast Lane and wander through a lit pathway of trees while exploring festive food vendors offering holiday-themed savoury bites and sweet treats. While the indoor spaces are for humans only, the outdoor areas (including the skating rink viewing zones and vendor village) are dog-friendly, making this a great stop for festive photo ops with Toronto’s skyline in the background.

🦴 Pro tip: Wrap your pup in a cozy sweater — the lake breeze can get chilly!

Celebrate the Holidays with Dog-friendly Toronto festivities!

Toronto truly shines in winter, and thanks to so many dog-friendly holiday events, you don’t have to leave your furry friend at home to enjoy the magic. Whether you’re visiting Holiday Hills, the Distillery Winter Village, The Well Holiday Market, or WinterFest at Harbourfront, there’s something special for every pup (and their human).

From all of us at Happy Go Lucky Pet Club, we wish you and your four-legged family members a joyful, paw-some holiday season! 🎅🐶