One of the city’s most adorable Halloween traditions is returning this fall!
Howl’oween is coming back to The Bentway on Saturday, October 24, featuring an afternoon filled with fun and creative canine costumes, local pet vendors, and plenty of seasonal fun beneath the Gardiner Expressway.

From a cute doggy runway walk to warm drinks and seasonal treats, you’ll get to wander through an array of pet-focused stalls from the Toronto Dog Moms Market, enjoy live entertainment, and celebrate the season alongside Toronto’s dog-loving community.
For the very first time, this year’s festivities are introducing a Best Pet Superhero Costume category. Presented by Lead Pet Safety Partner Kidde, the brand-new contest invites local pups to dress up as their favourite cape-crusading icons or invent their own superhero personas for a chance to take home a grand $500 cash prize.
Contestants can also strut their stuff across three other categories: Best DIY Costume, Best Family Costume, and Judges’ Picks, with prize packs valued at $500 courtesy of Ren’s Pets. The event will be hosted by Toronto drag princess Ella Mayo, alongside a guest panel featuring local dogfluencer Zeppi the Pom, Shana Hillman of CityPlace Fort York BIA, and a representative from Ren’s Pets.

The pay-what-you-choose event runs from 12 p.m. to 4 p.m. at The Bentway Skate Trail. Registrations for the costume contest kick off at 12 p.m., followed by the Pack Walk at 1 p.m., deliberations at 1:45 p.m., and the prize ceremony at 2:30 p.m. Afterwards, stick around for a “Yappy Hour” from 3 p.m. to 4 p.m. to mingle with neighbouring pups and their owners.
Whether you’re entering a costumed canine or just stopping by to admire the parade of superdogs, everyone is welcome to join in on the fun rain or shine.
You can find out more details and pre-register your pup in advance here on their website.