Here is a funny thought. Somewhere in Toronto right now, a dog is being measured for a cape, and that dog has no idea what’s coming. Howl’oween, the city’s reigning fall costume extravaganza for dogs and the humans who dress them, is back at The Bentway on Saturday, October 24 — and this year brings a brand-new way for your pup to compete for glory.
It’s a pay-what-you-choose afternoon, 12 to 4 p.m., under the Gardiner Expressway at The Bentway Skate Trail. You do not need a costume. You do not, technically, need a dog. You just need an appreciation for the spectacle of a chihuahua in a pumpkin suit.
What’s Actually Going On Here
At its core, Howl’oween is a costume contest with the production values of a real fashion show — runway included — wrapped around an afternoon of live music, local pet vendors, seasonal treats, and warm drinks for anyone whose paws aren’t involved in the competition.
“Howl’oween is one of those events that really captures the creativity and sense of community we love seeing at The Bentway,” said Alex Rand, Creative Producer, Major Projects at The Bentway. “Every year, people surprise us with how much imagination they bring to the costume contest, and we can’t wait to see Toronto’s dogs take over the runway this year.”
Translation: come prepared to see things you didn’t know a dog costume could be.
Your Host and Her Panel of Experts
Running the show is Toronto drag royalty Ella Mayo, back for another year of hosting duties and emceeing the costume contest with the kind of flair this event deserves. Backing her up is a judging panel that takes its canine fashion seriously: local dogfluencer Zeppi the Pom, Shana Hillman of CityPlace & Fort York BIA, and Lisa Watson, Senior Market Manager at Ren’s Pets.
Four Categories — And a Brand-New One
This year’s lineup gives dogs four different lanes to compete in: Best DIY Costume, Best Family Costume, Judges’ Picks, and the newest addition, Best Pet Superhero Costume.
Here’s how it works: during the Costume Contest Pack Walk, every pup gets their moment on the Skate Trail runway, and judges pull standout contenders from each category back onstage for a final showdown before crowning the winners. Low-stakes for the humans, extremely high-stakes for the dogs who have been training for this.
The new superhero category comes courtesy of Kidde, joining this year as Lead Pet Safety Partner — and it’s not just a cute theme. It’s tied to a genuinely good message about pet safety at home, built around the fact that dogs have some seriously underrated instincts, and can even be trained to alert their people when smoke or carbon monoxide alarms go off. Turns out your dog really could be a superhero. Might as well dress the part.
The Community Making It Happen
None of this comes together without a pretty dedicated pack of partners. Returning Presenting Pet Partner Ren’s Pets is bringing giveaways and prizes for the four-legged crowd, while Lead Neighbourhood Partner CityPlace Fort York BIA is opening the day up to the whole neighbourhood and shining a light on pet-friendly local businesses worth a visit while you’re in the area.
Beyond the main event, there’s plenty to wander through — pet-focused vendors from the Toronto Dog Moms Market, something warm to drink, a seasonal treat or two, and an entire afternoon dedicated to the simple joy of watching dogs be dogs, dressed as other, more dramatic things.
The Schedule
- 12:00 – 12:45 p.m. — Costume Contest Check-In + Registration
- 12:45 p.m. — Opening Remarks
- 1:00 – 1:30 p.m. — Costume Contest Pack Walk at The Bentway Skate Trail
- 1:45 – 2:30 p.m. — Judges’ Deliberations Onstage
- 2:30 – 2:45 p.m. — Prize Ceremony
- 3:00 – 4:00 p.m. — “Yappy Hour” for neighbourhood pups and their people
Before You Head Down
Rain or shine, the party happens under the Gardiner regardless. Spectating is welcome with or without a dog in tow, but any pups attending need to be comfortable around crowds and other dogs, and leashed the entire time — no exceptions, even for the superheroes.
If your dog is entering the costume contest, pre-registration is encouraged in advance on Eventbrite.
