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Culture Your City

Pup, set, strut: Howl’oween at The Bentway is back for dogs to compete for best dressed on the dog-way

Dress your dog in their most fetch-ing costume and join Toronto’s paws-itively adorable Halloween celebration, featuring a runway contest, music, treats, and more.

Dogs dressed in Halloween costumes at Howl’oween event with pumpkin decorations and festive atmosphere.
The Bentway welcomes furry friends to compete for best-dressed at Howl-oween! (Courtesy: Mila Bright Zlatanovic/The Bentway, Shane Parent/The Bentway)

What to know

  • The event runs Sunday, Oct. 24, from 12–4 p.m. at The Bentway and features a main costume contest and a full lineup of activities for pups and humans alike.
  • Costume contest registration starts at noon, with prizes up to $500 for categories including Best DIY Costume, Best Family Costume, and Best Pet Superhero Costume.
  • Enjoy a pack walk, live music, local pet vendors, and a “Yappy Hour” for mingling after the contest.
  • Admission is free, but a $10 donation is encouraged; all dogs must be leashed and accompanied by a caregiver aged 19 or older.

Think your dog has what it takes to strut their most fetch-ing fit? Get those doggy capes, tutus, and tiny tiaras out for Howl’oween at The Bentway.

On Oct. 24, hundreds of four-legged friends will have an afternoon of fun from 12-4 p.m., celebrating Halloween at The Bentway for an iconic canine costume contest.

From music, local pet vendors, seasonal treats, prizes, and of course the pup fashion show, there are full of woof-derful activities for owners and pets alike.

Plus, those without pets can still attend and join the paw-some event.

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Toronto drag princess Ella Mayo is hosting the event and will judge contestants alongside local dogfluencer Zeppi the Pom, plus representatives from CityPlace, Forth York BIA, and Ren’s Pets.

How does the Howl’oween costume contest work?

Contestants can compete in four categories:

  • Best DIY costume
  • Best family costume
  • Judges’ picks
  • Best pet superhero costume

“Howl’oween is one of those events that really captures the creativity and sense of community

we love seeing at The Bentway,” Alex Rand, Creative Producer, Major Projects at The Bentway, said in a press release.

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“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,” he added.

What else is happening?

The costume contest is the main event, but there’s more happening throughout the afternoon.

Visitors can browse pet-focused vendors from the Toronto Dog Moms Market, grab warm drinks and seasonal treats, and stick around after the prizes for a neighbourhood “Yappy Hour.” 

The Bentway says dogs should only attend if they are comfortable around crowds and other animals, and they must remain leashed at all times. 

Contestants must also be at least 19 years old or be accompanied by an adult who can accept a prize on their behalf. 

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Howl’oween schedule

12:00–12:45 p.m. — Costume contest check-in and registration
12:45 p.m. — Opening remarks
1:00–1:30 p.m. — Costume Contest Pack Walk
1:45–2:30 p.m. — Judges’ deliberations
2:30–2:45 p.m. — Prize ceremony
3:00–4:00 p.m. — Yappy Hour

The event takes place outdoors under the Gardiner rain or shine. Pre-registration is encouraged for dogs entering the contest, but anyone can attend whether they’re competing, spectating or just there for the costumes.

The Howl’oween event is free — though a $10 donation is recommended.

Grab your free ticket on Eventbrite and see if your dog has what it takes to win the Howl’oween costume contest.

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