Howl’oween

We’re back with the ulti-mutt fall celebration: Howl’oween at The Bentway! Round up the whole pack, two-legged and four, for our fur-nomenal costume contest. Enjoy prizes, music, local vendors, and cozy fall treats on this tail-wagging afternoon full of laughter, happy howls, and Halloween fun for pups and their people!

It’s the most fetch-ing time of year – Howl’oween returns to The Bentway this October, with our iconic canine costume contest!

Join us for a family fur-endly Saturday afternoon at the Skate Trail filled with the most creative and paw-some costumes, hosted once again by Toronto’s drag princess, Ella Mayo, alongside special guest judges including local legend, Zeppi the Pom. Enjoy puppy prize packs, and an exciting range of pet-focused vendors from Toronto Dog Moms Market. Stay cozy with warm drinks, treats, and celebrate the spooky season in style!

Start planning your costumes and pre-register your pup for an epic strut down The Bentway runway for a chance to win Best DIY Costume, Best Family Costume, and Judges’ Picks categories. New for 2026, we’re launching an exciting additional category – Best Pet Superhero Costume – courtesy of Lead Pet Safety Parter, Kidde! Prizes for the Best DIY Costume, Best Family Costume, and Judges’ Pick Categories are courtesy of Ren’s Pets (valued at $500), and the Best Pet Superhero Costume comes with a cash prize of $500 courtesy of Kidde.

All are welcome to sniff out one of the cutest days of the year for our city’s pups and their people!

What to Expect: 

• Contestants check-in at the yellow Info Tent between 12:00 pm – 12:45pm for further details and instructions.  
• During the Costume Contest pack walk, judges will invite stand-outs from each category onstage for a final round of deliberations and prize winners.    
• All Contestants must either be or be accompanied by a caregiver aged 19+ to be considered for the prizes. Youth are welcome, but an adult is needed to accept the prize.   
• All are welcome to attend, even if you aren’t participating in the Costume Contest or don’t have a dog!    
• All gender and accessible washrooms are available from 12pm – 4pm.    
• This event takes place outdoors, under the Gardiner, rain or shine. 
• Please only bring dogs that are comfortable around crowds and other dogs. Dogs must be leashed at all times.

schedule

12:00pm – 12:45pm: Costume Contest Check-in and Registration

12:45pm: Opening Remarks 

1:00pm – 1:30pm: Costume Contest Pack Walk at the Skate Trail 

1:45pm – 2:30pm: Judges’ Deliberations Onstage per Category 

2:30pm – 2:45pm: Prize Ceremony 

3:00pm – 4:00pm: “Yappy Hour” for our neighbourhood pups and their people!

costume categories

Best DIY Costume

Best Family Costume

Best Pet Superhero Costume

Judges’ Picks

Photos by Mila Bright Zlatanovic