Howl’oween at The Bentway Returns October 24 With a Dog Costume Parade
Toronto’s dogs have a Halloween event of their own this weekend. Howl’oween returns to The Bentway on Saturday, October 24, 2026, with a costume contest, local pet vendors and an afternoon of activities beneath the Gardiner Expressway.
The main attraction is the Costume Contest Pack Walk, when dressed-up dogs take a turn along the Skate Trail. New this year is a superhero-themed award for pets whose outfits belong in a comic book.
Admission is free, with optional donations to The Bentway. You do not need to own a dog, dress up or enter the contest to attend.
Howl’oween 2026: Quick Details
| Date | Saturday, October 24, 2026 |
| Time | 12 p.m. to 4 p.m. |
| Location | The Bentway Skate Trail, 250 Fort York Boulevard, Toronto |
| Admission | Free, with an optional donation |
| Contest registration | Advance sign-up encouraged; contestant check-in is 12–12:45 p.m. |
| Who can attend | Dog owners, families and spectators without dogs |
A New Superhero Category Joins the Dog Costume Contest
Entrants can compete in four categories: Best DIY Costume, Best Family Costume, Judges’ Picks and Best Pet Superhero Costume. The superhero category makes its debut in 2026 with support from Kidde, the event’s lead pet safety partner.
A homemade outfit could be a fit for DIY, while coordinated looks between people and their dogs may suit the family category. Judges will call back standout contestants for a final onstage look after the pack walk.
Toronto drag performer Ella Mayo returns as host. The guest judges include local dogfluencer Zeppi the Pom, Shana Hillman from CityPlace & Fort York BIA, and Lisa Watson of Ren’s Pets.
Ren’s Pets is backing prizes for the DIY, family and judges’ categories, while Kidde is sponsoring the superhero award. Prizes go to selected contest winners rather than everyone who attends.
The Full Howl’oween Event Schedule
| 12–12:45 p.m. | Contest check-in and registration at the yellow Info Tent |
| 12:45 p.m. | Opening remarks |
| 1–1:30 p.m. | Costume Contest Pack Walk on the Skate Trail |
| 1:45–2:30 p.m. | Onstage judging and deliberations |
| 2:30–2:45 p.m. | Prize ceremony |
| 3–4 p.m. | Yappy Hour for dogs and their people |
Owners entering their dogs should arrive during the stated check-in window. If you are mainly coming to watch, the parade begins at 1 p.m. The Bentway encourages advance registration through its Eventbrite listing.
Local Pet Vendors, Fall Treats and Yappy Hour
The Toronto Dog Moms Market will bring pet-focused vendors to the event. The Bentway’s listing mentions dog treats, accessories and grooming products, so there will be items to browse beyond the costume runway.
Organizers also plan music, warm drinks and seasonal snacks throughout the afternoon. Food, drinks and market purchases may involve additional costs, even though admission is free.
The schedule ends with Yappy Hour from 3 to 4 p.m., after the contest winners are announced. CityPlace & Fort York BIA is also highlighting pet-friendly businesses around the neighbourhood.
What to Know Before Bringing Your Dog
Bring only dogs that are comfortable around crowds and other animals. Dogs must remain leashed at all times, and owners are responsible for their pets during the event.
Families can attend together. However, contestants younger than 19 must have an adult with them to be eligible for a prize and to accept it. You can also come without a dog and simply watch the parade.
The Bentway plans to proceed rain or shine, though severe weather could force a cancellation. The Bentway advises checking its updates on event day. Accessible washrooms will be available from noon until 4 p.m.
How to Get to The Bentway Skate Trail
Head to 250 Fort York Boulevard beneath the Gardiner Expressway. The Skate Trail is the event location, rather than The Bentway Studio or another site along the corridor.
The Bentway lists the 511 Bathurst streetcar at Fort York Boulevard and the 509 Harbourfront streetcar at Fleet Street as transit options. Paid Green P parking is available near 250 Fort York Boulevard and 800 Fleet Street.
If your dog is joining the costume contest, check registration before leaving home. For last-minute schedule or weather changes, refer to The Bentway’s official event page.
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