Howl’oween at The Bentway 2026: Free Dog Costume Contest, Prizes & Halloween Fun
Howl’oween returns to The Bentway October 24, 2026! Enjoy free admission, dog costume contests, prizes and a pet market from 12–4 p.m.
Original WTFToronto promotional illustration; not a photograph of the actual event.
Howl’oween at The Bentway 2026 at a glance
October 24, 2026 · 12–4 PM · The Bentway Skate Trail · 250 Fort York Boulevard
The Bentway’s free Howl’oween runs October 24 from noon–4 p.m. at the Skate Trail. Contest check-in is noon–12:45 p.m., the pack walk begins at 1 p.m., prizes are for selected winners, and Yappy Hour runs 3–4 p.m.
What's actually free?
Event admission
Spectating
Paid or optional
Toronto Dog Moms Market purchases; refreshments are not confirmed complimentary
Limited or conditional
Do not promise attendee giveaways, free market products or refreshments, free parking, guaranteed contest registration, or prizes for every contestant.
Categories are Best DIY Costume, Best Family Costume, Best Pet Superhero Costume and Judges’ Picks. Advance registration is encouraged; check Eventbrite for current availability. Ren’s Pets and Kidde provide prizes for selected winners. The Best Pet Superhero Costume prize is valued at $500; do not imply that every Ren’s Pets category has the same value or that attendees receive free gifts.
Market and refreshments
Toronto Dog Moms Market features local pet-focused vendors. Purchases are extra. Music and seasonal refreshments are mentioned, but complimentary food and drinks are not confirmed.
Access and dog safety
Dogs must remain leashed and should be comfortable around crowds and other dogs. Visitors without dogs are welcome. Youth prize recipients must have an adult aged 19 or older accompany them and accept prizes. Accessible washrooms are available noon–4 p.m. The outdoor event is planned rain or shine, subject to severe-weather cancellation.
Getting there
The Bentway Skate Trail is beneath the Gardiner Expressway at 250 Fort York Boulevard, not The Bentway Studio or Strachan Gate. TTC access includes the 511 Bathurst streetcar on Fort York Boulevard and the 509 Harbourfront streetcar on Fleet Street. Paid Green P parking is available nearby; parking is not free.
Frequently asked questions
Is Howl’oween at The Bentway free?
Yes. Admission is free and donations are optional. Market purchases and refreshments may cost extra.
When and where is the event?
Saturday, October 24, 2026, from noon to 4 p.m. at The Bentway Skate Trail, 250 Fort York Boulevard, beneath the Gardiner Expressway.
Do you need to register?
Advance registration is encouraged for costume contest participants. Spectators do not need to enter. Check Eventbrite for current contest registration availability.
What time does the costume contest start?
Contest check-in is noon–12:45 p.m. at the yellow Info Tent. The costume pack walk begins at 1 p.m.
What are the costume categories?
Best DIY Costume, Best Family Costume, Best Pet Superhero Costume and Judges’ Picks.
Are there prizes?
Ren’s Pets and Kidde provide prizes for selected contest winners. Prizes are not gifts for all attendees.
Can children attend?
Yes. Youth are welcome. Contestants under 19 must be accompanied by a caregiver aged 19 or older to qualify for and accept a prize.
Can I attend without a dog?
Yes. Spectators and visitors without dogs are welcome. Dogs must remain leashed.
Will the event happen if it rains?
The event is planned rain or shine, but severe weather may cause cancellation.
Howl’oween returns to The Bentway Skate Trail on Saturday, October 24, 2026, from noon to 4 p.m. The free, dog-friendly Halloween event takes place beneath the Gardiner Expressway at 250 Fort York Boulevard. Optional donations support The Bentway’s programming; they are not an admission fee. Spectators are welcome, whether or not they bring a dog or enter the contest.
Event schedule
12–12:45 p.m.: Costume contest check-in at the yellow Info Tent
12:45 p.m.: Opening remarks
1–1:30 p.m.: Costume contest pack walk
1:45–2:30 p.m.: Judges’ deliberations by category
2:30–2:45 p.m.: Prize ceremony
3–4 p.m.: Yappy Hour
Advance registration is encouraged for contest participants. Check the official Eventbrite page for current registration availability; do not assume registration guarantees a place or that late arrivals can join.
Costume contest categories and prizes
The four categories are Best DIY Costume, Best Family Costume, Best Pet Superhero Costume and Judges’ Picks. The new Best Pet Superhero Costume category is supported by Kidde and has a prize valued at $500. Ren’s Pets provides prizes for Best DIY Costume, Best Family Costume and Judges’ Picks. The organizer references $500 in connection with Ren’s Pets prizes but does not establish whether that is a total value or applies to each category. Prizes go to selected winners only; they are not gifts for all attendees.
The contest is hosted by Ella Mayo, with guest judges including Zeppi the Pom. Toronto Dog Moms Market features local pet vendors offering products such as treats, accessories and grooming goods; purchases cost extra. Music and seasonal refreshments are planned, but complimentary food or drinks are not confirmed.
Dogs must remain leashed and should be comfortable around crowds and other dogs. Youth participants must be accompanied by an adult aged 19 or older to qualify for and accept a contest prize. The outdoor event is planned rain or shine, but severe weather may force cancellation.
The Skate Trail has flat paved and wooden-decked surfaces accessible to mobility devices, and accessible washrooms are available from noon to 4 p.m. Contact The Bentway about additional access needs. Paid Green P parking is available near 250 Fort York Boulevard and 800 Fleet Street; parking is not free. TTC access includes the 511 Bathurst streetcar on Fort York Boulevard and the 509 Harbourfront streetcar on Fleet Street; check service advisories before travelling.
Find it under: EVENTS · Halloween Events · Free Experiences · Events · Dog-Friendly · Fort York · CityPlace · October 2026
Official sources and Toronto discovery
The Bentway — Howl’oween 2026 — Event facts and links follow the user-supplied VERIFIED editorial brief. Contest prizes are for selected winners only; do not present them as attendee giveaways.
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