Toronto’s Top Trick-or-Treating Streets: Where to Haunt for the Best Halloween Loot

Halloween is almost here, and it’s time to dust off those costumes and prep for the ultimate candy hunt! Whether you’re a seasoned trick-or-treater or just chaperoning the kids, knowing where to go can make all the difference between a sweet haul and a night full of “fun-sized” disappointments. Fear not (or maybe do; it is Halloween, after all) because we’ve rounded up the most legendary streets in Toronto for scoring big on candy. Grab your broomsticks, pillowcases, and flashlights—it’s time to map out your trick-or-treating adventure!

1. Glendonwynne Road (High Park North)

If you're after the perfect Halloween street with all the spooky trimmings, Glendonwynne Road is your go-to. This quiet residential street near High Park transforms into a Halloween wonderland, with homes showcasing eerie decorations and plenty of treats. Word has it: the residents here go all out, so expect to see giant spiders, elaborate haunted house setups, and maybe even a few fog machines. Just try not to get distracted by the decorations—you’ve got candy to collect!

2. Hanna Road (Leaside)

Looking for a trick-or-treat spot that’s kid-friendly and candy-heavy? Hanna Road in Leaside checks all the boxes. This street is known for its family-oriented vibe, and come Halloween, it’s like walking into a neighborhood-wide party. The houses are decked out in fun (sometimes freaky) decor, and the treats are plentiful. It’s a hotspot for little ghouls and goblins, so you’ll have plenty of company as you race from door to door, scoring candy like it’s your full-time job.

3. Bain Avenue (Riverdale)

Bain Avenue in Riverdale is famous for its community spirit—and when Halloween rolls around, it’s like stepping into a Halloween carnival. The street is lined with century homes that embrace the spooky season in a big way, often competing for the best-decorated house. Some homes even create mini-haunted walkways, so prepare for a few jump scares between candy pickups! The trick-or-treaters here are known to leave with heavy bags and big smiles.

4. Woodfield Road (Leslieville)

Nestled in Leslieville, Woodfield Road is a hidden gem for trick-or-treaters. It’s off the main drag, but those who know about it come yearly for the unbeatable Halloween experience. The residents on this street love getting into the Halloween spirit, with everything from ghostly figures in windows to animatronic zombies on lawns. The vibe is welcoming and fun, and rumour has it a few houses give out the coveted full-size candy bars. Pro tip: Get there early!

5. Wychwood Park (Wychwood)

For a magical Halloween experience, Wychwood Park feels like you’re stepping into a mystical forest—except with more jack-o'-lanterns and candy. This historic enclave has the perfect mix of eerie charm, with its large, old homes and lush greenery setting the mood for a spooky night. The street winds through the park, giving it an almost storybook-like quality, and the houses here don’t disappoint when it comes to festive decorations. You may feel like you're trick-or-treating in a haunted mansion movie set, but don’t worry—the only thing you’ll find behind these doors is candy!

Each of these streets is known for pulling out all the stops on Halloween night. So, whether you’re seeking jaw-dropping decorations, a chance for full-size chocolate bars, or just a solid trick-or-treating experience, these spots will surely make your Halloween one to remember!