Toronto's biggest free Halloween party was a beautiful disaster
While Halloween 2024 has officially come and past (so marked by Mariah Carey's annual TikTok proclaiming that Christmas is here), the memories — and bruises — from a night spent at Toronto's biggest Halloween street party will last for a long time to come.
A decades-long tradition that began as a way for the city's 2SLGBTQ+ community to express themselves freely (more on that later), Halloween on Church has blossomed, in a similar way that Pride has, into an annual spectacle experienced by tens of thousands from the city and beyond.
This year, for the first time in my life, I was one of those thousands, and I still don't know how I feel about it.
I love Halloween. Like, really, love it, so sitting on a subway car alongside at least 50 other adults dressed in full costume, I thought I was ready — excited, even, — for what the night would hold.
Surfacing from Wellesley Station and embarking on the two-minute walk to the heart of the event at Church and Wellesley, I trail behind Michael Myers and Leatherface as the sounds of "Monster Mash" pump from the event's performance stage in front of Second Cup. I am in my element.
Almost immediately, I'm greeted by an enormous crowd, decked out in varying levels of costume, milling about the area. Costumed kids and dogs are in attendance, too, while lines of adults snake around the neighbourhood's quintessential watering holes like The Drink, Church Street Garage and Crews and Tangos.
View some of the best costumes at Halloween on Church in this photo gallery.
In the early days, the event took place along Yonge, when spots like the Parkside and St. Charles Taverns would hold Halloween Balls, where, on this one night of the year, folks could dress in drag under the guise of wearing a costume without fear of societal or legal repurcussions.
Quickly, the event equally became an opportunity for people who weren't members of the community to gawk at the spectacle — and, as Church and Wellesley cemented itself as Toronto's gay village, the festivities increasingly concentrated there.
Today, the appeal of the event is less about ogling the 2SLGBTQ+ community (unless you're on the prowl for a new suitor, I suppose,) and more about ogling the people who go well and truly all-out for the holiday — and you don't have to look far to find some.
It quickly dawns on me, as a particularly intricate trio dressed as the Sanderson Sisters from Hocus Pocus breeze by, that drag is still alive and well as the beating heart of the event. Shortly thereafter, they're followed by someone in a rendition of Carol Burnett's iconic curtain dress.
Even when not dressed in drag, though, the event offers an opportunity for many to express themselves creatively.
One duo, dressed as He-Man and She-Ra, tell me that they've been working on their costumes since February, crafting them by hand out of floor mats and an unbelievable amount of hot glue.
"I love Halloween," He-Man tells me with a sheepish grin, adding that he's been coming down to the event since 2017.
Another attendee, a first-year student at TMU wearing a homemade costume depicting the carniverous plant from Little Shop of Horrors tells me that this is their first year attending the event.
"It's our first time downtown for Halloween, so we wanted to check it out," they say, adding that, amid the crowds, their group has been having a hard time sticking together, but nonetheless are "loving it so far."
Some costumes are so elaborate that they require more stationary set ups than the other roaming ghosts and ghouls prowling the street.
One such costume, a twelve-foot tall rendition of Anxiety from Inside Out 2 comprised entirely out of balloons, holds a permanent court between Pocha 1989 and The Cherie, posing with impressed attendees, while across the street, a particularly committed Beetlejuice stands in front of an inflatable sandworm.
By 8:30, I — along with hundreds other attendees who had already had their fill of festivities — was ready to dive for the safety of watching a scary movie on my couch, but quickly found myself unable to move, slowly being crushed between the display window Glad Day Book Shop and a crowd of people 30-deep.
You'd think the Beatles were in town, but that, as it happens, was not the case. Actually, it was Toronto-based Filipinx Drag King, Kreme Inakuchi performing to a Screamo cover of Taylor Swift's "You Belong With Me," that had stopped the flow of traffic altogether.
There's no doubt that Halloween on Church is a great — and important — event for the city, drawing visitors from around the world each year to celebrate not only the holiday, but the city's queer community, too.
Unfortunately, this year at least (a number of attendees inform me that it's "not usually this packed," and that the "great weather" is likely to blame), it ails from poor organization — tens of thousands packed into six city streets with only one main stage to congregate around and a smattering of portapotties.
It's this exact failing that left me sandwiched inside a body crush for at least 45 minutes trying, alongside thousands of others, to leave the event, while an equal number attempted to enter, and, the morning after, I have the bruises to prove it.
Perhaps, being the lover of all things spooky that I am, I'll return to Halloween on Church one day, but, with any hope, it'll expand to anticipate the huge numbers of attendees, becoming even bigger and better than before.
View some of the best costumes at Halloween on Church in this photo gallery.
Fareen Karim
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