TORONTO - Armed with weapons of nap destruction, warriors of all ages gathered at Nathan Phillips Square on the eve of battle.
The featherweight fighters stared each other down on either side of the battlefield, waiting for the cue to charge. On the count of 10, they stormed into the fluffy fray. Pillows arced through the air, connecting with arms, backs and chests.
Such was the scene at the city’s fourth annual pillow fight, organized by Urban Playground Toronto, a group that sets up free events in the city.
Emma Gibson, who has attended all four of the fights, remarked at the absurdity of the event from the sidelines of the battle.
“All these people came here with a pillow and a goal to whack strangers,” she said, looking out over a sea of about 100 participants. “That’s crazy when you think about it.”
But for Gibson, there’s nothing like a good old-fashioned pillow fight to spark those feelings of childlike joy.
“It makes you feel like you’re a little kid and you’re out at the McDonald’s playplace and you just met your new best friend who you’ll never see again,” she said.
That’s the kind of magic Urban Playground founder Kfir Lavi is trying to capture. Alongside the annual pillow fight, Lavi organizes snowball fights, water gun fights and is adding a banana-themed bar crawl to the mix.

He told TorontoToday that founding the organization in 2022 was a bucket list item for him.
“The COVID-19 pandemic left everyone isolated and looking for reasons to bond with one another. I said to myself, ‘Okay, let's look for things that can bring people together,’” he said.
The group’s first event, a snowball fight, failed to draw a crowd. But his follow-up attempt, a pillow fight, found its audience.
“Ever since then, I've been holding activities in the city that generate joy,” he said.
Each year, the pillow fight grows, he said. About 100 people turned out the first year and ballooned to 300 participants last year, according to Lavi.
This year’s crowd failed to top 300, but the event was postponed from its preferred date — April 5, International Pillow Fight Day. That day, the city held its 191st anniversary festival at Nathan Phillips Square, forcing the pillow fighters to delay the event.
Lavi’s goal is to eventually break the Guinness World Record for largest pillow fight, which is currently held by a fight in Minneapolis that took place in 2018. Over 7,600 participants showed up.
But the main reason for the event isn’t to break records, it’s to hopefully have a ripple effect in the community, Lavi said.
“For a limited time, we put all the differences aside and we just have fun,” he said. “I hope it helps people be more tolerant to each other and smile for each other.”

Toronto has a surprisingly long history of pillow fights. A pillow fight league operated out of bars along College Street in the late 2000’s to early 2010’s. In 2008, two University of Toronto students organized a pillow fight in New York that drew a crowd of 5,000 for the first World Pillow Fight Day.
Twoey Gray, a participant of Saturday’s pillow fight, said she fondly remembers attending a pillow fight league event over a decade ago.
“It was a time when these kinds of events were much more popular,” she said. “People were into these spontaneous acts of randomness.”
But at some point, events like that fell out of fashion, Gray said. She hopes events like the annual Toronto pillow fight are signalling a change in attitudes.
“I have noticed more and more people saying that they miss events like that, things that are organized in the spirit of togetherness and community and are free,” she said.
Lavi’s advice for people looking to drum up that kind of community is to put yourself out there.
“I'm always saying to people, if you have something that you would like to do in the city, go for it. Don't be afraid,” he said. “People will join you. People will support you. You'll be surprised by the amount of engagement and love that you get.”