“(People) have wound their way to Yorkville for the same reasons. They are the restless ones, the angry ones.”

This is how Toronto Star reporter Wendy Darroch described Yorkville and its frequenters in 1966.

The following year, the Star reported that the Yorkville Village Association penned a letter to the mayor at the time, requesting that the city hire experts to look into the hippies in the area.

With the current mini-boom in U.S. hippy nostalgia, from the 50th anniversary of Woodstock to the Quentin Tarantino film Once Upon a Time in Hollywood to the Mindhunter series on Netflix, it’s easy to forget that Toronto had it’s own hotbed of ’60s culture: Yorkville.

What is now one of Toronto’s most expensive neighbourhoods was once a hot spot for youth looking to rebel and create a lifestyle of their own.

Yorkville was “where the discipline of parents, the strain of formal education and the hypocrises of an adult world are discussed, chewed, rebelled against,” Darroch wrote. “It is here they can meet on common ground. They share the same problems, the same lust for independence, the urge to be heard; it is here they find understanding, a common bond.”

At one point, city council considered a ban on coffee houses and entertainment spots where people would hang out to discuss politics and culture among other things.

Paul Federico was a teenager living in Leaside in the late ’60s and the early ’70s. He would often hang out in Yorkville, a neighbourhood which he described as the place in Toronto where you could show off your rebellious streak.

“While I was there, between ’69 and ’70, if you wanted to piss off your parents, the government, and the authorities, that’s where you went to hang out,” said Federico, the president of the Toronto Historical Association. “Even if you never smoked a joint in your life, you had to be there to claim to be there.”

Yorkville’s notorious reputation was exemplified in a 1966 Star article that showed David Rotenberg, a city councillor, peering over fences into backyards, hoping to catch youthful ne’er-do-wells in action.

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With dirt cheap bungalows and tiny one-and-a-half story houses crammed side-by-side, Yorkville was a neighbourhood for people “on the fringe,” according to Federico. “They made their own entertainment,” he said. “It was the perfect place for the counterculture and the hippies.”

But eventually, after a decade or two, the neighbourhood lost the wayward young people, the anti-establishment atmosphere, the political cafés, and transformed into something else.

“Developers came in, and seeing that they could trade-in on the ambience and image of Yorkville, began to build up,” Federico remarked. “Instead of selling hippie clothes, soon they were selling Gucci shoes.”

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By 2007, Star reporter Chris Sorenson noted that the Yorkville of yore was no more. Once the epicentre of counterculture and anti-establishment sentiments in Canada, it became the playground for the city’s wealthy. For Sorenson, the current neighbourhood can even be seen as a metaphor for the hippie movement.

“It began as a rebellion against and its values ended up becoming swallowed by popular culture,” he wrote.

Listen to the full story by Wendy Darroch from 1966.

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Jacob Lorinc is a breaking news reporter, working out of the Star's radio room in Toronto. Follow him on Twitter: @jacoblorinc

Ilya Bañares is a breaking news reporter, working out of the Star's radio room in Toronto. Follow him on Twitter: @ilyaoverseas