How Yorkville's hippie music scene propelled the late Gordon Lightfoot to fame

If you took a stroll past the aging Victorian homes-turned coffee houses that line the streets of Toronto's Yorkville neighbourhood in the 1960s, there was a good chance you might spot Gordon Lightfoot.

The area that's now largely associated with couture shopping and pricey dining options once served as a launch pad for the city's counterculture, hippie movements, and folk music revival that catapulted many artists into stardom, including Lightfoot. 

And as Canadians honour the folk music legend who died Monday, it's crucial to understand the singer-songwriter's roots and loyalties were deeply tied to Toronto, particularly the folk music scene in Yorkville, music historians told CBC Toronto.

"So many musicians were playing there, Neil Young, Joni Mitchell, Ian and Sylvia and Gordon Lightfoot. That was the 60's folk singer-songwriter scene … that's when Gordon Lightfoot started to be heard," said Robin Elliott, the Jean A. Chalmers Chair in Canadian Music at the University of Toronto.

Where Lightfoot rose to fame is a very different Toronto than we know today, Elliott said. 

In the 1960s, Yorkville's coffee houses were reminiscent of the Haight-Ashbury neighbourhood in San Francisco, which was a centre for hippie counterculture at the time, said Elliott. 

Elliott recalls going to Yorkville as a teenager and seeing houses decorated with psychedelic colours with drug paraphernalia being sold, and everyone was smoking. These coffee houses were dimly lit spaces that housed discussion and music well into the night. 

"The coffee houses drew customers in having live musical acts," he said. At the height of the scene in the late 1960s, artists including Lightfoot would often perform.

"He became well known through his participation, a member of the Yorkville scene," said Elliott. 

In the 2019 CBC documentary If You Could Read My Mind about Lightfoot and his life, the musician said that "Yorkville was it's own little community." The film highlights the hold Lightfoot had over the coffee house attendees, who were blown away by his vocals and lyricism. 

However, Lightfoot's image at the time was not the shoulder-length grey hair tucked behind his ears that featured prominently in his obituaries this week. He looked like a "slightly older church choir boy" while performing in Yorkville, Elliott joked. 

Later, he "let his hair down" but still within limits, said Elliott. Though he was part of the hippie Yorkville scene, he didn't entirely fit in and wasn't known as a particularly radical member, he said. At this time Lightfoot was known more as a prolific songwriter, rather than a singer. 

But his impact on the neighbourhood and the folk revival movement was strongly felt across the city. Lightfoot was very involved in the Mariposa Folk Festival on the Toronto Islands, which often scouted artists from the Yorkville scene, said Stacy Allison-Cassin, an assistant professor at the school of information management at Dalhousie University.

Allison-Cassin launched a website with students at York University in 2017 on the Yorkville coffee house scene, which includes information about Lightfoot's affinity for the Riverboat Coffee House.