To some, the Yorkville area by Bay and Bloor was the coolest and most exciting place in Toronto during the 1960’s. There was an influx of creativity and musical talent to the area, and there were musicians from every genre (including folk, rhythm and blues, jazz and rock) who played in coffee houses and clubs in the Yorkville area. By the late 1960’s, there were at least 40 clubs and coffee houses in the area with live entertainment every night.

According to The Toronto Star, “an explosion of youthful literary and musical talent were appearing on small stages in smoky coffee houses, next to edgy art galleries and funky fashion boutiques offering hippie garb, blow-up chairs, black light posters and hookah pipes, all housed in shabby Victorian row houses”. Among some of the notable coffee houses and clubs in the area were the Riverboat, The Purple Onion, and the Penny Farthing.

Many have played at The Purple Onion coffee house including Gordon Lightfoot (as part of a duo called the Two Tones), Joni Mitchell, and Ian and Sylvia; and this is where Buffy Sainte-Marie wrote “Universal Soldier”. When the Two Tones split up, Lightfoot informed the owners of The Purple Onion that he was going solo and asked if they would still hire him, and they did.

The Riverboat was the most famous venue in the area, and featured performances by such artists as Neil Young, Simon & Garfunkel, Buddy Guy, and Tim Buckley; and had visitors such as Eric Clapton and Jack Nicholson (and it was rumoured that Bob Dylan visited the venue incognito). According to music journalist and author Nicholas Jennings, Joni Mitchell wrote “Night in the City” and performed her hit song “Both Sides Now” for the first time at The Riverboat, and Gordon Lightfoot wrote “Steel Rail Blues” at the venue. The Riverboat was open from 1964 until 1978.

Chez Monique’s had a house band called The Sparrows (who were later known as Steppenwolf), Rick James played at the Mynah Bird, and the Ugly Ducklings played at Charlie Brown’s. Other artists who have performed at the Yorkville coffee houses and clubs include Bruce Cockburn, Murray McLauchlan, and Dan Hill.

The music scene in Yorkville was thriving but while many loved the area, others felt the opposite, such as former Ontario MPP Syl Apps who felt that the Yorkville area was a “festering sore in the middle of the city” with many of the area’s visitors openly using marijuana and other drugs, and living what some considered to be an “amoral” lifestyle. The scene was also attracting large crowds of people including tourists, and the congested traffic made the air quality poor and was a threat to pedestrian safety.

On May 22, 1967, several locals in the area lead a “love-in” at Queen’s Park in an attempt to change public opinion that they were simply hippie drug addicts and “vagrants”, and to support shutting down traffic on Yorkville Avenue. More than 5000 people attended the “love-in”, and there were performances by Leonard Cohen and Buffy Sainte-Marie. According to the Global Nonviolent Action Database, there was also “the formation of a human chain in an effort to link the young and old generations together. In this way the hippies were using the nonviolent method of establishing a new social pattern”.

Following this, a “sit-in” (referred to as a “hippie brawl” by The Toronto Star–which it wasn’t, of course) was held on Yorkville Avenue on August 20th, 1967 where 300 locals sat in the middle of the street at 3:00 a.m. blocking all traffic, and approximately 2500 others stood and watched which added to the traffic disruption. Although it was a peaceful demonstration, it led to the arrest of 50 people for creating a disturbance and obstructing traffic.

This was the beginning of the decline of the “hippie revolution” in Yorkville. According to The Toronto Star, there was an increase in police presence in the fall of 1967 and a paddy wagon was parked at the corner of Hazleton and Yorkville during weekends. In addition, a 10:00 p.m. curfew was enforced by police for anyone under the age of 18.

To make matters worse, there were reports of an outbreak of “hippie hepatitis” during the summer of 1968 in Yorkville, as motorcycle gangs began selling heavier drugs in the area which led to vaccine stations being set up on the sidewalks. This led to many locals leaving the area.

A “free university” called Rochdale College also opened in 1968 at Bloor and Huron nearby. According to The Globe and Mail, the college was meant to meet a demand for housing, “all the while offering a free-wheeling social structure to contrast with the stuffy conventionalism of the outside world”. It remained open for seven years until it was closed due to defaulting on its mortgage, and it had gained a reputation as “a drug distribution epicentre ridden with bike gangs and squatters”; or according to The Toronto Star, “a hippie haven with easy access to drugs”.

By the 1970’s, the area began to transition into the high-end Yorkville that we know today. What a difference it was back then!

Here are a few videos of Yorkville back in the 1960’s (and 1970’s).

Yorkville in the 1960’s

Yorkville music scene in the 1960’s

Yorkville Hippies (1970’s)