Our History

The Early History of Oakwood Collegiate Institute

The first mention of our school was on August 22nd, 1907, when a plan was made to open a temporary high school to relieve overcrowding at Harbord Collegiate. The following month, four or five classrooms on the top floor of the King Edward School (now King Edward Junior and Senior Public School) at College and Bathurst were used to accommodate excess students from Harbord.  The temporary high school was named the “Harbord Annex”, and one of its teachers, W. L. A. Kennedy, was placed in charge.

In August 1908, a decision was made to erect a new high school in the northwest part of the city to accommodate the students and staff at the Harbord Annex, which was about to open for its second year atop the King Edward School.  The temporary school was officially renamed “North West High School”, and was now independent from Harbord Collegiate.  A principal was appointed, Mr. John L. Cox, and the school had nine teachers and 297 students.

After searching for a site on which to build a permanent building for the North West High School, the school board purchased 5 acres of woods and fields atop a hill overlooking the city on the southwest corner of Oakwood and St. Clair.  The cost of the land was $15,000, and in early 1910, tenders were placed in Toronto newspapers seeking bids for the construction of the new school building.

Now in its third year at the King Edward School, the fledgling North West High School “flourished in its unsuitable quarters”, even though classes needed to be dismissed at times which would not conflict with the elementary school housed on the floors beneath.  That summer, Principal Cox died following a brief illness, and was succeeded by Mr. R. A. Gray of Malvern Avenue High School.  Mr. Gray would remain principal for the next 21 years.

The New School

The land on which the new high school would be located was part of a large tract owned by Mr. Tom Bull.  Most of the land had been cleared near the school property, though a large wooded area remained to the east.  Two springs of clear water flowed across the land into the west branch of Garrison Creek, and a farmhouse was located at Oakwood and Burlington.  Some questioned if the school board was planning an agricultural college.

On a cold, wintry, windy day in March 1911, Mr. Gray visited the school and commented “despite exertions to make the building habitable, the sky was the only roof”.

The following September—still barely finished and now called “Oakwood High School—we opened at the muddy corner of St. Clair and Oakwood.  Designed by Franklin Belfry, the exterior featured Don Valley #1 Buff brick, while the foundation was set in Blue Beria Stone—one of the finest building stones in North America—shipped from a quarry in Beria, Ohio.  The closest streetcar stop was a half-mile south at the north end of Dovercourt, and the staff and students were required to walk up the muddy hill each morning—until Principal Gray had a plank sidewalk installed which lasted two years.  A parent complained to the local Trustee about their children’s arduous walk to the new school, to which the Trustee responded “the walk will do them good”.   There were 12 rooms on two floors, filled with 130 students and 12 teachers from Harbord.  To the west was a rustic area where—in the words of Principal Gray—“the little urchins from the public and separate schools in the region would dam the stream and make a very respectable swimming pool of it where they would bathe au naturel”.

Within the new school building, only eight of its 12 rooms were completed, and there was just one stairway to the second floor.  There was no roof over the auditorium, and workers continued their construction unceasingly while classes were in session.  Workers’ ladders were placed all about the school, and action needed to be taken because “boys would run up these ladders and walk across the steel girders 50 or 60 feet in the air”.

The New School Prospers

The fields surrounding the school were soon subdivided, and a streetcar was built from Avenue Road to Lansdowne which enabled easier access to the school.  In March 1912, Oakwood’s attendance boundaries were increased, though there was already “a tacit understanding that any student no matter where he lived might apply for admission”.

In September 1912, Oakwood became the first Toronto high school to offer “Manual Training” and “Household Science” courses.

On February 21st, 1913, the school celebrated its official opening, and the following year we were renamed “Oakwood Collegiate Institute”.

Ms. Jesse Greenaway, a classics teacher, fondly recalled:

Oakwood was different.  As soon as I got off the trolley car I knew it was different.  It was northwards towards the county.  The halls were not crowded.  It was spacious.


By 1915 there were 19 staff members.

The school was hit hard by The Great War, to which we sent 142 students and former students, only to have 108 return.  Five teachers also enlisted, including Miss Isabel Sutherland, who joined an American hospital unit in France, which was subsequently bombed with poison gas.  Sutherland died shortly after returning to Toronto.  Another teacher, Captain A. W. Dunkley, fought at Vimy Ridge, and was wounded at Passendale.  The Dunkley Scholarship is still awarded annually.

The new school quickly developed a reputation for excellence.  We had our first theatre production in 1914, won the senior rugby championship in 1917, and were noted for our outstanding Cadet Corps.

In 1919, a flu epidemic forced the school to close for a month.  That same year, Davenport Collegiate opened and took 100 students.  Oakwood was so overcrowded that two temporary buildings were erected to accommodate 160 students.

The 1920’s

During the 1920’s, two Oakwood grads took first and second place in the same year for having the top marks in Ontario, and Oakwood was described again and again as “a powerhouse”.  The Oakwood Oracle began publishing in the early 1920’s, and was noted for its literary excellence.  Frank Bear—who went on to receive a Ph.D. from the University of Chicago and became a renowned professor of New Testament Studies at Trinity College—was the Oracle’s first editor.  We had one of the best school libraries in Canada, and started both a Literary Society and a YWCA.  Oakwood had no cafeteria (even though "the technical school" had one), and because so much construction was being done in the early years, the lunch period was only a short recess.  When a change was proposed to create a full lunch period, parents objected.

By 1921 there were 30 staff at Oakwood, and that same year—with over 1000 students—Oakwood hired the first high school secretary in Toronto, Miss Ethel Rowland.  To relieve overcrowding, a third story was added in 1922 at a cost of $115,000.  This added 10 more classrooms, a cafeteria, a “gymnasia”, and a “swimming tank”.

Also in 1921, Norman ‘Red’ Ryan and his infamous band of thieves robbed the Bank of Nova Scotia on the southeast corner of Oakwood and St. Clair.  Manager Larry Oak was pistol whipped during the robbery, but regained his senses just as Ryan’s gang fled the bank.  Oak pulled an Iver-Johnson .38 caliber revolver from a tellers drawer and fired a warning shot as the thieves ran south on Oakwood Avenue--just as our students were leaving for lunch!

In 1923, Oakwood student Norman Endicott was awarded a Rhodes Scholarship, and within a decade Oakwood students had been awarded two more.

By 1924, we had 1,385 students, and Oakwood was “strict and proud”.  There was a strong military tradition, and male teachers used their military titles.  Students marched to class in pairs, boys shined their shoes, and church and religious services were part of the daily activities.  Lockers were separated by gender, and boys and girls both coveted the two adjoining lockers where the genders met.

Four movie theatres were built around the school: the Oakwood, north on Oakwood from St. Clair; the St. Clair, near Dufferin; the Paramount, in the block past Glenholme; and the Belmount, on St. Clair west of Dufferin.

The Crang family owned the land between Crang and Robina, and built “Oakwood Stadium” where the present No-Frills is located.  Students played team games at the stadium, and there were facilities for skating, swimming, football, and rugby.

Between 1921 and 1927, our rugby team won every championship.

Some notable events from 1927 include implementing a rotary system, starting the first music program in a Toronto school, winning the Cadet Corps championship, having the best girls’ choir in Ontario, and winning the Ontario dance competition.  That year we also prepared Christmas baskets for the needy, and were the first Toronto school to incorporate charitable work into the curriculum.

The 1930s

Our neighbourhood was hit hard by the Depression years.  A tent city was established in a field north of the school, while Tim Buck, leader of the Communist Party of Canada, lived nearby on Oakwood.  Earlscourt Park at Lansdowne and St. Clair was called “Poggy Park”, where many evicted unemployed lived in tents.  Several Oakwood students were forced to quit school and look for jobs to support their families.

In 1931, we again won the cadet championship, our Senior Literary Society disbanded, and the Oracle went from twice to once-per-year publication.

Our hockey team won the championship in 1933, and we held two assemblies per week, as well as after school tea dances, and an annual skating party.  The Oracle sold for 50 cents, and the local teen hangout was the soda bar in the St. Clair Drugstore at Crang Ave.

The 1940s

Oakwood was committed to the war effort.  The Oracle stopped publishing from 1943 to 1945, and no graduating awards were given during those years, as the girls did not feel it would be fair to the boys who were at war.

Our students knitted clothes for soldiers, and in 1942, our rifle team was the best in Canada.  Many names in the 1942 Oracle appeared again just a few years later on our plaque of war dead.

The 1950s

Our spirit of benevolence continued, and in 1950, funds raised from a performance of Pygmalion were donated to the newly-formed UNICEF.

We had an a capella choir, a current events club, and a stamp club.  The Cold War strengthened the Cadet Corps, and it was one of the only schools invited to the Toronto Armory for inspection.  To this day, Oakwood still has a rifle range deep in its basement.

Between 1950 and 1957, we had a contest which judged girls on posture and poise, and our boys had a cheerleading squad.

In 1955, we were one of two schools in Toronto associated with UNESCO.

In 1959—14 years following the end of WWII—our prom had a Japanese theme.  That same year, the new “old wing” of the school was built, with modern science labs.

The 1960s

A new cafeteria was installed, as well as a viewing gallery for the pool.  The stage was enlarged, and new seats were added.

In 1969, our Dress Code was amended to permit blue jeans, and to allow girls to wear pants.  We also started Toronto’s first Model United Nations.

The 1970s

Oakwood temporarily stopped holding school dances because they had lost their popularity.  We also opened a smoking lounge for students in the school basement, though it was quickly shut down due to inappropriate smoking behaviour.

Through the 1970s, the Barons and Lady Barons were the city champions at least once in every team sport, and in 1975, our junior girls took both the city volleyball and basketball championships.

The 1980s

Our spirit of benevolence continued with Oakwood organizing fundraising events to support UNESCO, Bolivian foster children, Covenant House, and the Ethiopian community.

In 1983, student Kamari Clarke co-founded the first Afro-Canadian club in a Toronto high school.

Thank you for taking the time to learn about our school’s proud history.

Written by Richard Nosov, Principal 2014-16