Oakville's first school was formed in 1836 and was called the Oakville Common School, only nine years after William Chisholm established the community of Oakville. The school was on Navy Street where the Oakville Public Library now stands. Students primarily learned how to read, write, and spell along with some math, history and geography.
The Common School's enrollment list was rapidly growing. Newer, bigger schools were going to be needed. In 1850 the Oakville Common School moved to a new, larger building just north of the first one. Oakville's first Grammar School was two rooms attached to the side of the Common School in 1854. Since there were now two separate schools under one roof, the building was nicknamed the Union School. The New School Law Improvement Act of 1871 changed the terminology that had been in use. Common schools were to be called Public schools, Grammar schools became High schools and Headmaster became Principal.
The 1900's brought new changes to the schools. Most schools replaced their wood stove heating with coal, curriculums became more standardized, and schools had a more diverse selection of courses and were better equipped. The old Grammar School was now much too small and so it was redesigned by architect Alfred Chapman and built on Reynolds Street. The cornerstone of Oakville's second high school was laid in 1908.
During World War I, the Oakville High School promised to help the war effort by growing beans. The fields were transformed into giant bean fields tended by student volunteers. Sadly the number of volunteers dwindled to just two, Margaret Turner and Frances Robin, who finished the project off by themselves to the end.
At this time the school began to make some changes; the dress code was relaxed and many different sports and clubs were formed. Rugby and Hockey were the most popular and games often had a huge turnout of supporters. Debating, music recitals and dramatics were also popular clubs, but the most popular change was the allowance of dances! Up until then dances were not allowed in the school.
When WWII started, many young students enlisted and went overseas to fight. Sadly, many never returned. The students at OT have assembled a book of remembrance to preserve their stories.
In 1946 the school district of Trafalgar merged with the district of Oakville and the high school was renamed to Oakville Trafalgar High School. The school had come a long way since 1908. There had been several new additions such as science labs, gyms, and classrooms. The plot of land beside the school was also bought to accommodate these new rooms.
In 1992 the school was again too small and starting to age. It was moved to the current location, a new, modern building on Devon Road.