1847 - 1863
In the early 1800s, education in Scarborough was not very well "established". There was only one school, set up in a primitive building. By 1847 however, Scarborough had grown to the point where something more organized was required, so 16 School Sections were established; SS # 6 included the Woburn Community. At this time, a school, also designated SS # 6, was erected on Markham Road, just north of the 2nd Concession (Ellesmere Road). This one story frame structure was 23' x 33'. Several windows provided light and a wood stove provided heat. Between 1850 and 1862, Alexander Muir taught at SS #6. He composed "The Maple Leaf Forever", which for many years was Canada's unofficial national anthem. This is why the maple leaf is part of the school crest. By 1862, a larger school was required, so the frame structure was moved to Old Danforth Road and converted into a house.

1863 - 1956
In 1863, a brick school was built on the site where the frame building had stood. An attractive structure, it had cream-coloured quoining on the corners and around the gothic windows. In 1895, an addition to the back of the building expanded it to two rooms. A few years later, the convenience of two outdoor privies was finally added. The school operated this way until 1956. By then, though, the old school just could not keep up with the demands of modern education. SS #6 was boarded up and the students were sent to Golf Road P.S. Consideration was given to turning SS #6 into a museum, but by 1963 extensive repairs were needed. Finally, just before the new Woburn C.I. was opened, the old school was demolished. During the demolition the 1863 date stone was discovered to be, in fact, a tombstone for Thomas Hubbard, who died in 1850. It is believed that a stone-mason made an error on the tombstone and then decided to use the other side as a datestone for a cost-conscious school board. The school's bell was also salvaged and presented to the new school. It became a tradition of the graduating Grade 13 class to steal the bell. The bell has vanished and it appears that the Grade 13's are not to blame. The bell was borrowed by the Board of Education but returned to Woburn Jr. There, early in 1980 or 1981, persons unknown picked it up.

Woburn C.I. 1963 - present
In the spring of 1963, while the fate of SS # 6 was being decided, a brand new Woburn was nearing completion. Designed by architects Parrott, Tambling and Witmer, this new school incorporated all the features that modern education required. Built at a cost of $15 million, the school contained 27 classrooms, a double gym / auditorium and a cafeteria that could seat 650. Situated on 15 acres, there was plenty of room for a quarter-mile track and a playing field, with space left over for future expansion. In 1963, when the school opened, it was projected that attendance would reach the 1500 level. The population was expanding rapidly. It was not long before it became apparent that expansion would be needed. In may of 1967, the first new wing opened and Woburn received its auditorium. The science wing stretched across the back of the school and created what is officially called the Woburn Centennial Square, but commonly known as the Quadrangle or the Quad. A Walkway existed from the back parking lot into the quadrangle and, until 1987, was the site of the Smoking Lounge, a dark, dingy place when the exterior doors were closed. Over the years there have been other additions - music coridor and the tech wing, including the auto shop (70-71) - to meet the growing and changing needs of the students. Woburn C.I. soon surpassed the projected enrollment. At its height, in the early 1970s, the school had about 2,400 students and 14 portables besides its various additions. Throughout the 70s and the early 80s, the school remained "above projections". With its Gifted Program drawing students from all across Scarborough, its adult classes, its popularity because of its academic and sports record, its ESL program and its general image as a successful and congenial place to be, it draws many students from outside its boundary, Woburn has remained above enrollment projections. In 1987-8, with enrollment hovering near 2,000 mark, saw the return of 3 portables, something almost unheard of for an established school.