Canterbury was founded in 1915 on the aspiration of two men: Henry O. Havemeyer, scion of a wealthy family which made its fortune in sugar refining, and Nelson Hume, a Catholic schoolmaster.

They intended to establish a Roman Catholic school where young men could be guided in their religion and be prepared to attend Ivy League universities.

From its start with 16 enrolled students, Nelson Hume guided the school through two world wars and the great depression until his death in 1948.

He was succeeded as headmaster by Walter Sheehan, John Reydel in 1973, Roderick Clarke in 1978, Thomas Sheehy in 1990, and Rachel E. Stone in 2016.

Each residence hall contains faculty apartments that range from the size of town houses to smaller one-bedroom suites.