For 8th grade in September 1930, the 13-year old Kennedy was sent fifty miles away to Canterbury School, a lay Roman Catholic boarding school for boys in New Milford, Connecticut. In late April 1931, he had appendicitis requiring an appendectomy, after which he withdrew from Canterbury and recuperated at home. In September 1931, Kennedy was sent to the Choate School, a private university preparatory boarding school for boys in Wallingford, Connecticut, for 9th through 12th grades, following his elder brother, Joe Jr., who was two years ahead of him. In January 1934 during his junior year at Choate, Jack Kennedy became ill, lost a lot of weight, was hospitalized at Yale-New Haven Hospital until Easter, and spent most of June 1934 hospitalized at the Mayo Clinic in Rochester, Minnesota for evaluation of colitis.
At 13, John Kennedy went to the Canterbury School, a private school in New Milford, Connecticut, but he fell ill and never returned. He later graduated from Choate Preparatory School in Wallingford, Connecticut, and in 1935 he entered Princeton University. Again illness forced him to leave school, but he resumed his studies the following year at Harvard University.