Despite being well placed in his twenties to pursue a distinguished academic career, Carrington chose teaching, first at
Haileybury in Hertfordshire, and then at
Dulwich College as Senior Classics Master. Then in 1937, in his early thirties, he was appointed to the headship of St. Olave's and St. Saviour's Grammar School. In 1939, with war imminent, he married Charlotte Chalmers. As headmaster of St. Olave's during the Second World War, he oversaw the evacuation of the school away from the bombing of London, initially to
Uckfield and
Buxted in Sussex, and then to
Torquay (1939–1945). In 1948 he received the Medaglia di Benemerenza from the Italian government, honouring him both as an educationalist and as an archaeologist. (The date, 13 June 1948, marked the bicentenary of the excavation of Pompeii.) Following the war the school made steady progress under his leadership. It was during his tenure that the decision to move St Olave's from its inner-city location near Tower Bridge to suburban Orpington was made (1957), and the move was realised in 1968 while he was still headmaster. However he was an authoritarian figure, not well liked by his pupils. Helped by St Olave's Antiquarian Society, he wrote a history of the school, ''Two Schools: A History of the St. Olave's and St. Saviour's Grammar School Foundation''. A short interim volume of the history was published in 1962 for the quatercentenary of the charter of St Saviour's Grammar School. The fuller second edition was published by the governors of the foundation in 1971 in commemoration of the quatercentenary of the charter of St Olave's Grammar School. The onset of illness in 1970 prevented Dr Carrington from completing the book, despite having "completed the writing of almost all of the text before this". The supervision of the final stages of preparing the book was taken over by E. S. Wood, secretary of the Antiquarian Society, and by J. R. Hawkins, the acting headmaster. The book includes an account of Carrington's own career at St Olave's, written presumably by Hawkins and/or Wood. He was the general editor of The Alpha Classics series published by
George Bell & Sons. Dr Carrington died the following year aged 65. == Works ==