For four decades, a boys’ preparatory school on the edge of the Downs in Eastbourne educated an astonishing roll call of future talent — the writer George Orwell, the critic Cyril Connolly, the photographer Cecil Beaton and more. It also inspired one of the most famous — and most damning — essays about English schooling ever written. This is the story of St Cyprian’s School.
A cramming-ground for Eton
St Cyprian’s was founded in 1899 by a young married couple, Lewis Vaughan Wilkes and his wife Cicely, and named after an early Christian bishop of Carthage — a nod to the school’s earnest, “muscular Christian” ethos. It began in a large house on Carlisle Road, but by 1906 had grown enough to move to purpose-built premises with extensive playing fields behind Summerdown Road, in the shadow of the South Downs.
It was an expensive and exclusive establishment with one overriding purpose: to drill its boys hard enough in Latin, Greek and mathematics to win scholarships to the great public schools like Eton and Harrow. It was very good at it. To boost its record still further, the school quietly took a few exceptionally bright boys on reduced fees — a policy that would, quite by accident, help make it famous. The pupils knew the headmaster as “Sambo” and his formidable wife, who ran the domestic side and taught English, as “Flip”.
A remarkable roll call
What sets St Cyprian’s apart is the sheer concentration of future talent that passed through its doors in a few short years. Its Old Boys included the writer George Orwell (then plain Eric Blair), the influential literary critic Cyril Connolly, the celebrated society photographer Sir Cecil Beaton, the naturalist and author Gavin Maxwell (of Ring of Bright Water fame), and the golf writer and broadcaster Henry Longhurst — with the politician and diarist Alan Clark among later pupils. That one small seaside prep school shaped so many notable lives is remarkable by any measure.
Did you know? Orwell and Cyril Connolly were at St Cyprian’s together and went on together to Eton — the beginning of a literary friendship that lasted the rest of Orwell’s life.
The school Orwell never forgave
Three of the school’s writers left accounts of it — and they could hardly disagree more. Cyril Connolly described it in his 1938 book Enemies of Promise, thinly disguised as “St Wulfric’s”. He poked fun at the Wilkeses and the cult of character-building, but concluded that the school had done him a world of good.
George Orwell felt very differently. In his bitter, quasi-autobiographical essay Such, Such Were the Joys, he painted the school as a place of cold dormitories, poor food, snobbery and casual cruelty, and used it to attack the whole Edwardian system of sending small children away to board from the age of seven or eight. So sharp was the essay that, for fear of libel, it could not be published in Britain until long after those it described had died; it first appeared in the United States in 1952 with the school’s name changed. Fellow Old Boy Cecil Beaton, who read it, judged it hilariously funny but exaggerated — and later scholars have questioned how fair Orwell’s portrait really was. Connolly himself, after reading it, sprang to the school’s defence and felt his own gentle criticisms had been unjust.
Whatever the truth, Orwell’s Eastbourne years clearly left their mark on his fiction. The village in Animal Farm is named after nearby Willingdon, and the atmosphere of watchful, all-powerful authority that pervades Nineteen Eighty-Four has often been traced back to his schooldays on the Sussex coast.
Fire, decline and a blue plaque
In its fortieth year, disaster struck. On 14 May 1939 the main school building was gutted by fire, and in the blaze a young housemaid tragically lost her life. The school moved first to temporary premises in Eastbourne and then out of the town altogether, to Sussex and briefly beyond, as wartime requisitioning and dwindling numbers took their toll. It never returned, eventually merging away, and its playing fields were sold to Eastbourne College.
Today a blue plaque at 65 Summerdown Road — once the headmaster’s house — commemorates the school’s famous pupils, naming Beaton, Connolly, Longhurst, Maxwell and Orwell. The building has since found new life as a community and creative space. It’s a quietly extraordinary spot: an ordinary Eastbourne street corner that helped shape 20th-century English writing.
St Cyprian’s School: FAQs
Where was St Cyprian’s School?
It was a boys’ preparatory school in Eastbourne, East Sussex, based from 1906 in purpose-built premises off Summerdown Road, near the South Downs. It operated from 1899 until a fire in 1939.
Which famous people went to St Cyprian’s?
Its Old Boys included George Orwell, Cyril Connolly, Sir Cecil Beaton, Gavin Maxwell and Henry Longhurst, with Alan Clark among later pupils — a remarkable list for one small prep school.
Did George Orwell go to school in Eastbourne?
Yes. Eric Blair — later George Orwell — attended St Cyprian’s in Eastbourne from 1911 to 1916, before winning a scholarship to Eton. He later wrote a famously critical essay about the school, Such, Such Were the Joys.
Can you visit St Cyprian’s today?
The school no longer exists, but a blue plaque marks the former headmaster’s house at 65 Summerdown Road, honouring its famous pupils. It’s on a residential street, so please be respectful of the current occupants and neighbours.
Explore more Eastbourne stories: George Orwell in Eastbourne, the painter Eric Ravilious, and the wider history of Eastbourne.