Ludgrove was founded in 1892 by Arthur Dunn in Cockfosters, north London. Dunn was one of life’s natural enthusiasts and his favourite saying, “Whatsoever thy hand findeth to do, do it with all thy might” remains the school motto today. On Arthur Dunn's death in 1901, G.O. Smith and W.J. Oakley became headmasters and ran the school until 1934. Frank Henley then took on the headship, but soon handed over to Alan Barber and Tim Shaw.
In 1937 the school moved to its current site at Wixenford, Wokingham under an hour from central London. This new location would ensure that the founding rural character of Ludgrove would remain and gave great scope for growth and improvement. The school business was turned into a charitable trust in 1972. On the retirement of Alan Barber in 1973, his son Gerald and Nichol Marston became joint headmasters. Following the retirement of Nichol Marston in 2004 Gerald's son Simon Barber and Sid Inglis became assistant headmasters.
In July 2008, after thirty five years, Gerald and Janet Barber retired and Simon and Sid took over as joint headmasters. The school has expanded and developed enormously and it now has 185 boys, all boarding. In 2013 Simon Barber became the sole headmaster, he and his wife Sophie live at Ludgrove with their three young children, keeping the strong family tradition of the school.