The story of the school begins in 1666 when, according to legend, a sick, orphaned child was taken in and cared for by the landlord of the Rose and Crown in Twyford High Street. The child was Edward Polehampton who later made his fortune through portraiture and coach painting and became a prominent member of one of the City Guilds. On his death, he bequeathed money to a trust to establish a school in the High Street to clothe and educate ten poor boys of Twyford.
The legacy survives today in the form of the Polehampton Trust, which administers money left in the will of Edward Polehampton to be used for educational and charitable purposes in the villages of Twyford and Ruscombe.