Reading School was established shortly after the founding of Reading Abbey in 1125 by Henry I. In the early years, pupils were taught by Benedictine monks training young men for the priesthood. During its 900 years there have been various re-openings and changes in location, from the Abbey to the Hospitium of St John and later the site of the old town hall. Currently, Reading School is a single academy status grammar for around 1,000 boys, ranking in the top 5% of UK schools and is located on a 13-acre site off Erleigh Road.

Ken Brown and Chris Widdows, former pupils of the school, are prominent figures within the Reading School community through their involvement with the Old Redingensians Association (ORA). Ken serves as the ORA Archivist, while Chris is the Membership Secretary.