[2] There has been an educational facility at the current site of the school since at least the early thirteenth century - established by the Guild of the Holy Cross.

The School can trace its origins to May 1295, when in the Register of Deacons of the Diocese of Worcester there is the record of the ordination of Richard as rector scholarum, to teach the basics of learning the alphabet, psalters, and religious rites to boys.

A schoolroom, schoolhouse and payment of £20 per annum for a master was one of the provisions of King Edward VI's charter which established Stratford-upon-Avon as a borough in June, 1553.

The school's current Headmaster is Mr. Bennet Carr MA FRGS, and the Chair of Governors, Mr Victor Matts.

There are a variety of architectural styles on the site ranging from the fifteenth-century Guildhall to the Denis Dyson science building opened in 2008.

The ground-floor of the Guildhall, where the town council of Shakespeare's time met and where travelling players performed - the holes for the rods to hold the temporary stage are still visible - was used as a library until February 2013.

Pedagogue's House, first built in 1427 and believed to be the oldest half-timbered schoolroom in England,[15] is attached to the Old Vicarage where the Headmaster lives.

The most recent part of the school, built in 2017, is the Richard Spender Building, a three-storey block which offers new English classrooms, computing suites, and a library named after old boy Tim Pigott-Smith.

The Levi Fox Hall, named after a Chairman of the Governors, is primarily used for sport, assemblies, school plays, concerts and examinations.

[17] Students take part in fencing,[18] athletics, rowing, hockey, basketball, badminton, table tennis, volleyball, netball and previously fives.

[19] The music department holds termly concerts and the King Eddie's Revival Big Band are frequently featured.

The school puts on an annual play; in 2005 the production was Unman, Wittering and Zigo, in 2006 Shakespeare's The Winter's Tale, in 2007 an adaption of Simon Armitage's The Odyssey, and in 2008 The Resistible Rise of Arturo Ui.

Established and run by deputy head Perry Mills, this theatre group developed out of the school's involvement with Michael Wood’s documentary series In Search of Shakespeare.