Bridgnorth Endowed School was founded in 1503, in the reign of Henry VII, established as a ‘common school’ by the Corporation of the Borough of Bridgnorth.

The revenues of the Chantries of St Leonard’s Church were originally used to support the school. An annual payment of £8 from the Exchequer was assigned in perpetuity ‘to a Schoolmaster keeping a grammar school’ at Bridgnorth after the dissolution of the Chantries in 1548 during the reign of Edward VI.

A barn, which had been used as the chapel of St John the Baptist (the new Bridgnorth Town Hall was also built in 1652 using material from a dismantled barn), first housed the school. This stood on the north side of St Leonard’s churchyard outside St Leonard’s Church.

By the end of the sixteenth century the former chapel of St John the Baptist was being described as the ‘old school-house’. The former chapel of St John the Baptist was replaced in 1595, in the reign of Elizabeth I, by the present building in St Leonard’s Close known as the ‘Old Grammar School’ .

This building appears to have been erected by Sir Rowland Haywood, a sixteenth century inhabitant of Bridgnorth who made a name for himself in business in London and became Lord Mayor of London and a Member of Parliament for the City of London. Indeed, Sir John Haywood in his will of 1635 refers to the School as having been founded by his father, Sir Rowland.

Sir Rowland appears to have charged a property at Bridgnorth with an annual payment of £20 to the School, a payment later rendered by the Apley estate after Sir William Whitmore’s purchase of the land in question in 1623. In 1785, during the reign of George III, the ‘Old Grammar School’ was renovated with gifts of £200 each given by the town’s Members of Parliament, Major Whitmore and Admiral Pigot.

The ‘Old Grammar School’ building still stands in St Leonard’s Close and is currently occupied by contact centre Unity 4.