There is evidence to suggest that a guild dedicated to the Blessed Virgin Mary was established in 1433 by Richard Neville, Earl of Warwick. In addition to the vicar, the guild maintained two priests in Brailes, one to be the precentor, and the other the schoolmaster for the “Fre Scole of Gramer for the Erudycyon and bring upp of dyvers and many pore Scolars”. The master’s stipend was £8 1s 8d, an endowment that continued for 500 years.
The royal commissioners carrying out the provisions of the 1547 Chantries’ Act of Edward VI found that a “Grammer Scole hath been continuallye kept in Brailes” and ordered its continuance with John Pittes as master, at the old salary of £8 1s 8d. The rest of the old guild endowment was confiscated by the Crown at the dissolution of monastic orders during the Reformation.
In letters patent of October 27th 1581, Elizabeth I granted the Rectory of Brailes in fee-farm to Edmund Downing and Peter Ashton, who paid the annual rent of £11 18s 4d plus £8 1s 8d for the salary of the schoolmaster. The owners of Rectory Farm thus began their responsibility not only for the maintenance of the chancel of the Parish Church, but also for the support of the Free School.
By indenture of feoffment dated October 20th 1620 between the following gentlemen: Barnabas Bishopp and Timothy Harris of Brailes, Richard and Edward Croft of Sutton under Brailes, together with Robert Davies, John Harris, William Poole and John Stock, all of Brailes; substantial lands and properties were assigned to a perpetual trust in order to “repair, amend and build (the Parish Church of St.George) in such manner as should be thought meet by the churchwardens and some of the chiefest inhabitants of the said town” and also to provide for the “relief and maintenance of the free school and schoolmaster”. Two of the feoffees or trustees were to be elected as reeves or rent-collectors and the accounts rendered yearly at the Church on St.Luke’s Day, October 18th.