The School was endowed out of the revenues of the newly dissolved ecclesiastical colleges of St Mary’s and St Chad’s, on the petition of Richard Whittaker, a rich Shrewsbury clothworker and bailiff, and Hugh Edwardes, a London mercer born near Ellesmere of an ancient Welsh family.
The Royal Charter provided for a master and an usher to be appointed by the Corporation to provide a free grammar school education to all comers. The School was to be governed by regulations agreed between the Corporation and the Bishop of Lichfield.
In anticipation of the Charter, property was acquired for the future school near the Castle. However, it was another nine years before the Revd Thomas Ashton, generally regarded as the first Headmaster, took up his post.
Thomas Ashton was born in about 1500 and was an early graduate of St John’s College, Cambridge, of which he was a resident Fellow 1521-41. This college was one of the key centres of the Protestant reformation and by the time he came to the hitherto Catholic town of Shrewsbury in about 1561, Ashton had a reputation as a powerful Protestant preacher with influential friends at Court. Ashton worked closely with the town authorities and became in effect the first Protestant 'public preacher' in Shrewsbury, having a major impact not only on the growth of Shrewsbury School but also on the religious history of the town.
During his time as Headmaster, the School was described by William Camden in his book Britannia as "the best filled in all England, being indebted for [its] flourishing state to the provision made by the excellent and worthy Thomas Ashton. Besides the children of the gentry of this county and North Wales, many of the first people of the kingdom sent their sons there."
Ashton's most famous legacies to both town and school were arguably his Whitsuntide and Passion plays, which were performed in a semi-circular amphitheatre (now the site of the town's Quarry Swimming Pool). They were extremely popular, attracting audiences from far and wide across the county, probably numbering several thousand.
It may have been in one of those productions that a young pupil named Philip Sidney – who joined the School in 1564 and later became the renowned Renaissance soldier, statesman, diplomat, poet and earliest famous Salopian – made his first dramatic appearance.
In the latter years of his headmastership, Ashton was able to increase the endowments to the School and lay down a series of ordinances, or rules for its governance, which lasted until 1798. These brought about the further expansion of the School, including the construction of a new school building on the site of the original – where the School remained until its move to Kingsland in 1882.
(With acknowledgement to 'Shrewsbury School 1552 - 2002' by Robin Case and www.shrewsburylocalhistory.org.uk)