In 1381, southern and eastern England were in a state of discontent. There were many reasons: the failure of the French Wars; the Labour Laws following the Black Death; the desire of villains to be free of labour services and feudal dues.
However, the spark was fanned to a flame by a poll tax levied on every lay person, male and female, over the age of 15. The procedure of the tax was disappointing, and the Commissioners were ordered to enquire how each township had been taxed. A court was held in Brentwood on 30 May 1381 and, following a riot, the Commissioner, Thomas Bampton, was driven from the town.
Sir Robert Belknappe, the Chief Justice of the Common Pleas, was sent to restore order and punish the 'evildoers', but he was seized by a mob and forced to leave the town. Before departing, he was forced to give the names of the jurors who had 'presented' the names of the original rioters. Those the mob could catch they beheaded, together with tree clerks of the Commissioner. The rebels then joined the Peasants' Revolt, led by John Bull and Wat Tyler in London. After the death of Tyler, the rebels were defeated at Billericay.
After these events, Brentwood sank back into itself. For the next 150 years it was a small market town under strong ecclesiastical influence, for the Church was the chief landowner.
The Reformation and the Dissolution of the Monasteries brought about great changes and, after passing through various hands, the twin manors of South Weald, Costed and Caldecots, became the property of Antony Browne. He founded Brentwood School (pictured below today) and almshouses at South Weald.
The religious struggles of the time left their mark. In 1555, William Hunter was burned 'at the town's end where the butt stock' for his religious beliefs. He had argued with Thomas Wood, the Vicar of South Weald, as to the nature of the communion.