The most famous of these occurred shortly after the Norman Conquest of 1066 and involved the Trial of Penenden Heath, a dispute between Odo bishop of Bayeux, half-brother of William the Conqueror, and Lanfranc the Archbishop of Canterbury.

[1] The Domesday Book of 1086 subsequently recorded Pinnedenna as the place for the landowners of Kent to gather to receive notice in matters of administration at the shire court.

Wat Tyler led a mob gathered at Penenden Heath to Union Street in Maidstone in an early skirmish during the Peasants' Revolt of 1381.

[7] In 1828 the heath was again recorded as the site of a large gathering to debate the issue of "Protestant Ascendancy" before the passing of the Roman Catholic Relief Act 1829.

A detailed report of the assembly on 24 October 1828 by Richard Lalor Sheil describes the heath as a "gently sloping amphitheatrical declivity" and still, in the 19th century, the principal venue in the area for massing the populace.

[12] James Coigly, a United Irishman, was arrested en route to France carrying a letter addressed to the French Revolutionary Government calling for an invasion of England.

The last public execution on the heath took place in 1830, when John Dyke from the nearby village of Bearsted was hanged for burning a hayrick; it later emerged that he was innocent.

[16][17][18] During the 19th century the heath was slowly enveloped by the growth of the town of Maidstone, becoming a residential area at the junction of the main routes to Sittingbourne and Boxley.

[19] Odo de Bayeux was previously earl of Kent and the primary landowner of the region subsequent to his half-brother William the Conqueror's invasion of England in 1066.