A few prehistoric artefacts have been found in Cholesbury-cum-St Leonard’s, such as a Palaeolithic handaxe found in material transported to a road at Heath End. A Lower to Middle Palaeolithic handaxe was also found on a ploughed field at Buckland Common. Mesolithic tranchet axe-heads and Neolithic axe-heads have been found near Hadden’s Plantation and south-west of Heathend Farm. A Late Bronze Age sword was found at Hawridge Court Camp, even though the earthworks there are thought to be medieval.
Other earthwork monuments in the parish are prehistoric, such as Grim’s Ditch, which runs between Lanes End and Bottom Road and then between Leyland’s Farm and Shire Lane. Grim’s Ditch is a linear bank and ditch system that divides the landscape into territorial boundaries and probably dates to the Iron Age. The most striking monument is, however, Cholesbury Camp. This is an Iron Age hillfort that is made up of two large ramparts and dates to the Late Iron Age. Excavations in the 1930s uncovered some ovens, some of which may have been for metalworking. More recent excavations at a house called Overburnts on the edge of the hillfort have uncovered similar features. Another Iron Age metalworking site was found in St Leonard’s, at Dundridge Farm, and a slag heap of metalworking waste was found in Newset’s Wood.
The interior of Cholesbury Camp was taken over by a church, St Lawrence’s. It was first built in the thirteenth century but was rebuilt in the nineteenth, though its medieval character was retained. Recent geophysical survey suggests that there may have been a medieval village in the Iron Age hillfort. St Mary’s church, which is inside Hawridge ringwork, also dates to the thirteenth century and was rebuilt in the nineteenth. The ringwork is a type of castle and probably dates to the Anarchy period, a time in the twelfth century when there was civil war over the throne. The manor house there dates to the sixteenth century.
Dundridge Farm was the site of the medieval manor house in St Leonard’s. It is recorded in the Saxon period, too. There is a medieval moat at the farm, but the farmhouse is itself sixteenth century with later alterations, and seventeenth century wall paintings survive inside. The church in St Leonard’s is, unsurprisingly, St Leonard’s and dates to the fifteenth century. A hermitage belonging to Missenden Abbey was recorded here in the thirteenth century, however, and the church may have developed from that.
Some of the listed buildings in the parish date to the sixteenth and seventeenth centuries, including the Manor House and Erriwig Farm, High Chimneys and Boxtree Cottage. The windmill in Cholesbury is known as Hawridge Tower Mill and dates to the nineteenth century. It stopped working in 1916 and is now a house. Seventeenth and eighteenth century maps show a windmill in a similar position, but that was probably a previous incarnation.
In later centuries the area returned to the industrial character it had in the Iron Age. There were potteries here in the eighteenth and nineteenth centuries and several brickworks in the nineteenth and twentieth, on Buckland Common (owned by the Rothschilds) and Shire Lane. Many chalk, clay and gravel pits are recorded on nineteenth and twentieth century maps of the parish, at places like Newset’s Wood, near Bucklandwood Farm and at Hadden’s Plantation.