Pitstone Windmill was used from its earliest days to mill grain, grown in the nearby villages, into flour. Village mills like this one were once an essential service within a community so it is no surprise that the mill has a history of providing a lucrative income for its owners and tenants.
Although the industrial revolution began to undermine the importance of a local mill through the advent of mass production, investment in the Pitstone Windmill continued.
During the 19th century much of the machinery was replaced by the Canal Company, who owned the mill until 1842, or by Francis Beesley, who sold it for £400 in 1874 to the third Earl Brownlow, owner of the nearby Ashridge Estate.
Lord Brownlow subsequently let it to a local farmer, Hawkins of Piston Green Farm who ran a successful business from it and oversaw further repairs in 1895.
In 1902 a fierce gale caused extensive damage. The sails were not turned in time and blew forward, causing the tail bearing to fly through the roof and the sails to crash into the round house walls.
This event put the Pitstone Windmill beyond economic repair and it was left to decay. A combination of the elements and opportunists caused the loss of many of its constituent parts.
In 1924 the Ashridge Estate was broken up and the mill was sold off. Pitstone Windmill was bought by its tenants, the Hawkins family.
The Hawkins were unable to save the windmill themselves and in 1937 they donated it, and access to it, to the National Trust.