Cholesbury stands at the crossroads of several droving routes, the Commons providing a safe place to rest their animals. In turn this regular traffic supported local trades and several alehouses over the years. By 1753 The Castle, the Maidenhead (later the Bricklayers Arms), next door to it the Queen's Head and The Slip Inn were operating for at least a period. They were able to flourish due to the boost in trade between the 18th and the early part of the 20th centuries when they were also frequented by the growing numbers of brickyard and agricultural labourers. None of these public houses has survived to the present day.