Prospect Hill is historically significant as the site of a number of the earliest farms in New South Wales, with a number of time-expired convicts settled on the land in 1791 by Governor Phillip. As a significant landmark on the Cumberland Plain, Prospect Hill provided an important reference point for early explorers from 1788, and played a role in the earliest exploration of the east coast of Australia. Prospect Hill is also associated with an important phase of Aboriginal/European contact; firstly through Pemulwuy's guerilla warfare in the area between 1797 and 1802, and in 1805 as the site of a reconciliation meeting involving Samuel Marsden.