It was first settled by Europeans in 1794 in a bid to acquire arable land to feed the increasing population of the penal colony at Sydney. In April 1794, Lieutenant Governor Francis Grose submitted plans for the first 22 farms on the Hawkesbury River in the present Pitt Town Bottoms area. In June 1795 a camp of aborigines opposing the landtakings was harassed by a British regiment commanded by Paterson (who later regretted the necessary injustice).

By 1811 Governor Lachlan Macquarie established the five Macquarie Towns in the area. They are Windsor, Richmond, Castlereagh, Wilberforce and Pitt Town. Many of the early 19th century buildings still survive today. Ebenezer has the oldest surviving church and school building in Australia. Windsor District Council was formed in 1843 and disbanded in 1846. In 1871 the Borough Council of Windsor was founded and the Richmond Borough Council followed in 1872. The two Councils amalgamated in 1949 to become Windsor Municipal Council. Colo Shire Council was established in 1906 and joined Windsor Municipal Council in 1981 to become Hawkesbury Shire Council. In 1989, Hawkesbury became a City.