The site of Port Macquarie was first visited by Europeans in 1818 when John Oxley reached the Pacific Ocean from the interior, after his journey to explore inland New South Wales. He named the location after the Governor of New South Wales, Lachlan Macquarie.
Oxley noted that 'the port abounds with fish, the sharks were larger and more numerous than I have ever before observed. The forest hills and rising grounds abounded with large kangaroos and the marshes afford shelter and support to innumerable wild fowl. Independent of the Hastings River, the area is generally well watered, there is a fine spring at the very entrance to the Port'.
In 1821, Port Macquarie was founded as the first penal settlement, replacing Newcastle as the destination for convicts that had committed secondary crimes in New South Wales. Newcastle, which had fulfilled this role for the previous two decades, had lost the features required for a place for dumping irredeemable criminals, that being isolation, which was lost as the Hunter Valley was opened up to farmers, and large amounts of hard labour, which had diminished as the cedar in the area ran out and the settlement grew in size. Port Macquarie, however, with its thick bush, tough terrain and local aborigines that were keen to return escaping prisoners in return for tobacco and blankets, provided large amounts of both isolation and hard labour to keep the criminals in control. Under its first commandant, Francis Allman, who was fond of the flogging, the settlement became hell, where the convicts had limited liberties, especially in regard to being in possession of letters and writing papers, which could get a convict up to 100 lashes.
Due to the lack of liberties of the settlement, Ralph Darling, governor of New South Wales, quickly sent many 'specials' or literate convicts with a decent education who had voiced negative views about him. Later on in the settlements history, in the 1830s, disabled convicts started to
