Joseph Backler was a young convict portrait painter, who arrived in Sydney in 1832. He was sent to the Port Macquarie penal settlement in 1833 after committing further offences in Sydney. His troubles continued in Port Macquarie. During his nine years there he received 150 lashes, a year in irons and 23 days in cells. 

Intriguingly, Backler has possibly included an autobiographical element in this otherwise impressive view of Port Macquarie. In the foreground are two figures — presumably convicts holding bottles — being pursued by three men. It is rare to see the underbelly of colonial life appearing in works of art.