punishment in 1821, but wound down to make way for free settlers in 1830. As a penal settlement it may be compared with the first settlements at Sydney, Parramatta and Norfolk Island, all of which were commenced in 1788. Port Macquarie shares many institutions and public buildings in common with these first settlements. A progression can be seen from Newcastle to Port Macquarie and finally Moreton Bay, in order to maintain the isolation of the penal settlements from the expanding free population. The early 19th century development of the town shared many features in common with other similarly dated towns in New South Wales. A more unusual factor is the continuation of some of the institutions of the penal settlement to the mid-1840s Cottages 1–5 were probably built in 1823, to house the newly appointed Assistant Superintendent and Free Overseer. Cottage 1 was occupied by the Deputy Superintendent of Convicts up to 1830. By 1831 it was occupied by the Superintendent of Convicts, his original residence now being used for other purposes. The last known use during the 1830s was as the Survey Office, before demolition, since it lay within the newly laid out grid of streets. Cottages 2 to 5 were Overseer's Cottages. Cottage 2 was occupied in 1831 by William Branch, who had been an overseer from 1823 to 1832. During the later 1830s the house was used as the Police Clerk's Quarters, before being demolished, as it too was within the newly laid out street. Cottage 3 was the Post Office by 1831, later also the Police Clerks Quarters and then the residence of the Clerk of the Court, possibly until the 1850s or 1860s. After 1830, Cottage 4 (only partly on the subject site and not excavated) was used as a hotel, "The Settlers Arms", run by Charles Farrell, the second hotel license for Port Macquarie in 1830. Cottage 5 lies to the west of the site. The cottages on the subject site are closely related to the function of the penal settlement from 1821 to 1830. With the changeover from penal settlement to town, they were either associated with the continuation of penal institutions in Port Macquarie until the 1840s or the development of the town until the 1860s. The site continued its association with the cultural life and administration of the town with the construction of the School of Arts in 1884 and the