Overseers' Cottages Remains is a heritage-listed archaeological site, now incorporated into the Glasshouse entertainment centre, at 30-44 Clarence Street, Port Macquarie, Port Macquarie-Hastings Council, New South Wales, Australia. It is the remains of cottages for convict overseers', built from 1823 to 1830 by convict labour. The property is owned by Port Macquarie-Hastings Council. It was added to the New South Wales State Heritage Register on 13 August 2010. History Part of the site underwent archaeological excavation in May and June 2006, in advance of the Glasshouse development. Historical research had indicated the presence of a number of previous structures associated with the 1821-32 penal settlement. The excavation was confined to the area of the basement for the new theatre. The excavation concentrated on the Quarters of the Deputy Superintendent of Convicts and two buildings occupied by the Free Overseers. The other two cottages on the original Henrietta, later Elizabeth Street, frontage were to the west of the excavation area or off site to the west. Only a small portion of the allotment to Cottage 1 was within the excavation area. There is no precise date for the construction of the cottages. They are first shown on a map dated to 1824. Additional historical research indicated that the Deputy Superintendent of Convicts and the Free Overseers were appointed in 1823, so it is highly likely that the cottages were built to receive their new occupants in that year. Penal settlement Port Macquarie was one of a number of penal settlements for the secondary punishment of offenders. Convicted criminals were sent to New South Wales from 1788 to the end of transportation in 1840. If they were convicted of additional crimes in New South Wales, they were sent to places of secondary punishment. On the New South Wales coast, Newcastle was the first penal settlement for secondary punishment from 1804 to 1824, followed by Port Macquarie from 1821 to 1832 and Moreton Bay from 1829 to 1838. The purpose of these penal settlements was to remove the convict to a place of isolation from the rest of the free population, to keep them at hard labour, as a deterrent to others. Even with the end of transportation in 1840, Cockatoo Island in Sydney was still planned as a place of secondary punishment in 1839, closing in 1869. Port Macquarie was like most of the other places of secondary punishment, in fact also