The overarching question under investigation in this thesis is the extent to which the ideals of penal management as espoused by both British and Colonial authorities were implemented in the day to day administration and management of a convict work force. The focus of the examination is the construction of Major Thomas Mitchell’s line of road between Mt. Victoria and Bathurst in the 1830’s. Specifically the thesis documents the various sites on the line of road with a particular emphasis on the administrative centre and principal facility, No. 2 Stockade Cox’s River, to explain the dynamic interaction of the network and its role in the penal repertoire of New South Wales. In bringing together a large range of sources the thesis has enabled the first thorough reading of the convict sites associated with the Western road. This has led to a multi-dimensional understanding of the place, its people, and the process of its construction. It provides a basis for future scholarship on this neglected network, located almost at the doorstep of greater Sydney, on the western fringe of the Blue Mountains. / Doctor of Philosophy (PhD)