This thesis comprises a study of the evolution of human settlement in the hinterland of Marsala, in western Sicily, during the island's period of Roman control. The years between the third century BCE–eighth century CE were a period of frequent and significant change. Paradoxically, they are also a period during which Sicily is comparatively little known. A variety of factors have conspired to minimize scholarly attention on Roman Sicily, and as such, the ways in which the island responded to events in the wider Roman Mediterranean. Among the aims of the Marsala Hinterland Survey—an archaeological survey project active between 2007–2010—was to redress this imbalance. On the basis of ceramic materials collected during surface survey, and analyzed using Geographical Information Systems software, I reconstruct the history of settlement in the area of the survey's activity. This history, I go on to demonstrate, is characterized by an impressive degree of continuity, both in respect of the location and distribution of settlement. I locate the reasons for this continuity, and the moments of its occasional rupture, in the changing relationship between native Sicilian and Roman interests, especially as they relate to the production and shipment of grain throughout the Roman empire.