This chapter opens with a consideration of Jacques Derrida’s intersection of the histories of roads and writing as forms of inscription (tracks, traces, or paths, on the landscape and on the page). These shared cultural histories of roads and writing suggest new ways of conceptualizing the study of the medieval road as material object and as difference: just as the road is the imposition of form on matter, so is writing the imposition of form on nature. In the next section, discussion moves to the question of road nomenclature in medieval Britain. Where ‘road’ serves well enough to denote the universal set of modern commuter routes, medieval terminology is more particularized, more in tune with the contours of the material environment. Some caution is thus necessary in treating medieval roads as a ‘system’. The chapter then argues for a consideration of the medieval road less as a physical entity than as a right of passage: as function rather than physical structure. We then turn to consider how the legacy of Roman roads in medieval Britain and the powerful fiction of the king’s four roads served the social imaginary both in law and literature. In the last section, we offer summaries of the individual book chapters of the volume.