This article explores how Britain’s changing roadscapes are apprehended by the road-user with reference to my own experience of driving the same route between Scotland and Cornwall over the past quarter-century. My pre-millennial analysis of these journeys (published 2000) is compared with more recent driving-events and deploys the same multi-layered autoethnographic methods I first experimented with then. My central argument is concerned with the ways in which drivers and passengers both respond and contribute to such change vis-a-vis those aspects of their own autobiographies which are entwined with the ‘lifecourse of the road’ (Mikhail Bakhtin). The concept I have devised to account for the ways in which the materiality of the road is entangled with the cognitive and affective passage of the traveller is journeying: i.e. the means by which the individual journey is overlaid, and shaped, not only by previous journeys but also the life-journey of the traveller for whom a familiar route has special meaning. The analysis reveals the extent to which increased traffic and congestion has impacted upon the experience of driving long-distance routes as well as the critical role roadside landmarks (and their disappearance) play in orienting and disorienting the traveller.