In this chapter I address a gap in the study of medieval space, namely that there has been no systematic study by either medievalists or road historians of how European road travellers in the later Middle Ages found their way around: between countries, from one part of a country to another, or within unfamiliar towns and cities. How did travellers plan their journeys? What aids did they use for getting to their destinations? I present some of the evidence for medieval wayfinding, and provide some initial answers to these questions. I consider the use of guides, landmarks, maps, and urban signage, and draws on evidence from English literary texts and English-French phrasebooks. Wayfinding is simultaneously a technology, a memorial practice, and a cognitive competency. I argue that medieval wayfinding is best understood as a form of what Edwin Hutchins calls ‘naturally situated cognition’ or ‘distributed cognition, in that it depends on human co-operation. Moreover, the environment for medieval travellers was divided up into smaller, more manageable pieces and interconnections – what Kevin Lynch describes as paths, edges, districts, nodes and landmarks – that constitute a hierarchy of spatial knowledge that is significantly different from our understanding and negotiation of space today.