The later fourteenth century is blessed with sources enabling historians to create portrayals of colourful careers in arms. The testimony of deponents before the Court of Chivalry gives the soldiers' own accounts of their activities, while the portrait of the knight in the Canterbury Tales delivers an image of (allegedly) perfect military accomplishments. To this, we can now add the online database produced during the ‘Soldier in Later Medieval England’ project, which provides evidence of both actual and intended service for the English crown. Combining these sources, we can reconstruct a number of detailed case studies of soldiers and where they chose to fight. We can also test the depositions in the Court of Chivalry against the royal records of military service, and consider if the witnesses were braggards, or, by contrast, were modestly understating their level of military service. Finally, can we find out which soldier was ‘best’: who had the longest record of service; who took part in the most varied campaigns; who was the youngest; who was the oldest; and, of course, as the title suggests, taking the line from the description of Chaucer's Knight, who rode the furthest? This essay is limited to a set of case studies, drawing mainly from cases heard before the Court of Chivalry and expanded with further information from the medieval soldier database. Although they cannot be said to form a truly representative sample of the medieval English soldiery, nevertheless, this self-selected sample does indeed allow us to paint a dynamic portrait of what an average, as well as an exceptional, career in arms could involve in the later fourteenth century.