As the road emerges as a site of productive potential in Chaucer's frame narrative, we are encouraged to consider the dynamics of medieval roads and their capacity to mediate structured and smooth space. Counter to the immobility represented by London and Canterbury's city walls (structured space) and the omnidirectional mobility enabled by bodies of water (smooth space), roads perform and participate in directional movement. They carve vectors into the landscape, pointing toward and away from destinations at either end. But as the frame narrative of The Canterbury Tales suggests, focusing exclusively on points of departure and arrival obscures the value of what lies between. The road is both a line of motion and a place that is enabled by and enables human and nonhuman mobilities. When weather, wear and tear, negligence, or vandalism breaks a road, we become painfully aware of that road as a place. With our passage inhibited, we are forced to see the road as ground and not mere conduit. On a medieval roadway, for instance, one would recognize the impact of iron-rimmed cartwheels on the surface, the loosening of gravel after a heavy rain, and the pits dug by vandals like Prior William Bewick, who in response to a request that he repair the pavement outside York's Castelgate Postern, dug pits in the high street. In contemplating alternative ways of moving through broken spaces, one would note, too, tracks stamped into the surrounding grasses or the proximity of local enclosures, avenues that either invite or prohibit continued movement.

Prior to the sixteenth century, when walls and hedges were built to mark private land, alternative means of navigation were relatively easy to come by owing to customary rights of passage. Likening the medieval road to an easement, Sidney and Beatrice Webb write,