i mean this is all very dependent on time, place, and people. there are people that were fully nomadic at all times of human history. they certainly didn't stay in a town either. some people did travel, clearly. devout religious folk, merchants, well to do young men... there have always been exceptions, but on the whole as a norm, over 500 years ago most people didn't travel much. and more to my point, pilgrims traveling like that likely didn't have maps most of the time. they likely got directions to the next town by the people that lived there.