The Fallout 1&2 refereces of how that wilderness map works are golden, it was a hassle to get attacked by dogs/preying mantis's every 2 metres (Im with the metric system), but it really felt like you explored the area. Everyday people dont have the knowledge of where the biggest town is, they might know its to the north, but thats it, they know to follow the roads, while 200metres into the forest is a huge ruin which noone ever goes to, cause its not on the road...
You dont have time to go daytripping in that kind of life, theres always something to do or to be done.
What Im trying to point out is that people didnt know what lies around them, they just knew their little village and maybe the next one, but around them in the forest or up the road - no clue.
People of that age had no clue.. Couldnt read maps (when there were any map to be read/I'm talking about the commoners now, not noblemen). There were very little intrest in the outside world - you just didnt have the time/resources to bother with anything other than everyday life.
Would be awesome to have the important cities show on the map as oasis's on a otherwise black map. You know theyre there, just dont know the best route to them.