There are four towns in total in the north which are named as Chivahon, Kentucky, Rye, and Philipia.
These four towns are under three nobles— Rye and Philipia are under Marques Ebonics, Kentucky is under Baron Brown, and Chivahon is under Baron Taylor.
Rye and Philipia are near each other, half a day would be the maximum time to travel from Philipia to Rye on foot, but it would take quarter of the day if on horse.
Kentucky is half a day far from Philipia if on horse and would take a day on foot. On the other hand, Chivahon takes a whole day to get from Philipia on horse while a day and half on foot.
People will have to get through Chivahon first before they could reach Kentucky or any other town further up on north. However, one could go take a detour which would take another day or so.
Hence why people would rather go through inside the town than go around it.