Full disclosure, this guy is mostly just there to fill up empty space.
But the real maps I’ve trying to emulate do often have this kind of depiction of human figures — notice how, for example, the Piri Reis Map depicts kings in Spain and West Africa, or how the Catalan Atlas depicts kings all across Asia.
Now, the position of this guy does kind serve to indicate the location of the major overland route in this part of Realmgard, even if it isn’t explicitly depicted on the map. Maps like this usually don’t depict the roads — the closest thing was usually just a list of directions and distances, either by land or sea.
Also, there’s no real symbolic significance to this dude. With the hat, cloak, and stick, he may look little like Odin or Gandalf, or even the traditional iconography associated with the pilgrimage to Santiago de Compostela in honour of St. James.
But, honestly, it’s not even that deep.
The reason hat, cloak, and stick are associated with those the three above things is because they’re just sensible things to have when you’re traveling great distances by foot.