I think I'd use a simple dot for the settlement symbols. Or create a variety of symbols that have layouts that would be recognizable as that particular settlement. As it is, it's pretty obvious that you've used the same group of shapes for each town.
I really like your colors and type. I also like the translucent border—that's a very nice touch that certainly sets this map apart. I think you should experiment with reducing the opacity of the compass as well to match.
I wonder about the four bridges to the north and east of Bird Walker Pass: given that it costs money to build and maintain bridges, why not keep the path to one side of the river? There does not appear to be anything that would warrant more than one bridge just downstream of the confluence southwest of Yope. Or perhaps two upstream of there if the river gets very broad when joined by the tributary. Obviously, there may be a reason that doesn't show up on a map, but it definitely makes me curious.