Okay so I tried some different techniques for the roads and decided to just draw a layer with brown roads, drop the transparency a little, and add a slight pillow emboss to it.
I put some detail and flow pattern into the rivers using the smudge tool and then I added the labels.
I am kinda concerned about the map looking too cluttered with all the labels right now. Any opinions on how I can keep the labels (so my players can say "I wanna go to Marthton following the Kingsway") but make them look not so messy?
And I'm still not sure how I'm gonna do the farmlands...