I'm going to try and do a proper WIP thread for this map. The map will be in a similar, if not identical, style as my last town map: Here

I usually start by generating a layout that I like with Watabou's Generator. Then I sketched over it where I wanted the walls, roads, and any significant buildings.
Eastport Background.jpg

Here's the sketch without the background
Eastport No Background.jpg

I sketched out the roads in more detail than I usually do since this is going to be a large town/small city with more infrastructure.