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.
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Name:	Eastport Background.jpg 
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Here's the sketch without the background
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Name:	Eastport No Background.jpg 
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Size:	1.87 MB 
ID:	109324

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.