Great input Roger, thanks!

I've followed your excellent advice and implemented a tan background, a grey cross-hatch to represent the cobbled section of town, and used the "wood" fill with a dark grey for cobbled streets and with rich brown to create fields ready for planting. I'm using CC2 and don't see a "meadow" or "farmland" fill, but maybe I'm just missing it.

I also used the grass area fill from the city menu along the outside of the castle. It looks good up close, but I don't like how it looks from a distance - too dark. Does anyone know any way of to "thin out" the dust fill in CC that is causing the problem?

Here's the updated map of Middleton.