A brief update. I've been a bit busy this week and I've still got another map to do after this one.

When I do maps like these I tend to switch between photoshop and SAI a bit. All my lines are done in SAI (like the sketchy lines on the roofs and stuff). I thought I'd get the chimneys out of the way early. By the way, to do those I just use a 6px line with a stroke and inner glow (normal blend mode, centre, choke 10, size 3 range 17) layer styles. It makes adding them pretty effortless.

The road exiting on the right side leads up to a castle which I've drawn a picture of but no map. It'll be labeled when I get around to doing that after I finish it. Still considering the name.