I think this is pretty cool, and I hope you do too...
Random City Map Generator
I think this is a good first cut, but of course there are many things I want to add to it...
A second or third street layout (which are less planned), some extra distinctive buildings (an arena, wizard's tower, etc.), occasional wells, and some other odds and ends.
But you all have more expertise than I do. I'm more of a programmer than an artist or medieval historian. What do you think?