Cityographer from Inkwell Ideas is an automatic city mapping tool for fantasy roleplaying games. Based on the demo video, the images it creates aren’t particularly impressive, but what the output lacks in graphics it makes up for in data.
Cityogrpaher doesn’t just create a map, it creates a detailed city database with each building tied to an individual business. Pointing and clicking on a business will tell the user who works there and what products or services they offer at what prices.
Running on Java, so compatible with Windows, Mac, and Linux, Cityographer is available in a limited free version, as well as a Pro version that will generate larger cities and allow the importing of custom icons for $32.