Cityographer is a Kickstarter-funded random city generator/mapping software for role-playing games. You set up the parameters for the city you want to randomly generate using dialogue screens like this:
Cityographer then cranks out randomly generated cities based on your choices that look like this:
Cityographer was successfully Kickstarted back in June 2012. Developer Joe Wetzel is still working on finishing the program but has made a lot of progress. So far, though, I haven’t seen any indication on what the retail price of this will be for those who didn’t participate in the Kickstarter funding.