Creating interesting and realistic medieval cities can be surprisingly difficult. Here are some links and suggestions for making great cities for a D&D/Fantasy Game. I tried to include links to free resources. If anyone has any other good links, please list them below!
Online Generators
The Domesday Book: An online generator that produces a lot of information about the city, including the number of each profession that you would likely find in the city. You can provide a lot of inputs to modify the city, including surrounding area, population and the kingdom it is in. Fun to play around with.
City Generator By CrystalBallSoft: A very numbers heavy City Generator. I wish this could be combined with a vector based random map generator. As it is, it’s a little too dry for me to find that useful or inspiring as I create a random city.
Jobs and Descriptions
What did People do in a Medieval City: A not so pretty, but chock full of great information about the types of professions in a medieval city. Great for fleshing out a city.
Medieval City Map Generator: A city map generator that creates text based maps of a cities, naming various roads and placing various points of interest in different wards of the city.
City Map Generator: I’ve played around with this map generator a bit, and it can create pretty serviceable city maps in a pinch. Thanks to Stargazer’s World for hosting it!
Other Resources
Midkemia – Towns of the Outlands: A free PDF version of an old suppliment by Midkemia Press to encourage people to buy their Cities Suppliment, that provides means to create cities. Include 6 different towns for Fantasy RPGs.
Medieval Society: Notes from a college level course about medieval society. Lots of great information on Medieval life.
Kuunari 
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