I found this on Reddit’s RPG section recently: An “absurdly detailed” town generator at mathemagician.net. Just tell it the size of town you’d like to generate, plug in some racial profile percentages, and it spits out a list of randomly generated details – members of the town guard, citizens (including adventurers and commoners), names of businesses, and more. Each business is given a staff (and in the case of taverns, a list of regular patrons, including the time of day they are likely to be there), and each character gets a one-line summary of their race, class, level, and two character traits.
Some of the business names end up sounding a little weird (and always seem to follow a two-word format), and there doesn’t seem to be a way to view/download all of the data in one piece (rather than clicking every link and saving each page that comes up). But it’s still a lot of fun to play with, and great for making a quick list of citizens to help populate a fantasy town or city.
The Contemporary Quixotist 