This is a remake of the Brindol city map from the D&D 3rd edition adventure "Red Hand of Doom". It sticks to the old city's general shape for the most part, except that there are now a lot more buildings and streets within the city walls since I found the original layout too small for a city of about 10,000 people. I also tried to make the street layout a bit more organic, with different angles that show how the settlement sort-of crept up on the keep in the city center over the centuries.
There is one version featuring city gate names and street names of my own design (the street names might help coordinating where everyone is when running Red Hand of Doom's climactic battle of Brindol); and a blank version where you can insert your own labels as you see fit.
Source: Red Hand of Doom, Brindol map by Mike Schley
Tools: Adobe Photoshop CS 3, Paint Dot Net, notebook, some pencils stolen from IKEA.
Time: 10+ hours. I revised the first result and fiddled with a lot of details afterwards.
Enjoy!