Tags
City, Dungeons & Dragons, Fantasy, Labyrinth Lord, OSR, RPG, Urban
From my “Ancient Kings” campaign (now known as the Fisher Kings of Sabre Lake), this is Javelin Hill, the small city that is the centre of one of the character’s holdings.
Javelin Hill
Javelin Hill isn’t a great place for a city – it’s primary water source is the swamp just north of the hill and outside of the city walls. However, it’s the tallest hill in the area, offering a clear view over the forests and swamps nearby. That’s why the fortress was originally built here, but the ancillary structures of a larger town are somewhat overwhelming for the limited infrastructure of the area.
Dyson's Dodecahedron 
I really like when cities end up in places that are not ideal for cities, because they grew up around fortresses that were in places that were ideal for fortresses. They have a realistic feel of gradual development and history. They also tend to be more interesting places than cities that are in ideal locations. Also, real cities often have similar development.
I like how you can see that the structures overspill into the surrounding and lose cohesion as the settlement tapers out.