The City of Raglamore
This is an unlabeled version of a map I made a few years back for a campaign. Raglamore is a city in the kingdom of Milendria, a feudal land in the north of my campaign world. Originally little more than a fortified manor-house guarding the only river crossing for 50 leagues, Raglamore grew to a castle, a garrison-town, and finally a bustling trade city over the last three centuries. The old wall was extended from the original fortifications to guard the northern bridge about 150 years ago, and several fortified manors were incorporated into the city's defenses over the last fifty years. The outer walls of the city are a recent addition, built due to the threat of Rothian incursions into the Lowlands of the kingdom. Of note is the utter lack of structures outside the new walls - so fresh is the fear of Rothian horse-raiders in the people's minds.
Done entirely in MS Paint with finishing touches (texturing of roads, walls and water and the shadowing of woods) in Gimp basic.
Nice, I like the suggestion of fields using cross-hatching. In it's unlabelled state it looks more WIP though, I'd like to know more about it :)
Ehh... I have a fully labeled version, but the gamer in me wanted to post an unlabeled copy for whoever might want to use it (non-commercially of course) in their own games or stories.
Although you have some kind of shadow, the overall map looks flat.