Well I think that I will call this map done. I started this map with pyrandon's Medieval Town Map tutorial, and went off track a bit I think. It was done in Gimp instead of Photoshop, so some of the techniques described in that tut had to be improvised in Gimp. Most notably the houses. Never did figure out how to apply a bevel to them, nor how to give them some height. I fiddled around to get what I got , but not really satisfied with them. (Also have forgotten just what I did to them exactly). I also had trouble with following the tut where the hill was concerned. Emboss and Bevel layer effects (actually layer effects in general) seems to be the major problem in translating Photoshop into Gimp.
Any way, This is Teston, a rocky outcropping in the middle of a large flood plain. At one point there was a major flooding of the plain due to the distant river (think along the lines of the St. Lawrence) overflowing its banks. The survivors flocked to the nearest high ground and waited out the flood. The flood lasted long enough that permanent structures were created and a village grew out of the refugee camp at the top of the hill. As the waters slowly receded, more buildings were added to the village further down the slope.
Over the years, the area around the village became more wooded as people started to return to the more fertile lands closer to the river. At this time Teston is a minor stopping point along a trading route between the more developed lands further south and the more populated areas to the north. It sits in an area well away from any real enemies, and continues to grow on the trade that passes through. It also has its own trade in lumber and and a hunting/trapping community, and enjoys the peace of being left alone for the ost part.
I actually like the way it turned out, but I wish I could have figured out how to add cliffs to parts of the river banks. The WIP thread is here = http://www.cartographersguild.com/showthread.php?t=4331