Hi everyone. I'm currently working on a D&D campaign using D&D4E and this is my first town map create for the campaign: Wintervale. For the terrain, I used tileable textures with cloud effect layered on top of it. For the buildings and objects, I used mainly MapTool's mapping objects (link) and some others found on the internet, and applied a black outer glow to them to mimic occlusion.
I tried to think of how the town people may live their daily lives there, then proceeded to layout the necessary buildings. Since Wintervale is pretty small for a town (more like a village), I'm in the process of developing he areas around Wintervale and its backstory fitting for the campaign. As for the town map, I believe it's pretty much done at the moment. Those interested in the campaign's continent map, here's the link.
Hope you will enjoy it.