Going through some files today, I found some of my older handmade maps- ones I thought I'd lost with a hard drive crash. I'm not a graphics person. I'm continually amazed at the great maps I see in my G+ RPG feed. Some people manage to do amazing freehand stuff and some have created incredibly organic maps using tools like ProFantasy's Campaign Cartographer. Most of mine I've managed with PaintShopPro v5. Often I draw something and then scan it in. Sometimes I draw, scan, work with it, print, draw some more, and then rescan.
The most recent map I have is for a Microscope-crafted fantasy campaign I ran last in 2011. You can see the write up for that here, The Hunts Begin. After the players came up with the world I drew a map up for the first session. I expect I'll go back to this world again in the future.
The second map is older, probably stretching back to the mid-1990's. This is from a large island that crashed out of the sky in the campaign. You can see where I've borrowed elements from TSR's Red Steel for some of the areas.