Here is an animation of how a fantasy map was created. I'm guessing it was all done in Photoshop or Illustrator, and not with a particular map-making software. Still, it's interesting to see how it was built up.
(It's for the Red Aegis RPG on Kickstarter, by the way.)
And here is a great visualisation of a train journey in photos: photo to the left, map on the right.
(andrewducker pointed this out.)