So I have posted several maps on this site which are based in my homebrew RPG setting of Demetia. This map project started out as just wanting a regional map I could use for the game I am currently running for my kids. I had an old, hand-drawn map from YEARS ago, but the rivers weren't done right and I needed to change a lot of other things as well.
To give some background on the setting:
Several empires have risen and fallen over the course of the last two thousands years. The last, the human-centric Pargeanon Empire, collapsed around 200 years ago. As their empire began to decay, they withdrew from this valley. The empire had conquered several tribal groups when taking the valley, and as the empire withdrew these groups formed a confederation of baronies ruled by a High King. Between the baronies, which are essentially city-states, are various non-human races, all of which are tribal, and many of which are nomadic. To the east, over the Dragon's Teeth mountains, is the dragonborn nation of Xamel, which formed a policy of isolationism during the rule of the Pargeanon Empire and has not been heard from since. The Xamel army attacked the main outpost guarding the major pass through the Dragon's Teeth and destroyed it. The survivors moved north to establish Hammerfast, and the Trade Road was rebuilt on this new path. Roads are maintained by the barons and the High King, depending on which road is in question.
As to methods, I used Gidde's "Hand Drawn Maps for the Artistically Challenged". I could probably do a hand-drawn map myself, but was looking for something in that style that I could do more quickly. This map was done primarily as a gaming tool, not for the sheer joy of cartography, so I didn't want to spend a long time on it. Of course, my perfectionism set in regardless of that goal, so I ended up putting more work into it in the long run than I had really planned.