This Comic's Cast:

This comic would tend to indicate that Darkmoon was just starting off on his path to heroism in this little tale. The timing seems somewhat right for that, since the Old Man is telling the tale from when he was like five or seven or something. I've been rather vague on how old Darkmoon is, but this would seem to line up pretty well.

And yeah, Darkmoon can't find his way out of a paper bag normally, but you could put a tavern in the middle of a labyrinth and Darkmoon will make his way to it as if there wasn't a giant freaking maze in the way.
 
    

When evil spreads across the land, and darkness rises and the monsters roam. When the creatures of the night make beautiful music, and the things that go bump in the night go bump with greater enthusiasm. When the world is in peril and is in need of a hero...

These guys are, sadly, the best the world can hope for. These are the adventures of the heroes of CVRPG. They mean well, they try hard, and occasionally they do the impossible...

They actually do something heroic.