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Here's the first route. It's gonna lead to a ghost town (I'll get into that when I do the next map) so I tried to make the path leading to it have a weathered and overgrown look to it. Of course though it wouldn't be right if the path back down forced you through tall grass so I made sure there was a clear enough path back down that didn't force you into an encounter like the paths upwards does.
I still don't know if I should just go with "route1, route2, ect" or if I should try and think up names for each route when making them.