I love exploring in Skyrim. There's just nothing like forging a trail through the wilderness and discovering a brand new location, loaded down with treasures, monsters, and surprises.
However, sometimes I need to get somewhere specific. I find it tricky many times to get where I'm trying to go, especially where elevation differences are concerned.
For instance, I need to get to the top of this mountain, where there's a fort. I circle it as best as possible, when I find a path that seems to lead up:

However, it turns into a dead end:

The map is often no help in determining which way I should approach a new destination - elevation is very difficult to judge, and there's usually too little detail between the clouds and the odd perspective to figure out how to climb up to a given location.
Sometimes I luck out and can throw myself off a cliff at a location, but I don't always have this luxury. I realize I could mod/cheat/glitch my way up mountainsides (I include horses in this, for their unnatural ability to climb vertical mountain faces) but I know that Bethesda must have some way of getting to every valid location, and I just have to figure it out. I typically just brute force my way by circling the mountains until I find the "right way up." However, I sometimes find this process frustrating, and it would be really nice if I could narrow the search space, at least somewhat.
Are there any general tips and tricks for orienteering in Skyrim? How should I go about getting to new locations that I've never been to before, especially when elevation is a factor?