How do I figure out how to get to new locations?

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?

If the destination is your current active quest the clairvoyance spell should give you the best path to your goal. This spell is available pretty early on, try the college at winterhold to purchase it if you don't already have it.

Otherwise it is trial and error or exploring as some of us call it.

In addition to the other very good suggestions (completely forgot about Clairvoyance!), one thing I do is always try to stay at the highest elevation possible. Not only does it give you a better vantage point but it's much easier to descend than ascend; just use Become Ethereal and jump off. You can get it from Ironbind Barrow (great for the Steel Battleaxe of Fiery Soul Trap), Lost Valley Redoubt or Ustengrav (part of the main quest).

Plus you can sprint with Become Ethereal and not drain stamina.

Also the world looks bluer, and who doesn't like blue? Not you, surely.