Sometimes as a passenger as the car travels the rumpled hills of Vermont I look out the window and try to match up topographic features seen from different viewpoints. That hill's peak there, when I'm down in the valley will I be able to see it and which one will it be? From this perspective, where is such-and-such a road or river I know? If I can see that point from here, when I'm down there, what will where I am now look like?
And it's surprisingly hard. We get so used to thinking in terms of the roads, and the way they appear on a flat map, that topographic features aren't nearly as clear to us as we tend to imagine. From up on a high hill, it's easy to not realize how high the spot you're on will look when you look back up; I often find myself imagining I'm coming around the back of a high hill when I'm actually going right over the top, nearly. Features which look important from high places are often all but invisible down in the valleys where we spend most of our time. Heck, I find that without a map to cross-reference, I usually can't even tell if this hill I'm looking at is the same hill as the one I saw from the other side earlier, or the next hill down the range.
I suppose it's possible that I am particularly bad at this, but I suspect it's more likely that all of us who mostly navigate by roads are worse at it than we realize until we try. In fact, I wouldn't be surprised if people who go hiking and mountain-climbing are a lot better at it, but still not as good as they imagine they'd be once they're outside the range of lands they are familiar with. Doing most of your navigation by road tends to make us think in terms of the roads so thoroughly that other landmarks don't get retained.
Of course maps are the great equalizer. When I bother to dig out a map and match up topological features I'm seeing with those on the map, a lot of this uncertainty vanishes instantly. But unless I make a pretty serious effort at it, figuring out the landmarks with a map doesn't stick; the next time I will find it just as tricky as I won't remember which peak or river is which, or being able to identify the same topographic feature from different vantage points.