In school, we used to have "wiki races" when we were bored (I later googled this and we were far from the only ones). Pick a start and end article and race to see who got there first, verification via the back button on your browser. For speed purposes, it was usually easiest to just bubble up to the biggest unit of geography in common and then narrow back down.

In college we made a site that represented each wikipedia page as a graph, with sections and links serving as nodes and leafs. It was a pretty fun visualization but we fell short of our ill-defined goal to page rank Wikipedia.

This is pretty neat! And it reinforces my belief that bubbling up is the way to go. In the example it gave me, only a few of the 35 paths didn't immediately jump to a very general concept. One of those was "leet" though :)