Longest Distance Between Two Short Points (rim, estimate, Alaska, road)

[Des-Lab]

Question. What are two places or roads that are a short linear distance apart (a.k.a "as the crow flies") but are far apart in terms of actual driving distance?

An example would be between the end of the road Hwy 180 at Kings Canyon Park (In Central/Eastern CA).

Hwy 395, which runs mainly between SoCal and Reno via the back side of the Sierra Mountains is the nearest other main road-as measured in nautical/straight line miles. The point in question is not far from the town of Lone Pine. I paced it off via Google Earth to be ≈25 miles from the end of 180 in the mountains.

To actually transit between those two points via shortest practical routing, one would have to backtrack all the way to Fresno and then cross Yosemite via Tioga Pass and back down to 395 at Lee Vining and then return to Lone Pine. This highly circuitous and mountainous route looks impossible to pace off, but just an experienced eyeball estimate of looking at the map suggests that one would need to transit about 300 miles and probably 6-8 hours time to move between those two points that are only 25 miles apart.

Does this make sense? What are some others like it? There is no real reason for this request other than as a curious brain exercise and geography lesson. And I'm not talking about absurd ones like Alaska to Russia. I mean two actual points that are close to each other but to reach one from the other requires hundreds of miles and many hours of travel.

Surely the Rocky Mountain states must have tons of spots like that.

[wpme]

North rim of the Grand Canyon to the south rim.

[wutitiz]

tierra del fuego to Vietnam back when the Bering land bridge was still in existence.

[MckinneyOwnr]

There are places in Brazil that are about 100 miles from Rio de Janeiro, but it will take you 6-7 hours of driving to get there because of all the mountain roads and no direct route there.