After years of mocking my choices and chiding me for not thinking ahead, my mother was finally pwned.
For some reason, she and her husband decided to take a trip to Montana. Instead of taking a sensible route through Casper, Wyoming and cutting west across the top half of the state, they decided the best route would be to travel due west through the bottom of the state and then cut north towards Yellowstone on some back road in one of the most desolate and sparsely populated parts of the state.
Having decided this the day they left, they didn't even bother to call ahead and see if there were any motel rooms available anywhere.
Sparse population
major route to Yellowstone
+ height of tourist season
--------------------------
= no available lodging
Not only that, but there's no camping along that route except BLM and state lands, which are unmarked and you need to have something called a "map" to find them in the first place. Rock Springs/Green River was the last destination with motels before Kemmerer, 5 hours away. And they were going to stop in Rock Springs for the night. So four hours later, they call me, begging for help in finding motels since they:
1. Had a map so old it didn't even show half the towns in the state, much less available camping
2. Have no access to the internet on the road
3. Apparently have never heard of 411
After ten minutes of calling every motel within a 100 mile radius (I did say sparse) and finding them all booked, including Little America and the skeeviest dive in Kemmerer, I had the joy of telling them they were completely screwed.
This is where they spent the night:

The Granger city park next to the railroad tracks, which isn't so much a town as it is a spot of dirt next to the railroad tracks.
So, mom. Next time, you should plan ahead. I can't believe you would be so foolish as to put yourself in that position. Honestly, I thought Grandma raised you better. Tsk tsk tsk.