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That reminds me, as a history teacher a lot of people are confused by Appomattoc Courthouse.
There is a small town in New Hampshire called "Dummer". The larger town next to it, Milan, used to sell t-shirts "The people in Milan might not be smart, but the next town over is Dummer" I never thought much about my town's name until The Simpson's made fun of it. They were visiting NYC and Homer had to pee and a bus drove by, its front sign saying it was headed to Flushing Meadows. He imagined a large field full of toilets. (I actually just live in Flushing, not Flushing Meadows, but same point.)
Kissimmee, FL (pronounced Kiss-IH-mee)