There’s a Derry and Londonderry in New Hampshire right beside each other. Being from Northern Ireland, that is incredibly amusing to me.
The Phoenicians founded a new city in North Africa and called it ‘New City’ (Qart Hadasht), we now call it Carthage. The Carthaginians founded a new city in Spain and called it ‘New City’ (Qart Hadasht). The Romans conquered both of these cities, and found that having cities with the same confusing so called the second one ‘New New City’ (Carthago Nova).
In Alaska there’s a town called Chicken. They wanted to name it after the Ptarmigan that were abundant in the area, but couldn’t agree on the correct spelling.
Ixonia, Wisconsin solved that problem by just drawing random letters from a hat until they came up with something pronounceable: Ixonia.
But I’m always amused by the street Oxford Place near my house. It’s a street named after a university, named after a city, named after a shallow spot where cattle could cross the river.
In Iowa, we have a Madrid, but its pronounced like MADrid. And a town named Nevada, but pronounced NeVAYda.