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I think perhaps quirky is in the eye of the beholder. Quirky can be imitated so often that it can become mundane too. To me, quirky is something that is natural and does not try to be quirky. It just is. And different is not always quirky. Unfortunately, by the time a place earns the reputation of being quirky, it is no longer quirky for that very reason.
That is why I agree with Geography Freak's assessment of quirkiness of some of the towns mentioned here. But others really do sound interesting to me.
In the little town of Higginsville, in northwest Missouri, people love to eat brains, and several little cafes have brains'n'eggs on the breakfast menu. That's pretty quirky.