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Most of my favorite city names are California cities--Playa Del Rey, Rancho Santa Margarita, Aliso Viejo, Altadena, Rancho Cucamonga, San Luis Obispo, Paso Robles.
Those are some very cold upper Midwest towns on that list. Another interesting name from that part of the world, Mackinaw city MI. One of the most mispronounced places in the USA. Just to the north of there is another town, Sault Sainte Marie Michigan, and Sault Sainte Marie Ontario. Those French and Indian names of the upper Midwest can be a mouthful, and usually only people in MI, WI or MN can pronounce them, as they are the most unique place names in the USA.
The native American city names in Wisconsin take the cake, I think. Could be some folk's least favorite due to difficulty or favorite because they are fun. Oconomowoc, Menomonee Falls, and Ashwaubenon come to mind.
Personally I hate names of places that are somewhat misleading. For instance, if they have "Hill/Mountain/River" in the name and they are NOWHERE near a hill, mountain, or river.
As far as favorites, I really like names like Chattanooga, Albuquerque, Tuscaloosa, Talladega, Orlando, Milwaukee, Chillicothe, and some of the ones Fezzador mentioned.
Truth or Consequences, NM.
Honorable mention to Knockemstiff and Kinnikinnick in Ross County, Ohio. They're merely villages, not cities... but fun names!
Perhaps you were thinking of Phenix City, Alabama?
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