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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.
I live in Oconomowoc and it's always entertaining when asked for my address on the phone with some unsuspecting customer service rep. Ashwaubenon is a good one!
Favorites:
New York City
Chicago
Milwaukee
Tallapoosa (I don't know why I just like it for some reason)
Appaloosa (same as above)
Los Angeles
Roanoke
Boston
Miami
New Orleans
Philadelphia -- probably the most lyrical big-city name in the U.S., IMO
New Orleans
San Francisco
Los Angeles
Savannah
Hilo (HI)
Searchlight (NV)
Needles (CA) -- don't ask me why, I just do
Kahului (HI)
Names I dislike:
Pittsburgh -- it's the pits! (Well, that's what the name says to me, anyway)
Hoboken (NJ) -- sounds like "hobo" or "broken" as in broken down
Ho-ho-kus (NJ) -- sounds like Santa Claus with a coughing fit
Scaggsville (MD) -- sounds too hillbilly
As a general rule, I don't like names that are directionally related to a major city, e.g. West New York, East St. Louis, West Memphis, etc. I do make an exception for West Palm Beach, possibly because it is larger than its namesake.
Even if the names themselves are nice, I don't care for the practice of naming a city after its state. (Double dishonor to Kansas City, MO, which couldn't even get the state right!) I will concede the logic if it is the primary city of its state (e.g. New York City), and doubly so if it's the primary city AND the state capital (e.g. Oklahoma City). But to have some dinky little village be the place that dares to call itself the city of its state (I'm looking at YOU, Maryland City!) is just wrong.
Favorites:
Honolulu, Seattle, Sacramento, San Francisco, Los Angeles, Las Vegas, Phoenix, San Antonio, Memphis, Milwaukee, Chicago, Detroit, Cincinnati, Philadelphia, Providence, Washington, Atlanta, Birmingham, Orlando, Miami.
No strong opinion:
San Jose, San Diego, Denver, Oklahoma City, Kansas City, Louisville, Columbus, Cleveland, Pittsburgh, Buffalo, Hartford, Boston, New York, Baltimore, Richmond, Charlotte, Nashville, New Orleans, Jacksonville, Tampa.
Least Favorites:
Portland, Fresno, Riverside, Salt Lake City, Tucson, Albuquerque, Austin, Houston, Dallas, Tulsa, Saint Louis, Minneapolis, Indianapolis, Grand Rapids, Rochester, Bridgeport, Worcester, Virginia Beach, Raleigh.
Akron, Boise, Flint, and Mobile are worse names than Knoxville IMO and I would add them to your worst names list.
Agree with your favorites, though! I would also add Cincinnati, Las Vegas, Park City, and Phoenix to your best names list.
I agree with Akron, Flint, and Mobile. Boise sounds kinda fun, lol. A previous poster mentioned Hoboken. Now that is worse than all those. Hoboken is pretty bad.
In fact, New Jersey has a lot of cities with bad sounding names:
Absecon
Atco (sounds like a department store)
Colts Neck
Cream Ridge (sounds disgusting)
Dennis
Hazlet
Hoboken
Ho-ho-kus (previous poster mentioned)
Mullica
Marlboro Township
Rumson
Sicklerville (horrible sounding name)
Sea Girt
Trenton
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