I used to work groves in a place called Ona FL.

How can I forget:

King of Prussia, Pennsylvania
and
Jim Thorpe, Pennsylvania

North Zulch, pronounced zoolch, central Texas. We turned off our road to investigate what kind of place rejoiced in such a name. It's a little bitty Texas town mostly hidden in the scrub oaks.

Ohiopyle, Pennsylvania. Pronounced exactly as you expect. Never been there. Met a guy in a bar who was from there -- he said it was in beautiful country, but there was no work to be had.

Boring, Maryland.

Ohiopyle is where you can find Falling Water, the Frank Lloyd Wright designed house with the creek/river running through it.

How about Jersey Shore, PA, in north, central PA (nowhere near New Jersey or the ocean)?

In New Jersey, there's Buena, pronouncd Byoona, even though those same people pronounce Lancaster as Lannnn Caster.

These aren't as outright amusing as many already posted, but I get a chuckle out of thinking about the combination of dearth of imagination and practicality in naming the following towns surrounding Westminster, VT:

Westminster West
East Westminster
Had the area grown much we can only imagine the permutations...

When I lived in Quainton in Bucks, we had a matched set of villages close to us too:

Steeple Claydon
East Claydon
Middle Claydon
Botolph Clayden

Although I assume there was a historical reason for this (possibly landed gentry called Claydon) as opposed to a lack of imagination.

We also had a friend that lived in Marsh Gibbon, and although I don't remember any comment on that at the time, we did like Great Horwood (obviously something a lesser whore wouldn't)

Re Vermont, the Dummerstons......North, South, East, West and Center.

RE Alaska, Red Devil, North Pole and my favorite.....Unalaska.

Moose Factory in Canada is another. ;)

and there really is an

Upper Wallop
Middle Wallop
and last but not least
Lower Wallop

Isn't that where all the BDSM types hang out?:P

Used to live just down the 'pike form the dummerstons: Williamsville. aka Bill'sville.

Amazing swimming in those parts.

actually, Dana, I think they mostly commuted from Whippingham, IOW

Pe EllForks (The one *I* always think about when y'all talk about Forks, and a heckuva lot shorter commute). Puyallup Most famous (to me at least) for their fair. They musta got in on the internet thingee early--http://www.thefair.com/ "thefair"? Around here it is The Fair.

Nooksack 'nuff said.

Twisp Whimsical sounding, isn't it? Vader, WA. No link, you can look it up. Named after some guy.

Walla Walla Euphonious, especially when spoken by Roger Rabbit.

Wierd place names was something that I loved as a geography major in college. I remember places like Smackover (corruption of Chemin Covert), Nigger Ben Meadow, and of course, some of the more bizarre Pennsylvania town names like Intercourse, Bird-in-Hand, and Blue Ball.

King of Prussia, incidentally, is named after a what, rather than a who. Because I knew this I won some cool stuff from a local radio DJ ... he used to make fun of the name and would always ask, "Who is the King of Prussia anyway." I called with the explanation that it was named after the Inn that at the time was still standing at the intersection of 202 and Gulph Road (it has since been moved as part of a rescue the historic inn project). He told me I was full of crap and hung up on me. Later that morning, on my way to work, I was quite surprised to hear my call played on the radio! Nearly put my car in the ditch. He made some additional jokes at my expense and played some music. Anyway, shortly after playing my call, he received a call from a very nice lady at the historical society who took him to task for the way he treated me ... a friend of mine told me about this call (we had a no radios rule at work) and I called him back the next morning, told him he owed me, and he apologized, agreed, and sent me a gift pack with all kinds of cool station merchandise.

Wolf the geography major? Wow! Does that help you in your current occupation?
Wolf: "send the men in white coats to pick up Mrs. Smith. She's in Lower Providence, not to be confused with Upper Providence or Nether Providence. That would be Lattitude yadayada, longitude yadayada. Named by Thomas Leper in 1635, it defined the portion of land deeded to Leper by Prince Schlomo, of the Finnish Schlomos - a deed voided by Wiliam Penn....."

Actually I heard recently that it is originally house-ton, and that Houston (hue-ston) was the mutilation. Perhaps it became popular because of Sam Houston or somethin like that?