Strange/odd names for towns/places I'll start

Floyd's Knob

I grew up in Indiana and my all time favorite is Floyd's Knob.

Also, it's already been mentioned but it's worth repeating just to honor the hometown of Larry Bird........French Lick.
 
Tenino WA(?). Named for the numbers on a telephone pole in the town; ten - nine - zero.
 
One must be well versed in "Seminole" to pronouce many of Florida's cities...here's just a few to practice with...

Allapattah
Altoona
Apalachicola
Arredondo
Chassahowitzka
Chololoskee
Chumuckla
Estiffanulga
Eucheeanna
Fakahatchee
Grenelefe
Huypoluxo
Immokalee
Istachatta
Istokpoga
Lacoochee
Loxahatchee
Narcoosee
Nokomis
Oscela
Ocheesee
Ocklawaha
Octahatchee
Okeechobee
Okeelanta
Phokee
Panachoochee
Pensacola
Picolata
Poinciana
Sarasota
Seminole
Sopchoppy
Tallahassee
Tuscannoga
Umatilla
Wabasso
Wacahoota
Wahoo
Wakulla
Wannee
Weeki Wachee
Wetumpka
Yulee
 
One must be well versed in "Seminole" to pronouce many of Florida's cities...here's just a few to practice with...

Allapattah
Altoona
Apalachicola
Arredondo
Chassahowitzka
Chololoskee
Chumuckla
Estiffanulga
Eucheeanna
Fakahatchee
Grenelefe
Huypoluxo
Immokalee
Istachatta
Istokpoga
Lacoochee
Loxahatchee
Narcoosee
Nokomis
Oscela
Ocheesee
Ocklawaha
Octahatchee
Okeechobee
Okeelanta
Phokee
Panachoochee
Pensacola
Picolata
Poinciana
Sarasota
Seminole
Sopchoppy
Tallahassee
Tuscannoga
Umatilla
Wabasso
Wacahoota
Wahoo
Wakulla
Wannee
Weeki Wachee
Wetumpka
Yulee

Will Rogers often said he was from Claremore - well, actually Oologah, but "can't nobody but an Indian pronounce that."
 
I use to work with a guy from: Cut and Shoot,Texas
I drove thru Jump,Ohio years ago on my way to a job site.
There is:
Black Betsy,WV
Dolly Sods,WV
A-hole,NC
Scaggsville,MD
Sandy Bottom,MD
Boring,MD
Welcome,MD
Secretary,MD
Bulls Gap,Tn
Hicksville,OH
Bush Knolls,OH
Cherry Valley,OH
fd
 
Not a town but I have to smile every time I cross over the bridge and read the sign for Pee Pee Creek.
 
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