Grosse Ile, Michigan. The name is one of many relics of French colonialism in this area, and it means “Big Island.” (And for an island in a river, it’s pretty big alright.) But we don’t speak French any more, and “Gross Eel” is a pretty unappealing name.
Utrecht, Netherlands.
~VOW
Utah has a number of unlovely place names:
[ul]
[li]Tooele (too-EL-uh)[/li][li]La Verkin[/li][li]Panguitch[/li][li]Paragonah (para-GOO-nuh)[/li][/ul]
Utrecht s/b very familiar name for art students in US.
Grimston - Norfolk - UK
Grimethorpe has been mentioned before, it deserves another mention, I know the place well enough and the name fits the place rather well - locals call the place “Grimey”
Scagglethorpe
Wetwang
Dorking
My grandparents lived near some pretty rough ones in the Ozarks. They lived in Horseshoe Bend, which was like whispering the name of Jesus compared to the surrounding towns.
Aside from the aforementioned Bald Knob, you’ve got:
Ash Flat
Flipping (I have a picture outside the Flipping Church of God)
Myron (pronounced locally as Marn)
Bone Town
Moody
Hocomo
Cottbus
Licking
I’ll see your Schenectady (pronounced “Skank-ectady” by the locals 
) and raise you Coxsackie.
I came out of lurkerdom for that?
Little Iowa towns often have names it’s hard to say without scrunching up your face and squinting a little.
Dows. Bode. Fernald. Mingo. Exira. Traer. Moville. Burt. Otho. Spillville. Oelwein. Elkader. Moingona. What Cheer. Zook Spur. Rolfe.
Awesome. My great-gram was from Austria, but I don’t know where, exactly.
So now, as far as I’m concerned, she’s from Fucking Austria. 
Reminds me of a political comment in a longago Gubernatorial race in Mass. One candidate was said to have had 3 Mass. towns named after him: Peabody, Marblehead, and Athol.
In South Africa there is a small town called Hotazell - pronounced “hot as hell”. Aptly named - not a place you would want to spend your summer vacation. Of course, in winter, the opposite applies!
Boogertown Rd. and Gnatty Branch Rd. intersect outside Pigeon Forge, TN
Just found a new one! One of our customers at work is located in Brattleboro, VT. What’s that supposed to mean? Was the town founded by a bunch of spoiled, unruly children?
Dimebox and Cut n Shoot, Texas! 
Conshohocken and Punxsutawney. Both in PA.
I went to junior high in Orcutt. There is just no way to make that sound nice.
Win.
How about Muckanaghederdauhaulia, over in Ireland?
People around here (I live near Conshohocken) don’t usually even bother to try to pronounce the whole thing. Everyone just calls it Conshy (cun-shee).
My RV broke down on Bucksnort Road, somewhere in the unoccupied regions of Georgia. I rather like the name of the road, although the people there were not the friendliest.