Chillicothe, Ohio gets my vote. The town sucks every bit as bad as the name suggests and then some.
Uwchlan, PA. Try to guess how that’s pronounced by the locals. YOU-clunWelsh immigrants in the 19th century left a ton of Welsh place names in their wake in this area, and a lot of them are cacophonous and can instantly peg you as an outsider when you mangle them, but Uwchlan takes the cake.
I love that Walla Walla is in Walla Walla County, so it’s Walla Walla, Walla Walla County, Washington. 
Never cared for the names of a lot of Alaskan towns. Koyakuk, Kaktovek, Kwigillingok…
They tend to sound like a cat with a bad hairball. 
Cudahay, California
Weed Patch, California
Both make Oxnard look good.
Maidenhead, UK
Leatherhead, UK
Scunthorpe, UK
Mamaroneck, NY
Throgs Neck, NY
Billerica, MA
Wow…50 posts later and the thread isn’t over.
Many of these names are of pretty obscure, off the beaten path names. Scranton, a good sized but not huge city, has a name that is hard to beat for plain ugliness. Also, Yonkers is not the most euphonious of appellations.
Dude, it was a joke.
You just vbarely beat me to it. Among cities that are actually well known, Scranton is surely the North American winner. (It’d be unfair to cite examples from a place like the Czech Republic, where every name is ugly to an English speaker.)
But if we can go worldwide for a moment, I think the world’s ugliest sounding capital city has to be Prague, doesn’t it? “Prague” sounds like a skin infection that a doctor has to prescribe antibiotics to get rid of.
Bothell, WA
For street names you cannot beat Redneck Avenue, which runs between Moonachie and Little Ferry, NJ. Try convincing anyone that you live on Redneck Avenue.
Heard someone once try to fancy this up by pronouncing it “bill-AIR-icka” (it’s actually bill-RICK-a" This was the same person who asked me how to get to "Fellini’s (Filene’s) Basement.
Poultry Lane
Big Bone Lick Ky.
Right next door are Beaver Lick and Rabbit Hash.
Fishkill New York
Pedantically, Prague is only the English spelling/pronunciation. It’s Praha in Czech. Which is a lot nicer. The Netherlands’ The Hague/Den Haag has no such excuse.
My nominations:
Goole, Hull, Scunthorpe and Grimsby around the Humber in the UK.
There’s a load around the Mersey estuary that are rendered even worse when you hear the locals say it: Widnes, Toxteth, Huyton, Birkenhead
I will add Shartlesville, PA, off of I-78. All I can think of when I drive by is sharting.
How about the ugliest street intersection?
My nomination: the corner of Stieglmeyer Street and Blick Street in Buffalo, followed by Kosciuszko Street and Stanislaus Street a couple of miles to the west.