None of this bugs me unless there’s a confusing university attached. California and Indiana Universities of Pennsylvania need to honor some prominent alumni or generous donors by renaming themselves. It’s hard enough keeping track of Washington U, U Washington, U Mary Washington, and George Washington U, not to mention all the U of A’s and U of M’s. Pennsylvania is just playing with us.
Mount Pleasant, MI…Flat as a pancake & not especially pleasant.
And you’d think U of SOUTH Florida would be somewhere near the southern part of Florida.
Marathon, NY … Why they never hold marathon races is something I can’t understand.
Mantua, Ohio. The locals pronounce it Man-o-way.
Mt Vernon NY–we saw the name on a highway sign and thought that was the Mt Vernon that folks were saying was a “must visit.” We got back on the freeway. Eventually we did see Mt Vernon after spending time in Williamsburg.
West, Texas, which is actually nowhere near west Texas. 
@Nrdsb4 When that chemical plant blew up they said t wa in West, Texas near Waco…say what?
“Scipio, NY”
Yay!
“Portland, OR (originally kept thinking it should be Portland, Maine)”
Portland, OR was named after Portland, ME.* Back when it was first taking shape as a settlement near the confluence of the Columbia and Willamette rivers, two of the prominent settlers, each seeking to name the place after their native New England cities, flipped a coin to settle the issue. The guy from Portland, Maine won the toss. The losing city was Boston. I presume that Portland, ME was in turn named after Portland, England.
*It’s an occasional Jeopardy clue that Oregon and Maine are the only two states whose respective largest cities have the same name.
Troy, Montana is the town with the lowest elevation in the state. Coincidentally, after 4 years in Troy, NY, I considered that city pretty much the lowest point of NY state, too. Also, they are both located on Route 2. I have been to at least 5 other Troys.
I am one of the few who has been to Endicott College (not in Endicott), Endicott, NY, and Endicott, WA. Both towns are where Route 26 and Route 17 cross.
When my European SIL went on a tour of the Finger Lakes region, she commented on how it was a tour of all of Europe - Ithaca, Geneva, Waterloo, Naples, Scipio, Genoa, Bristol, and added a pilgrimage to Jerusalem.
I just remembered there’s a Palestine, Texas (where the space shuttle crashed).
There’s a Waterloo, Illinois also.
Wisconsin is filled with place names reflecting settler’s origins. I’m not including places more commonly associated with other states or New somethings.
You can go to Denmark, Poland, Belgium, Athens and Berlin, all in the same day if you wish. This mainly from looking at the list at the back of a Rand McNally road atlas.
You also need to be careful and have the correct spelling of your destination. Menomonie is far from Menomonee Falls (watch out for Menomonee, Michigan just over a river from Marinette, WI as well). Sauk City is not Saukville. Kaukauna, Kewaskum, Keshena, Kewaunee- need to listen and be sure of the whole word. With two of them you could be on the wrong large lake in the same region.
Tampa, Florida has a major N-S Nebraska Ave it but on the other side of I-275 and parallel to it is Florida Ave. There’s a Floribraska Ave as well. But no other state names for major roads. I wonder how Nebraska had influence.
Sometimes place modifiers are the name. East River Drive named for the East river, not E. River. Or N Boulevard St- not North Blvd.
You need to listen carefully as well MN residents attending UW-Madison need to realize it’s Lake Monona or the Madison suburb of Monona and not Winona, MN most likely heard.
De Pere, WI is mispronounced as “peer” while another Green Bay suburb is pronounced the French way- it’s Allouez with a silent z. Shawano seems to be Shaw-no, not Sha-wa-no as out of area national weather people have been known to say and other place names are not pronounced at all like you would think.
The city of Mississippi Mills in Ontario, Canada. It is so named because it is located along the Mississippi River…in Ontario!
In Iowa:
West Liberty is southeast of North Liberty.
We spent one spring break in Manhattan Beach, CA and the next in Manhattan NYC. I suggested Manhattan Kansas the next year but the kids said no.
There is this miserable-looking dead end street in a miserable-looking 70’s cookie-cutter suburb in my landlocked, half-desert state. Its name is Mar Vista.
So no vista, and certainly no mar. Someone was being either cheeky or just ignorant.
That’s like Jersey Shore PA, mentioned upthread. It’s in the mountains.
And, hey, how about Greenland? (Of course, unfortunately, that’s getting less ironic by the year.)
Algiers, a part of New Orleans and the only part that is on the “west bank”, meaning the west bank of the Mississippi, which is actually southeast at that part. Tricky!
It’s also a Jeopardy question - which city is on both sides of the Mississippi river? New Orleans (because of Algiers).
There is also a Due West, SC, Denmark SC and Mt Pleasant SC (Charleston) and Paris Mountain