The Funny geographical names thread got me to thinking about place names that are not pronounced the way you’d think they would be.
Near where I live in Southern Illinois, there is the town of VIENNA - pronounced “Vai-ANNA”.
A bit further south of that there is Cairo, IL - pronounced “KAY-ro”.
There is STONEFORT, IL - pronounced “STUN-fut” or “STONE-foot”.
HUEGELY, IL is “HIG-lee”.
PYATTS, IL is pronounced “PITES”.
I still like the recient commercial whereby the teenaged boy mailes a package to Pa-ho-e-nix.
The lady next to him looks at him funny and he says (as only a know it all teenaged boy can) “You know, the capital of Arizona!”
Leicestershire = “lester-shire”
Worcestershire - “wooster-shire”
Belvois - “beever”
Cholmondley = “chumley”
Benwick - “bennick”
Featherstonehaugh = “fanshaw”
Lots like that in the UK 
I live in the Chicago area, where everyone knows who Casimir Pulaski is. We have a street named after him, and many public schools have a day off in his memory. And we all know how to say his name: pull-ass-key.
In Indiana, there’s an entire county called Pulaski, but they pronounce it “pull-ass-sky.”
Then again, try asking a Chicagoan to get you to “paw-lee-nah” street, and they’ll laugh at you, because everyone knows that Paulina is pronounced “paw-LINE-ah.”
There’s a lot of French place names near where I live, so the pronunciations often get botched by the anglophones in the area. For example, Port Mouton (poor mou-tuhn*) is pronounced ‘port ma-toon’.
One which drives my mother crazy…Port L’Hebert. Should be pronounced ‘poor luh-bear*’. Nope, Port Le Herbert.
*If anyone wants to try and correct these feel free, I’m not good at explaining pronunciations
Ashantee - ASH an tee [was originally a shanty at a road crossing, mapper coudnt read the notation correctly]
Avon - A von, not soft a [like ash] von like the english pronunciation
Versailles - ver Sail
That’s a surname, not a place!
Some Ontario street names with unexpected pronunciations…
Annes Street in Whitby: pronounced “Ann-ess”. Interestingly, I think it was orriginally “Anne’s” (the posessive), but somewhere along the way the apostrophe fell off the street signs.
Weber Street in Kitchener-Waterloo: pronounced “Wee-burr”, not “Web-burr”.
Kerr Street in Oakville: pronounced “Kurr”, not “Kairr”.
Eglinton Avenue in Toronto. This one has a longer story. Originally it was pronounced and spelt “Eglington”. However, sonetime in the late nineteenth or early twentieth centuries, it came to be pronounced “Eglinton”, and the street signs were changed to match. Now, I notice that just about everyone pronounces it “Eglington” again. Wonder when the signs will get changed back…
They have a KAY-ro in Georgia, too. And not far from here is Monticello - not like the instrument, but like the plastic wrap.
Hurricane, Utah - pronounced HAIR-uh-cun
Of course there’s Rodeo (“Ro-DAY-oh”) Drive in Beverly Hills, CA.
Waterloo, IA - The locals pronounce it "Water-LOO"
The county seat of Benewah County, Idaho is St. Maries. Please pronounce it Marys .
I’ve been to what I thought was Mary-etta, in Georgia, but everyone there says it more like “May retter.”
Southern New Jersey is home to Forked River, but it’s pronounced For-ked. I believe that’s on the NJ citizenship test 
How else would you pronounce it? 
Also in Illinois, there’s Athens, pronounced “AY-thens,” and New Berlin, pronounced “new BER-lin.”
The name comes from a place near Haltwhistle in Northumberland. 
It means “meadow near the feather shaped stone”.
There’s a few towns called Featherstones left in the UK, and a Featherstone Castle in Haltwhistle (which is where the surname comes from).
Also in Georgia:
Albany- pron. all-benny
Perry- pron. Parry
Cordele- pron. Cor- dee-yull
Off the subject, but a geographic oddity about Georgia is that it has many cities that have the same name as one of its counties, but the city is never IN the county with which it shares a name (e.g. Quitman, Cuthbert, Baldwin, Perry, etc., are never located in Quitman, Cuthbert, Baldwin and Perry counties, which like as not are in different corners of the state.)
When I was little I lived for a year in LaFayette, AL, which is pronounced "lah- FAY’- it (emphasis on second syllable and last syllable almost absent).
There is a city in NE Oklahoma named Miami. Pronounced with a ‘uh’ sound instead of ‘ee’ at the end by the locals.
There is a large village in upstate New York named Pulaski, pronounced much like they do in Indiana: puh-LASS-kigh (that last syllable is “sky” without the S). And in the Great Valley of Virginia is the city of Pulaski, pronounced, p’yew-LASS-key, with a very strong palatalization in the first syllable. I’m not sure how New Jerseyites reference the Pulaski Skyway.
Then there are the various Norfolks, which I never can never keep straight. Some are NOR-f’k, some are NOR-foke, some NOR-folk, some NOR-fauk, and about 150 miles north of Pulaski, NY, is the one commonly referenced as NOR-fork.
44 miles from the Virginia border on I-95 in North Carolina is the city of Rocky Mount, but only natives and folks from Maine ever say its name correctly; the second word is MAOUNT.
Without IPA characters I won’t even try to represent how Chaumont, France, is uttered, but Chaumont, NY, is shuh-MOE. Southeast of it is Lowville, which would rhyme with cow-ville, and which is near the rural hamlet of New Bremen, which sounds like a LOTR ethnic distinction: the Shire-folk vs. the Bree-men.
North Carolina also has Conetoe, which is almost (but not quite) the final syllables of Wapakoneta.