Well this is bullshit.

My favorite town name in Georgia is Coosawatchie. Pass it on our way to my in-laws' place at Amelia Island in Florida every year and it tickles me every single time I see the sign.
 
Sly is how you pronounce Schley!
ETA: BAHAMA in northern Derm had three plantations back in the day…the BAlls, the HAlls and the MAngums if you ever wondered why it had a Caribbean name….it never did.
 
How do you spell Mississippi:
(My dad always got in trouble with this one)
First “m” comes then comes “i” then “s” he comes twice, then “i” come again and “s” he comes twice more then “ipp” and “i” finish!
That’s how you spell Mississippi!
 
Massachusetts has some tough ones. Kissimmee has been hard for me. Goochland, VA gives pause but is easy enough to pronounce
 
The Texas - Louisiana combo, FTW. Look alike, but don't sound alike.

Nacogdoches - Nah-cah-DOUGH-chiss

Natchitoches - NAH-code-ish

Hell most people mispronounce NOLA: Nawl[schwa]ns (2 syllables only)


NC has its share of tricky ones:

Bahama: bah-HAY-ma

Beaufort - Bo-fert (NC)
Beaufort - Byoo-firt (SC)

Cashiers: KASH-urs

Durham - Durm - 1 syllable.

Mebane - MEB-un

Kure Beach - CURE-ee
 
EyeballKid said:
As a native Floridian, Ocoee is definitely NOT the most difficult place name to pronounce.

Not when you’ve got Okechobee, Micanopy, Kissimmee, Wewahitchka, and so many others.
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I think Micanopy is the trickiest: Mih-cah-NO-pee

We lived in Gainesville for some years before moving to Texas.

Here's a puzzler. The county of Alachua and the town of Alachua are not pronounced the same! My wife worked in public health in the town,

Uh-LA-choo-wah: county

Ah-LA-choo-way: town
 
Duke Mu said:
I think Micanopy is the trickiest: Mih-cah-NO-pee

We lived in Gainesville for some years before moving to Texas.

Here's a puzzler. The county of Alachua and the town of Alachua are not pronounced the same! My wife worked in public health in the town,

Uh-LA-choo-wah: county

Ah-LA-choo-way: town
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I went to high school in Hawthorne, undergrad at UF. Dated a girl from Alachua for a short while.😂
 
Zoo_View said:
High school in Hawthorne?

That’s one dumpy town.
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Indeed.

We moved around FL a lot when I was a kid. My folks were both from the Miami area, we moved to Jax, and eventually they tired of the city life and thought it’d be best to raise a fam in the country. We had a nice house and some acreage, but man that town was a dump.

FTR, Interlachen was worse. 😂

I was in the IB program at Eastside in Gainesville for a couple years, but bailed out for various reasons and ended up graduating from Hawthorne high. Not my best decision in life—definitely shoulda stuck with the IB program.
 
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Driving between NYC and AVL I see the Virginia town of Basye on the signs.

I mispronounces Staunton for a long time.

Anybody know how to pronounce it?

How about between Winston-Salem and Asheville: Dysartsville? Nebo?
 
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