How do you pronounce these city names?

[Zeffy]

OK, it's time to stump folks.

Tchoupitoulas Street, New Orleans.  No south Louisianans need answer.

Uh...

I'll take Chow-Pit-Too-Las, final answer.

[US81]

Chop-uh-too-lus, emphasis on "too," schwa for the unstressed second and fourth syllables.  As an aside, asking directions in New Orleans used to be a fun experience - east and west were pretty straightforward, but instead of north and south, you heard "lakeside" and "riverside."

[Brandon]

Chop-uh-too-lus, emphasis on "too," schwa for the unstressed second and fourth syllables.  As an aside, asking directions in New Orleans used to be a fun experience - east and west were pretty straightforward, but instead of north and south, you heard "lakeside" and "riverside."

And we have a winner! 

[Rainking75]

I've on occasion heard N.O. locals say "chop-toolas", but I agree correct pronunciation is most certainly chop-pi-too-las.

[bassoon1986]

OK, it's time to stump folks.

Tchoupitoulas Street, New Orleans.  No south Louisianans need answer.

North Louisianians know how to pronounce that stuff too 

[english si]

A few other Massachusetts oddities:

--Our second largest city is Worcester (NOTE: No H.), pronounced WUS-ta by the locals.
--Leicester:  LES-ta
--Leominster:  LEM-ins-ta
--Woburn:  WOO-bun
--Needham:  NEED-um
--Dedham:  DED-um
--Stoneham:  STONE-um
--Stoughton:  STOWT-un
--Peabody:  PEE-buh-dee
--Quincy:  QUIN-zee

Not odd if you are British, except maybe WOO-bun.

Our Leominster is simply LEM-sta

NBC's Premier League promos are making a big deal out of how to pronounce Leicester, given Leicester are a newly promoted team, and one non-Mass Americans struggle with (How to spot an American tourist in London - they are the ones asking "How do you get to Lie-ces-ter Square?". Everyone else can say it roughly correctly, even if Kiwis say 'Lister'!)

'wich' and 'wark' suffixes also are unintuitive, esp to Americans. Never pronounce the 'w' and perhaps shorten the first bit. Southwark is 'Suv-uk' (with a weak 'k' - Londoners don't pronounce strong sounds), Greenwich is 'Gren-ich', but Woolwich is 'Wool-ich'.

For Newark, NJ, it's New-irk.
For Newark, DE, it's New-Arc

For Newark, Nottinghamshire, it's New-uk (with a strong 'k')

[ET21]

3. Detroit - Duh-troy

What

I agree, that is not how you pronounce Detroit lol

[US81]

Regarding the pronunciation of Bexar: I hear about an equal mix of "bear" and a version with a long A vowel sound with a light diphthong "Bay'r" - not quite two syllables.

[busman_49]

Ohio placenames:

Wooster: WOO stir (rhymes with rooster)

Nope.

I grew up in Orrville, which is right next to Wooster.  Think of it as calling someone "wuss," then tacking "ter" on the end.

Incidentally, note the two Rs in Orrville.  It's named for Judge Smith Orr and NOT Orville Redenbacker.  Pronounced ORR-ville, and not "orvul"

[jakeroot]

Yes. CLEE-ell-um. But ell-um is one syllable.

Got it. Drop the "u": "CLEE elm".

Almost. Here's a video that demonstrates the pronunciation (go to 0:11):

[english si]

I grew up in Orrville, which is right next to Wooster.  Think of it as calling someone "wuss," then tacking "ter" on the end.

Were they going for 'Worcester' but with more phonetic spelling that like the original hasn't aged well?

[golden eagle]

Here's a couple more:

Tchoutacabouffa River

Lafourche Parish

[agentsteel53]

Lafourche Parish

if this is anything like Belle Fourche, South Dakota, then it is "la foosh".

[golden eagle]

Lafourche Parish

if this is anything like Belle Fourche, South Dakota, then it is "la foosh".

Yep!

[agentsteel53]

Tchoutacabouffa River

I'll give this one a shot. 

"tchou" as in "Tchoupitoulas"; which is more of a "chaw" than the "choo choo", like a train, as I had surmised. 

"ta" and "ca" are short, schwa-based syllables.

"bou" is like a ghost jumping out at you.  "boo!" - primarily accented syllable, though maybe not as explosively spectral; only a tiny bit more forceful than the first syllable.

"ffa" - is one final schwa.

any good?

[golden eagle]

Choo-ta-ca-buff is how I've always heard it pronounced.

[agentsteel53]

Choo-ta-ca-buff is how I've always heard it pronounced.

so this one is a "choo" and the other one is a "chaw"?  well, color me baffled.  or, rather, since we are apparently in the habit of silencing everything after an "ff"... color me baff.

[vtk]

Ohio placenames:

Wooster: WOO stir (rhymes with rooster)

Nope.

I grew up in Orrville, which is right next to Wooster.  Think of it as calling someone "wuss," then tacking "ter" on the end.

I see. So central Ohioans have been misinformed.  The pronunciation you describe seems like the most natural choice, but somehow Wooster gets thrown in lists of oddly-pronounced placenames.

Also, I'm second-guessing myself on New Albany.  I've heard the Albany in NY is pronounced differently, but I can never remember if ours has an "Al" sound or an "all" sound.

[Buck87]

Monticello -- mon-ti-sell-oh

I learned this one first hand a couple months ago while passing through there. I used the Thomas Jefferson pronunciation of "Monticello" while ordering a pizza, and was corrected by the guy on the phone. He also told me that "mon-ti-hell-hole" was a locally used alternative.

[empirestate]

Yes. CLEE-ell-um. But ell-um is one syllable.

Got it. Drop the "u": "CLEE elm".

Almost. Here's a video that demonstrates the pronunciation (go to 0:11):

Ah, okay. I definitely still hear that as three syllables; that's where you threw me. So what you originally wrote: "CLEE-ell-um" is the way to go!

[Arkansastravelguy]

In NW Arkansas we have a town named Gravette. I'm not sure if it's grav-it or grah-vette like corvette


iPhone

[vtk]

In Columbus we have Alum Creek, and a nearby roadway called Alum Creek Drive.  I'm pretty sure that's pronounced AL-um, like the mineral, but some people say a-LUMM, like the stupid false singular form of "alumni" that people are starting to use.  Just...no.

[busman_49]

Also, I'm second-guessing myself on New Albany.  I've heard the Albany in NY is pronounced differently, but I can never remember if ours has an "Al" sound or an "all" sound.

It has the "all" sound.

Also, while I'm thinking about it...the little burg of Dalton is pronounced with the "Al" sound and not the "all" sound

[DandyDan]

Nobody's said anything for Nebraska yet and while I think most are straightforward, some are not, or different from how other places with the same name are pronounced.
1. Norfolk- actually pronounced nor-FORK.  The city wanted to be Norfork, because it's on the North Fork of the Elkhorn River, but the postal service thought it was a mistake and called it Norfolk.  I hear nor-FOLK, but I believe most of them are people not from Nebraska.
2. Beatrice- Be-AT-riss, not like how you pronounce a person with the name
3. Louisville- Lou-IS-ville, essentially like how it looks, not like how the TV people pronounce the city in Kentucky
4. Plattsmouth- PLATTS-muth
5. Hooper- Hoo-per, with the short oo like in hooker

[national highway 1]

A few from New South Wales:
Wollongong: Woolen-gong
Tuggerah: Tuggra
Leichhardt: Lyke-art
Wee Waa: Wee War
Sydenham: Syden-nm
Ourimbah: Oo-rim-ba
Wagga Wagga: Wogga Wogga or just shortened to 'Wagga'