One of the worst offenders has to be Newark, NJ and New York, NY. How confusing is it for an international traveler, especially considering how international the area is! On top of that, a major train station in NYC is New York Penn Station, and a major train station in NJ is Newark Penn Station.

Someone can land at Newark Airport, and have to figure out the difference between going to Newark Penn Station or New York Penn Station, which are in opposite directions from the airport.

It makes more sense if you know that there used to be multiple competing private passenger railroads. Penn Station was the station for the Pennsylvania Railroad. The Pennsylvania Railroad had stops in Newark and in New York. Other railroads had their own stations. Some railroads had shared stations, hence Grand Central, and all of the stations called Union Station.

Of course the PRR hasn't existed in 50 years so maybe it's time to change the name...

> between going to Newark Penn Station or New York Penn Station, which are in opposite directions from the airport.

They're in the same direction from the airport, and the train will stop in Newark Penn on the way to New York Penn. Some people will be confused and try to get off in Newark, although the conductors normally try to announce this really clearly.

Oops, my bad! I was thinking of going from Secaucus station, another big NJ train station, from which they are in opposite directions.

True - it's confusing from there as well!

I’ve seen foreign tourists get off at Newark instead of New York multiple times. I alwaya hoped they figured it out before it’s too late...

What sucks about this one is it's too easy to get a cheap flight to Ontario, CA thinking it was a bargain, not realizing you're not going where you thought you're going...

There's a few stories of people buying tickets to Sydney NS (Nova Scotia Canada), instead of their desired Sydney NSW, and landing much earlier than expected.

Ouch!

And you thought refactoring a code base was hard

There's also three Strawberry, Californias!

Found that out the hard way when I went to meet a fried at the general store in Strawberry, and wound up a few hours away from him.

When you're from Ontario and say you're from Ontario in California, people think they know what you're talking about, but they don't.

At least once a year, something I buy from a US retailer for shipping to Ontario, Canada ends up in Ontario, CA if it transits from a Pacific time zone. It’s rather frustrating to have that extra delay, and I’m sure the shipping depots that service Ontario, CA or these other confusingly named areas don’t appreciate the extra workload...

In a world with easy to disambiguate postal codes, that's kind of sad.

Right, isn’t that the purpose of zip codes?

To be fair most places in North America seem to be named after European places, possibly with a 'new' prefix. So I don't think it's fair to single out Ontario here.

Not in this case: https://en.wikipedia.org/wiki/Ontario#Etymology

However, it'd be fascinating to see some mapping showing in detail where most place names are from in a region.

https://en.wikipedia.org/wiki/List_of_state_and_territory_na... has the states, but it'd be more fun to dive into towns, rivers, mountains, etc...