Only if you make a side trip to Ding Dong, Texas. NOT going to pass THAT up.

i feel like it's only natural that a UMD event of some kind be staged here at some point

I would have gone with Intercourse, PA instead of Coupon, but that's just me.
https://lancasterpa.com/intercourse/

BTW, I have mentioned this before, but once again,
I only live less than 15 miles away from WhyNot.

It's a small town, but they love their name, and sell lots of merch.

Been spending most our lives living in a Catfish Paradise

I like rainwear, so Waterproof sounds promising too. There's a locality in Grimsby, Yorkshire, called Pyewipe which makes me think of somebody slowly pushing two eye holes in a think layer of cream.

Worms, NE I expect is named after the city in Germany, so it's not quite so stupid as the others.

I want to know how Scratch Ankle, Alabama got its name. Or perhaps I don't.

Also, I grew up in Boring, Oregon. I wouldn't say it's the strangest city name in the state. That's probably Drain.