Chattanooga, TN has B&B Steel Erection Corp, their shirts have a large mobile crane with it’s boom raised at a humorously coincidental angle 
Someone needs to replace the “a” in “parking” with an “o”.
My Mother grew up in Fruitland Idaho, which was pretty funny when I was a kid, but what was even better was that Fruitland is right next to the fine town of “Gayway”. Every time we went to visit my grandparents we always drove right by “Gayway Bowl”, which for some reason the owners painted a bright pink Color.
I was on college campus and was watching an excavation/construction business dig ditches, on this occasion it was to run electrical and computer networking cable to another building. One of their trucks happened to be nearby, with a gaudy decal on the side: “LagCo”
Yes, I am enough of a geek to find that terribly amusing 
I live in Beaverton, Oregon. Just the name makes me laugh.
There are many unfortunate business names around, but the best that I’ve seen is Beaver Acres, an apartment complex. “Yup, we’ve got acres of beavers here”.
There was another one I was going to post, but after reading this long thread, it has vanished from my brain.
Here in Edmonton there is a shop called “Tudor Tack”. You know, for those who need saddles from the Elizabethan era, apparently. Weird.
A few from near where I live:
From the Setting Your Standards Too Low Dept.: Sanitary Bakery.
From the Last Name Doesn’t Go Well With The Product Dept.: Curry Donuts.
From the Doesn’t Sound Dumb Until You Stop And Think About It Dept.: Just Windows & Much Much More. (If you just sell windows, call the store Just Windows. If you sell more than windows, call it Windows & Much Much More. If you combine the two names, you look like a moron.)