Gadling infiltrates Southwest HQ for Halloween

As I’m sitting on WN1540 headed towards Saint Louis, I’m starting to realize just how serious they take Halloween at Southwest Airlines. Sure, I know they’ve always been a little wacky – their blog is called “Nuts about Southwest” after all – but I guess at the core of that fun, outer shell I just expected to see the same old straight-laced corporate abomination.

It took me until about page 12 of “Spirit,” their in-flight magazine, to start to change my mind. On it is the normal letter that Gary Kelly, Southwest’s CEO always writes to the reader and passenger — only the topic of this note is how passionate he and his airline are about Halloween. And at the bottom is a cutout picture of Mr. Kelly dressed up as Gene Simmons from Kiss.

Alright. So maybe when I was invited out to Southwest’s headquarters to help judge the annual Halloween contest I underestimated how strange this could get. Yes, they did ask me to dress up and yes, I do have an orange pilot’s suit in my carry-on. But Gene Simmons? Are you serious?

Well, I guess we’ll see what happens. Throughout the day today I’ll be wandering around Southwest headquarters with Gary, some friends from Jaunted and The Cranky Flier, inspecting some of the decorations and skits that the various departments have prepared and declaring the most outrageous getup as winners.

You can follow along at our Twitter feed with live picture updates, or for those more patient among you, you can probably wait until I return home for the closing post. I have a feeling I’ll be sleeping on the return flights.