A Herd of Headless Horsemen, Part II: Sleepy Hollow, Wyoming

Start at Part I…in Sleepy Hollow, Illinois

Sleepy Hollow, Wyoming, isn’t a town. It isn’t even a village. It’s one of those things called a “census-designated place,” which means people live in civic sin there. About 1,300 all told, in the case of this particular Sleepy Hollow. It’s less than half a square mile in size and is, like its Illinois counterpart, mostly houses. Although unlike the gently wending, softly tree-lined streets of Sleepy Hollow, Illinois, Sleepy Hollow, Wyoming, is a small, tight suburban intersection of streets under that vast dome of a thing they reverently call the sky out there.

Oh, and water towers. Water towers that are very important to this theme.

I couldn’t find the story of how this place got its name. I’m assuming a fan of the story. But I do know it’s about an hour southwest of Devil’s Tower National Monument. And I know that because that’s where I was coming from when I visited this Sleepy Hollow. That’s right. From one devil to another.

I was prepped for roads named after characters from the Washington Irving story. I was prepped that the town welcome sign resembles a covered bridge (which was not in the original story, but sagely added later in by Disney). I was even prepped for its five-story water tower with a gorgeous orange, yellow, and black harvest scene that isn’t really Sleepy Hollow-themed unless you count the scarecrow in it that resembles one used in Tim Burton’s Sleepy Hollow film. Either way, it works perfectly in a place called Sleepy Hollow.

All of those sites are within a hundred feet of each other, the Water Tower at the end of Brom Street, just around the corner from the welcome sign.

What I wasn’t prepared for, though, was a 100-foot-tall mural of the galloping goblin himself.

Imagine this: You’re driving the dusty roads of the state, exiting Route 51 for Fairview Road. You probably shouldn’t take that exit, but you’d heard about a census-designated place with an obsession with a faceless fiend that mirrors your own. Everything is flat and boiling under a relentless blue sky. The ambiance isn’t quite right for what you’re aiming for. You’re questioning whether you should be expending road time on this side-jaunt.

And then you see it.

A Halloween harbinger.

A giant one.

He’s dressed in black astride a matching black steed. He has no head, but in his upraised hand is a fiery orange jack-o-lantern, aimed squarely at your car. Then you realize that the blue behind him doesn't quite match the blue on the sprawling canvas of sky surrounding you.. The Headless Horseman is on a massive water tower.

Being surprised by this sight is one of the best feelings I’ve had in my entire life. No hyperbole. It was like coming across a pond after hours walking across sand dunes. In all honesty, I’m sorry I just spoiled it for you.

It’s also an image that's completely, unequivocally stolen from Frank Frazetta. That’s right. The famous fantasy illustrator. Apparently, the muralist, a local man named Harvey Jackson, ripped him off, was caught, and mea culpa’d publicly. But nobody made him take the ghost rider off the sky-blue cylinder. Because why would you. It’s just too damn cool. I mean, sure, it's merely there to symbolize a subdivision, but it really references a specific brand of magic that I moved to the northeast to feel every year.

The bummer of it, though, was that this water tower, unlike the one at the end of Brom Street, was really far away. Like, not too far away to get a good look at, but far enough away that it was hard to take photos without a zoom lens. The haze of distance blurred it for the likes of my pathetic camera. And it was on gated private property. Which is probably not enough to keep me from such a wonder, but in this case that gated private property was so flat and exposed that sneaking there was completely out of the question for me.

But I’m jazzed to know that it’s there. I hope herds of cattle or buffalo wander in front of it every once in a while. On my death bed, I will make sure I live one more hour just to reminisce about it. Sleepy Hollow, New York, doesn’t have anything close to this monumental a monument.

In the end, the end of this two-part article I mean, it’s no surprise that there are multiple Sleepy Hollows in this country. It’s a generic enough name, like Greenville and Riverside and Newport. But why these two non-New York places have latched onto their primary literary reference, well, that’s a mystery. Just kidding. That also makes total sense to me. I’d do the same thing if I were the leader of a town named Sleepy Hollow: Worship a headless dude on a horse with a pumpkin, no matter if I was in Illinois or Wyoming or, hell, Hawaii.

But here’s an interesting twist. At the end of Washington Irving’s story, we learn that, if you believe the rumors, Ichabod Crane didn’t disappear into hellfire, but fled New York for “a distant part of the country.” Maybe as distant as Illinois. Maybe as distant as Wyoming. Probably not as distant as Hawaii.

That would make him the Johnny Appleseed of ghost stories. And would further emphasize the fundamental truth that you can’t outrace the Headless Horseman.


Ok, ok, we all know there can be only one legitimate town themed for The Legend of Sleepy Hollow and it’s visage-less villain. Check out all of my visits to Sleepy Hollow, New York.