A Herd of Headless Horsemen, Part I: Sleepy Hollow, Illinois

September 1, 2018 — In our universe, The Legend of Sleepy Hollow is a rural colonial tale set in the gorgeous autumnscape of New York’s Hudson Valley. But in an alternate universe, The Legend of Sleepy Hollow is a midwestern farm story, the Headless Horseman more overalled scarecrow than uniformed soldier. In yet another alternate universe, the legend is a sunbaked western, with a headless cowboy who lassos the craniums of his victims.

I know because I’ve seen the residues from those other two timelines bleed into ours. Seen them with my own eyes. Stepped in their dust with my own boots.

Let’s go on a Headless Horseman hunt. In two parts. Starting with the Land of Lincoln.

The village of Sleepy Hollow, Illinois, is 40 miles northwest of Chicago. Its name is drawn from a single farm that was bought in the early 1950s and then subdivided into an incorporated community (which means it bore the Sleepy Hollow moniker 40 years before the original New York site adopted it). Today some 3,500 Illinoisans have to endure Halloween jokes when mentioning the name of their town. This midwestern Sleepy Hollow is also a completely residential community. No businesses. No main street. No way for the town to really focus its energy on capitalizing on Washington Irving’s brand. But the Horseman is out there.

To call this village Headless-Horseman-themed is going too far, but it’s still true. Every welcome sign bears his silhouette, as do many of the street signs. The local elementary school uses him as a mascot. He’s on the uniform patches of its constabulary. A few lake and street names reference the story and its author. And that’s enough to get me to visit.

The signs are really the only photo-op, though. Unless you get yourself arrested by that aforementioned police force with the cool patches on their shoulders. Which I would totally do if they could promise me it would appear in my mug shot somewhere. Those pleasantly painted wooden signs pop up regularly around the area and are almost flaglike, with the white silhouette of our favorite ghost rider rampant on a field of sunset striped sky and green trees.

Interestingly enough, they have foregone the usual interpretation of the horseman as a hellbent horror for one more true to the spirit of the story. Illinois’s Headless Horseman is almost goofy, with its floppy shirt and arms raised in a children’s book ghost pose and a horse that looks more like its running from something than after something, all of which you can see in more detail in the town seal. This is obviously Bram Bones in a costume and not a demonic soldier-for-hire. Not intimidating at all, but probably enough to scare a skittish pedagogue.

And that’s all I did in this alterna-Sleepy Hollow. Found a sign and got some photographic evidence of this crossroads of the multi-verse.

But I will say that an Illini Sleepy Hollow isn’t too much of a stretch, atmosphere-wise. Despite its “Prairie State” nickname, the state can do some serious Fall. It gave us Ray Bradbury, for goodness’ sake. And, only eight miles away from Sleepy Hollow, is Goebbert’s, a South Barrington garden center with a giant jack-o-lantern atop its silo fit for a giant headless horseman. That reference will pay off in the second half of this article.

Basically, Illinois is a state that the decapitated demon of lore could call home easily. But what about the desert of Wyoming?

Continue to the Sagebrush State...