Sleepy Hollow and the Joys of Headlessness

From the listless repose of the place, and the peculiar character of its inhabitants … this sequestered glen has long been known by name of Sleepy Hollow … A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere.

— Washington Irving, “The Legend of Sleepy Hollow”

October is here, that most wonderful of months. It’s the most romantic time of the year. The wind in the trees, the early dark, the restless dead.

A chill enters the air. The last harvests are upon us; we must offer a portion of our crops to the Aos Sí, as the barrier between worlds is now at its weakest.

I don’t have crops, so I bought some squash at the grocery store and left it on my porch. It’s starting to smell.

And I still haven’t come up with a decent Halloween costume idea. I do this every *%$#ing year.

But I enjoy the season regardless. I often wonder what started my love affair with Halloween as a kid. Some aspects are obvious—costumes and candy—but which stories captured my imagination?

The Legend of Sleepy Hollow is the first I can remember loving. This seems fitting, as it is one of the oldest American-authored stories to thrive in modern pop culture. It might be our first nationally-popular ghost story.

I discovered the story through the fairly goofy 1949 Disney cartoon adaptation. It was still in regular VCR rotation in elementary schools during the 1980s, dutifully played for students on Halloween each year.

I remember it frightening me. It doesn’t hold up well (I checked out some youtube videos), but I’m still impressed by its fealty to the original ending: the death/disappearance of Ichabod.

That’s bold. I’ll even forgive its decision to soften the visuals by replacing the horseman’s severed head with a pumpkin.

In reading the history of the story, I was surprised to learn that Irving didn’t originate the headless horseman. It was a common specter in stories and legends of northern Europe, an omen of bad fortune. Irving just transplanted one to the Americas and made it corporeal.

I re-read the story itself, too, for the first time since high school. Though wonderfully atmospheric—I’ve always wanted to visit a place of “listless repose”—it barely touches the supernatural. The plot centers on Ichabod’s competition with a colonial-era frat-bro, Bron, for the love of Katrina Van Tassel.

It lacks all the structure and character development we associate with modern stories. There is no redemptive character arc for Ichabod, no positive resolution. The ending is pretty bleak. Katrina rejects Ichabod for Bron, and he dies on the way home when attacked by the Horseman. Yikes.

I’m not surprised that Tim Burton updated the story for his 1999 film Sleepy Hollow. His Ichabod transforms from frightened skeptic to heroic fighter, returning home with Katrina at his side.

So why does this particular story remain popular? The Horseman barely appears, showing up only at the end to deal the killing blow.

The headless horsemen himself isn’t even particularly scary. I think it’s the horse that kills it for me; even spectral horses are cute. I can’t help but imagine the Horseman brushing and grooming his horse, fitting the saddle, attaching a feed bag, and cleaning up poop.

Maybe horses were more frightening in the early 19th century. Death by horse had to be one of the top ways you could die back then. Run over, trampled, kicked, thrown while riding.

Sleepy Hollow endures, I think, because it has so many elements essential to great supernatural horror. The conflict between the modern and the ancient, between reason and superstition. The vulnerability that comes with traveling from modern to rural, from civilization to forest.

Ichabod is a schoolmaster, the symbolic opposite of the rugged settlers exploring the countryside. A true outsider, his job is to bring knowledge, light, civilization to dark places. Yet he is just as fearful of the unknown as the residents of Sleepy Hollow.

What is Blair Witch if not the latest update to the Sleepy Hollow format? City dwellers tramp into woods, armed with knowledge and technology, and discover an old terror.

The gory headless aspect ages well, too. You can’t reason with something that carries its own severed head. If I really stretch, I can see an early foray into body horror, a 19th-century version of Cronenberg.

Last October, I went to a Sleepy Hollow play performed in the forest. It had everything: trees, lanterns, the covered wooden bridge, a galloping horse and Horseman. The play was more comedic than creepy, but just being out in the forest—in the chill of fall, after dark—cast a wonderful spell.

I’ve thought a lot about making a Headless Horseman costume (minus the horse). There are plenty of online tutorials, videos, etc. But it’s a big job, and any suit that requires the illusion of headlessness will not make for a comfortable night.

So let’s raise a goblet of blood to the original American ghost story.