Searching for the Headless Horseman

Every culture has its monsters: the Slavs have the witch Baba Yaga who flies around forests with a pestle in hand, Amazonian tribes say sea creatures with supernatural powers swim in the river, and the Jews of Prague have the golem, a monster made out of clay and brought to life in the late-16th century to help protect them from anti-Semitic attacks. Of course, people move, cultures expand to different cities, countries, and continents, and the myths twist and grow. The monsters take on characteristics of their new homeland and eventually you go from the golem to Frankenstein’s monster.

In America, our most famous monsters tend to be more recent Hollywood creations who wield instruments of destruction, like Jason with his machete or Leatherface with his chainsaw. There are local myths and legends of Jersey Devils, the Mothman of Point Pleasant, and various UFOs, haunted houses, and regional spirits that go bump in the night, but American evil tends toward psychopathy tinged with otherworldly powers (think Freddy Krueger, a child molester serial killer who is killed but continues to murder through dreams).

Washington Irving, under the pseudonym Geoffrey Crayon, gave America one of its earliest monsters in his 1820 short story “The Legend of Sleepy Hollow.” Although the Headless Horseman doesn’t show up until the very end, he has nonetheless become a part of our culture. Children know about the Horseman chasing Ichabod Crane on horseback, and the story has been used through the years, most recently in the Fox TV drama, Sleepy Hollow. When you take a ride up to the quaint village of Sleep Hollow in Westchester County — a short trip from New York City — the locals have no problem celebrating their tie to Irving’s famous story. Yet the Horseman, maybe not too surprisingly, is not American in either his own background or the story itself.

The Headless Horseman may have become one of America’s oldest ghosts, but his story was born in Europe and variations of him have long existed in Irish and German folklore. Even in Irving’s story, he is a Hessian soldier whose head is taken clean off during the Revolutionary War, leaving him to rides around at night in search of it. We’ve taken a monster that is foreign in all regards and we’ve kept telling his story for over 200 years.

I took my trip up to Sleepy Hollow on a Sunday morning. Early enough to beat the traffic, I made it there in a shorter amount of time than Google Maps had predicted it would take. I beat the crowds that flock to the area throughout most of October to take the Sleepy Hollow Cemetery tours, or to see the Great Jack O’Lantern Blaze. It could be said that no city in America does Halloween quite like Sleepy Hollow. It’s a place that doesn’t necessarily look like it depends on the Season of the Witch tourist dollars, but it embraces the tag as a famously haunted city nonetheless.

To prepare for my trek, I read Irving’s famous story, collected along with some of his most famous works in a new Penguin Classics edition with a foreword by Irving expert Elizabeth L. Bradley, who supplies some interesting insight into Irving’s infamous villain. Bradley points out that the Horseman “has a touch of kitsch,” which is something that we’ve maybe lost in our contemporary obsession with blood and gore. I was pretty familiar with the story after reading it in high school English, as well as watching not just the 1949 Disney cartoon version narrated by Bing Crosby (my own introduction to the story, by way of a VHS tape rented for me when I was 4-years-old), and a YouTube version of the 1980 made-for-television version starring Jeff Goldblum as Ichabod and football star Dick Butkus as Brahm Bones, but also the episode of Are You Afraid of the Dark? based off the story, the 1999 Tim Burton version with Christopher Walken as the Horseman, and by playing a villager with no lines in my high school’s stage adaptation. I don’t consider myself an expert, but I’ve seen my share of Headless Horsemen.

What I realized as I made my way through the Old Dutch Cemetery, looking at the 18th century tombstones the Horseman was said to tie his horse to at night, was how much the story has evolved over time. There’s hardly any of the kitsch factor Bradley alluded to (far more noticeable in the now-rare Disney cartoon) in the snobby and elitist schoolmaster Ichabod Crane’s reaction to New York bumpkins. They were simple people who could really care less about education, and just wanted to go about their lives in peace. Crane, meanwhile, is fixated on the daughter of a wealthy farmer, which leads to his eventual undoing — whether by malice or exile. Gossip or not, Irving tells us that, “an old farmer, who had been down to New York on a visit several years after,” came back and told everybody that he’d seen the teacher alive and in the flesh. Of course, Irving points out in the last paragraph that, “The old country wives, however, who are the best judges of these matters, maintain to this day, that Ichabod was spirited away by supernatural means.”

There’s a bridge in Sleepy Hollow that’s supposed to be the one Ichabod believed he needed to cross to get away from the horseman, only to find that his hunter can actually get over it after all. The village installed one over a creek that, while not the original, makes it easy to put oneself in the character’s riding boots even today. It’s walking over that bridge where you can not only contemplate Ichabod’s fate, but also wonder if “The Legend of Sleepy Hollow” is a story about a German ghost and one particularly famous victim, or if it’s simply a tale of a of brainless jerk playing a prank on the smartypants from Connecticut. Ichabod’s body is never found, and the only other person who actually saw the ghost of the soldier, Brahm Bones, also happens to be chasing after the hand of the same girl as Crane. As he’s making his horse gallop faster through the graveyard, Ichabod Crane is trying to get away from a haunting — either of the ghost or his own inadequacy.

Irving’s vagueness is exactly what makes “The Legend of Sleepy Hollow” endure. Irving was smart enough to leave what exactly happened to Ichabod that fateful night unclear, and that is the opposite of contemporary horror, which is so fixated on seeing the deed and its bloody aftermath. With the Headless Horseman, we’re not entirely sure what happened, let alone if there ever was a haunting in the first place. Maybe he was just a lone rider mistaken for a phantom in the dark; but in Irving’s story — one of America’s truly great stories, passed on through time — he’s whatever we want him to be.