Sleepy Hollow, NY, Part I: You Can’t Reason With a Headless Man

September 23, 2008 — Autumn might not start until the end of September, and Halloween might not fall until a month later, but on my own personal not-sanctioned-by-Julius-Caesar calendar, they both start on September 1st. Sometimes the season enters on witches’ brooms, sometimes on hay wagons, and sometimes on the epic swing of a grim reaper scythe. Other times I have to put it off because of lingering August heat waves. But more often than not, the season is borne on the broad, uninterrupted shoulders of a headless rider with a flaming jack-o-lantern.

And I can thank Washington Irving for that.

In 1820, he published his short story The Legend of Sleepy Hollow, in which a trepidatious teacher in a small New York village encounters the area’s local ghostie, a headless Revolutionary War-era soldier that rides about on a black charger looking for the head he lost to a cannonball…or, barring that, whomever’s has the same hat size as he.

With its harvest-time celebrations, seasonal Hudson Valley scenery descriptions, and ghostly gallivantings, it has become one of the foundational texts of Autumn, and therefore automatically one of my favorite stories. I guess more important than that, though, it’s also become revered classic literature by one of the original American voices. And, of course, as with any other important piece of literature, I was introduced to it through the ever-faithful medium of television.

Disney’s 1949 cartoon adaptation of the story is one of those bits of my childhood that I’m happy to permanently allocate space on the shrinking swampland that is the real estate of my memories. It’s a favorite cartoon of mine (and I state that with the full realization of what that information implies), and not just because of its source material. The animators and storytellers managed to adapt the piece masterfully, accurately, and visually embellished to a point where it often outdoes the original story in places.

In fact, these days, for me to give a fair read to the original text, I have to make a conscious effort to banish both Disney’s animated tracings and Bing Crosby’s accompanying songs and narration from the burnt-out landscape of my imagination. But I will always hear that hellish laughter. In the dark. In my soul. Damned Disney. For those of you who like your pop culture references more R-rated, the 1999 Tim Burton film adaptation of the tale is exquisitely filmed as well, if horribly plotted and dialogue’d, but it’s still worthy supporting material for Irving’s opus.

I wish I could delve deeper than just two paragraphs into the story and its adaptations, but I’ve got a whole town to write about.

Irving set his tale of a headless Hessian in a small Dutch-settled area on the eastern side of the Hudson River Valley region of the state of New York, about 30 miles north of Manhattan near the Tappan Zee bridge. And when I say set, I don’t mean randomly picked a locale on a map or made one up in his head. Irving was in love with that part of New York. He eventually moved, lived, and died there. I’ll be covering the artifacts left over from said life arc in the second half of this article.

As a result of his affinity for the region, he was able to incorporate the geography, history, and landmarks of the area directly into the story, making them conveniently traceable to the delight of future generations of his appreciators as well as the local tourism board. Apparently, though, Sleepy Hollow wasn’t a real town until about a decade or so ago. From what I can tell after a few random Internet sites worth of research, the name Sleepy Hollow either kind of just floated around the valley randomly or was made up by Irving until a place called North Tarrytown, which abuts Siamesedly the Tarrytown mentioned in the story and contains many of the landmarks from the story, officially incorporated itself under the mantle.

There’s more to the chronology, but it’s all a little bit confusing, honestly, and really the only important thing to take away from all of it is that Sleepy Hollow is no longer just an imaginary fiend-haunt concocted by a colonial’s now a location officially recognized by the meticulous records of the U.S. Census Bureau. And that means it’s visitalb...visittibb...visilba...that means you can visit it.

And you’re free to visit Sleepy Hollow in any season you want, of course, buy I highly recommend the Fall time, the closer to Halloween the better. You see, the town knows what side its pumpkin bread is pumpkin-buttered, and they play up their unique ties to the season in appropriate fashion. They spook out the town with decorations, throw a Halloween parade as far as they can, and conduct many Headless Horseman-themed events and tours.

No matter what time of year you visit, though, it won’t take you long to figure out that this is the land of the Galloping Hessian of the Hollow. The mascot of their local school system is a headless horseman, an impressive steel statue stands tall in the middle of the town, various signs mark locations of interest, and local shops carry the requisite amount of Headless Horseman merchandise.

The first thing you see when you enter the town of Sleepy Hollow is, well, the sign that says that you’re entering the town of Sleepy Hollow. I know that sounds like I’m being smug, but I sincerely think it’s worth mentioning. It’s a pretty sign, and it's only been a photo opportunity, remember, since the town renamed itself in 1996.

As for the town itself, it’s small, but well-peopled, being a suburb of New York City, but it for the most part manages to avoid appearing too much like it’s a suburb of New York City. Route 9, also known as North Broadway, cuts through the town, and pretty much everything Headless Horseman-related that you want to see is located on this road. In fact, I think everything Headless Horseman-related that you want to see is, but I always throw in “pretty much” to protect myself. In fights, too.

Anyway, one of those items of interest includes a favorite statue of mine. I know that’s my third use of the word favorite in this article so far, but what can I say? I dig the town, and the story that makes it worth visiting. In fact, I’m pretty sure I’m using favorite more times in this two-parter. Just down North Broadway stands an 18-foot-tall, oxidized steel testament to Irving’s story that takes a bit of creative description to justly convey it in words.

Let’s see...Try imagining a giant corroded carrot...and then stop imagining silly things and just look at the accompanying pictures. At the top of a hollow quadrilateral column are 20 fancifully sculpted oxidized metal plates that overlap to depict Ichabod Crane, whom somehow I have neglected to mention by name until this moment in the article, being chased down by our jack-o-lantern-wielding Galloping Hessian. As unromantic as it sounds, instead of it being the unified, burnished vision of a single artist toiling with art-wounded hands and brain, this piece of artwork was created by a high-end custom metal-working company called, as improbable as it seem, Milgo/Bufkin.

I think it works, though. The unique effect of the stylized plates makes the image look like it’s made of smoke or gnarled tree branches or skeleton bones or other eerie things. All in all, I like it much more than I should like the product of corporate metal art fabrication.

Moving on down the road in the direction that Ichabod is riding for his life, you’ll come across a little church, the Old Dutch Church by name, that was built in 1685 and was featured in Irving’s story as demarcating the domain of the Headless Horseman. It was also around about here that the climactic scene of the story takes place. In the Fall, the church presents dramatic readings of Irving’s story, complete with hot cider and autumn snacks for the audience. Some moments in life should be crystallized into giant jawbreakers and sucked on forever.

If you’re familiar with the story (even if it’s just through that one adaptation starring Jeff Goldblum, Dick Butkus, and Gary not kidding), then you’re probably wondering, “So if this is the church, then where is the bridge?” And I hope that you’re wondering it to the deep cadences of, “If this is a consulate ship, then where is the ambassador?” I wish it was still cool to make those kind of references. Well, if you’ve arrived at the church by taking Route 9 from the south, past our enstatuated hero of the perpetual pursuit...then you crossed right over it.

The original bridge “famous in goblin story” that spanned the stream here beside the church, and which Disney sagely interpreted as a covered bridge, is no longer standing. However, a more modern bridge has replaced it in the original location...because the stream’s still there. These days, you barely notice that it’s a bridge, though. It’s one of those concrete bits of paved road that “ices before road” in winter. It’s now called the Sleepy Hollow Bridge, and, according to an affixed plaque, is dedicated to the author to whom the town owes its tourist dollars. A blue and yellow sign identifies and commemorates the location as the spot of the original “Headless Horseman Bridge.”

You’ve probably put this together yourself already, but you can actually trace the self-acclaimed legend’s entire chase scene to this bridge and church, where it ends in a pile of pumpkin shards and an empty hat.

The chase route starts at Patriot’s Park, a pleasant area along Route 9 south of the Old Dutch Church. Here you’ll find a statue called the Captors’ Monument that commemorates the spot where a British Spy named Major Andre, who was in cahoots with Benedict Arnold, found himself captured. In the Irving story, it was here (long before the statue was erected, of course—back then it was just a tree) that Ichabod first sees the headless spectre, “huge, misshapen and towering.” From this statue just follow along (i.e., run like the horse’d Devil’s on your heels) North Broadway/Route 9 past the Sleepy Hollow statue and on to the supposed safety of the bridge and church where the Horseman There-Can-Be-Only-One’d old Ichabod.

Continue to Part II, which mostly covers the remarkable gothic cemetery behind the church, and the grave and home of the author of the story (which are two different things, despite my phrasing).


  1. While it wasn't durring the fall, I finally got a chance to get to Sleepy Hollow and thanks to your blog, I feel I really got the most out of the experience. Thanks.

  2. Awesome. Way glad to have helped. Sleepy Hollow is still one of my favorite towns on the planet...