My Spooky Sleepy Hollow Adventure of Ghoulish Horror

Living in the purgatory between upstate New York and the City has a few advantages, among them proximity to Tarrytown and the legendary hamlet of Sleepy Hollow. I realized recently that I have lived near the renowned village for almost thirty years without stopping by even once, opting instead to spend those decades occupying various malls, DMVs, and other rented spaces. I tell myself that I’m not alone, that surely right now some citizen of Rome is driving past the Coliseum on their way to Chili’s thinking “dang, I’ve just got to block out an afternoon and see what that thing’s all about,” but it’s doubtful.

The decision was made that this October we would remedy the oversight and finally make the trip. After a dangerously rowdy Halloween party (we’re still finishing off those lemon bars!), my wife, myself, and three friends set out for Sleepy Hollow. The drive to Tarrytown requires passage over the Tappan Zee Bridge, a practice more singularly terrifying than a thousand Headless Horsemen. We drove through Tarrytown and into the heart of Sleepy Hollow.

In The Legend of Sleepy Hollow by Washington Irving, a picture is painted of a quaint early American village, replete with bakers’ shoppes, schoolhouses and churchyards. Irving never mentions the Dairy Queen, which I think would have made a smashing locale for his story’s chilling climax. Neither does he mention the 7-11, the Sleepy Hollow Laundromat, the C Town Food Mart, or the dozen or so cafes with names like “The Horseman Diner” and “Ichabod’s Cajun Eatery and Funtime Playtown.” These seem like crucial details to have omitted from the book, as they would have added a certain level of credibility.

We parked behind what I can only assume was a haunted Citgo station and set off into the dark forbidding night, armed only with a flashlight, three cell phones, at least one of each major credit card, high quality winter jackets, and a clear line of sight to the police station and dozens of open businesses. “This is precisely how Ichabod Crane must have felt,” I thought.*

Sleepy Hollow Cemetary is the one location which truly delivers the goods in terms of authentic spookiness. Washington Irving is buried here (another fact curiously absent from his book), and as if that wasn’t enough you can take a walk over “the” footbridge where the horseman pursued Ichabod. Nice touch. But no matter how creepy our surroundings were at this point, nothing could have prepared us for the terror which lie ahead.

Sleepy Hollow seems to be dealing with its legacy of brutality and murder through a strategy of intense capitalization. We discovered this when we wandered onto the grounds of the Sleepy Hollow High School Haunted Hayride. We wouldn’t learn until later that it was a hayride (a ten dollar hayride!), so to us it just looked like a bunch of teenagers in gore masks sitting at picnic tables scratching their thighs.

We walked the length of the hayride thoroughfare past several “scare stations.” Each attraction was painstakingly configured to look like it had been haphazardly slapped together. Or maybe they were just haphazardly slapped together. It’s hard to say. Each station was a bizarre and disturbing mix of traditional spook-house fare and post-modern drivel.

For example, one featured, and I swear I’m not making this up, several skeletons in baseball jerseys with backward caps and du rags sitting at a table as the audio from a “Wassup?” commercial looped on a boombox. Another featured a similarly adorned hip-hop skeleton on a toilet, accompanied by appropriate sound effects. This is just the wrong kind of scary.

I must assume that the students manning these stations would have at least acknowledged our presence were we in the back of a pickup truck and not on foot. Or perhaps their apathy was intended as the creepshow, I just don’t know. But they completely ignored us, dragging on their cigarettes and quietly exchanging sentences beginning with the word “bro.”

At a break in the trail we saw an opening in the perimeter fence and made our move. Before we could clear the exit, we were confronted by a particularly cranky woman in a witch costume (at least I think it was a costume – zing!) who demanded to know who we were and where we came from.

“We came up through the cemetery and walked through” one of us explained quite reasonably.

“You can’t just walk through!” she exclaimed, prompting each of us to look down at our legs and confirm their functionality.

“I could report you, you know.”

A sense of fear o’ertook us. Was this an undercover cop? Security personnel? Or even worse – a psychotic Wiccan who smelled church on us?

“I could report you to the office.”

Dread gave way to elation. This blessed woman worked for the high school, and that meant one of two things: either she thought we were high school students (which if true makes her the most wonderful human being ever birthed – sorry, Oprah), or she is a wretched, troubled woman who has worked at a public school for far too long and actually threatens random strangers with office referral. Either way, this made my night.

We glanced at one another awkwardly and continued walking, leaving our new friend alone to deal with her issues. She did not pursue, and we did not look back.

All in all, I would say that in Sleepy Hollow resides a horror so ghastly, so grim, so freakin’ scary that no book or film can capture its essence. It must be experienced.

Oh, and the 7-11 there has Zero Bars. Those are really hard to find.

*Not really.