Chasing down our fears in Sleepy Hollow, New York

Because not everything about the past is nostalgic…

Here’s how a visit to Sleepy Hollow, New York and the neighboring village of Tarrytown, encouraged us to stop chasing past fears — and to look out for that elusive Headless Horseman instead.

There are some elements that have a tendency to frighten us. They are the things we often don’t want to remember, yet are forced to, during what often feels like our weakest moments. We become distressed, overcome with emotions and thoughts of impending danger and doom. Some of them real. Some merely imagined.

We are consumed with fear — and some of us rather enjoy it. In fact, we seek it out.

For all intents and purposes, I’d call myself a scaredy cat, but I’m also very curious about all the things that go bump in the night. I think part of it stems but my childhood. My grandmother was extremely religious when young, then some time around mid-life, she began dabbling in the occult — before abruptly returning back to the church with a kind of fervor. Her influence over the family was enough to keep me home on one of the most thrilling of days for school-age children — Halloween. 

I did get to dress up for Halloween once or twice. We lived a thousand miles away from my grandmother at the time, and she had no idea. One time, I dressed as a ghostly nun. Another time, a kind (but ugly) witch with bad green makeup that ended up all over the couch when I fell asleep after eating too much candy. Oh! And then there was that one time in middle school when my best friend and I decided to paint our faces. I don’t think that was Halloween though…I also never thought these photos would see the light of day.

I finally got to take part in the school Halloween parade and tried trick-o-treating. Scared witless after only a few blocks, I returned home suspiciously eyeing the candy I received. I was convinced someone had put shards of glass in it. I was too paranoid — even then — for Halloween. Not so much frightened by the supernatural, but convinced that fellow mortals instead were the ones to fear. Makes a lot of sense given a later career choice.

But as I got older, I began to entertain more of the scares, thrills, mysteries, and surprises that came along with the holiday. While the stories of made-up monsters were entertaining, the nostalgic in me, found that the legends and lore of those who once walked the historic places where I’ve been, were more intriguing. More plausible. And this is what lead me to Sleepy Hollow.

Sleepy Hollow, New York is a quiet sleepy village along the Hudson River, not far from Manhattan. Together with the neighboring village of Tarrytown, the area seems magical, having retained much of the history and natural beauty that has always drawn people to it. Originally incorporated as North Tarrytown in the late 19th century, in 1996, the village adopted a translation of the traditional Dutch name that locals were already quite familiar with — Sleepy Hollow.

The idea behind the name change was to attract visitors following the closure of the General Motors plant that once heavily employed and breathed life (and money) into the community. The main source of the town’s economy was dead and this name change was a chance at a new life. A resurrection of sorts, which hung on the coattails of a visiting short-story writer named Washington Irving, whose time spent in the village later inspired the story that would summon up more than just seasonal visitors to the village.

It would call up the very dead. 

In the words of Washington Irving himself, “Some say that the place was bewitched during the early days of the Dutch settlement…the place still continues under the sway of some witching power…subject to trances and visions, and frequently hear music and voices in the air. The whole neighborhood abounds with local tales, haunted spots, and twilight superstitions.” Yup. As you might have guessed. Sleepy Hollow is haunted.

In an article by The Hudson Independent, the Ex­ec­u­tive Di­rec­tor of The His­tor­i­cal So­ci­ety, Inc. of Sleepy Hol­low and neighboring Tarrytown, was quoted as saying, “There have al­ways been ru­mors about ‘spooky peo­ple and spooky hap­pen­ings’ in our two vil­lages. In the 18th and 19th cen­turies, towns­peo­ple were very su­per­sti­tious, and any­one who was dif­fer­ent was con­sid­ered to be a witch.“

In his famously haunting tale The Legend of Sleepy Hollow which recently turned 200 years old, Irving goes into a bit more detail for us. He says “The dominant spirit that haunts this enchanted region is the apparition of a figure on horseback without a head. It is said to be the ghost of a Hessian trooper, whose head had been carried away by a cannonball in some nameless battle during the Revolutionary War…The specter is known, at all the country firesides, by the name of the Headless Horseman of Sleepy Hollow.”

We could take Irvings’s word for it…or we could seek out the Headless Horsemen ourselves.

William Faulkner said it best, “The past is never dead. It’s not even past.” Which means the Headless Horseman should be right where he was last seen…riding swiftly along the grounds of the Old Dutch Church where he was buried in search of his head. Founded in 1685, the church and its yard, house the remains of local common folk and legends, as well as those that inspired the characters in Irving’s story.

From here, it’s easy to wander off onto the grounds of the Sleepy Hollow Cemetery which opened in 1849 with a dramatic landscape of aging trees, rolling hills. and river views. Rightly listed on the New York State and National Registers of historic places, it is the final resting place of notables such as William Rockefeller, Andrew Carnegie, and the man himself — Washington Irving.

Many of you are already familiar with the story. So I’ll give you the short version: 

A lanky, overly suspicious and superstitious school teacher named Ichabod Crane arrives in a new town. Despite being a scaredy cat like me, he indulges in one too many ghost stories around the campfire. He sees a girl he likes at a party. She likes someone else and rebuffs his advances. He sets off on a sad ride home on an even more depressing-looking horse called Gunpowder, who was anything but the fiery substance he was named after, and ends up in the wrong place at the wrong time.

It is rumored that he crossed paths with the headless horseman who gave chase while holding his detached head on his lap. Ichabod is never seen again and the next morning, near the old bridge, they found a saddle trampled in the dirt, Ichabod’s hat, and close behind it…a shattered pumpkin.

While this is the story that brings infamy to the village of Sleepy Hollow, many more hauntings have reportedly taken place here. And because Sleepy Hollow is very much intact and preserved in its original state (albeit aging like the rest of us) it is very easy for us, the living to, as Irving put it, “inhale the witching influence of the air and begin to grow imaginative, to dream dreams, and see apparitions” — and for all variety of the restless undead to find their way back.

Where some places might consider shunning away stories of the past that might spook future visitors, Sleepy Hollow has instead embraced its hair-raising past and has turned it into the event of the year.

In Autumn, during the Halloween season, Sleepy Hollow puts on a spine-tingling show with haunted hayrides in which thrill-seekers follow Ichabod Crane’s attempted escape route, tours and haunts at Gothic mansions, blazing pumpkins — over 7,000 of them to be exact — individually hand-carved by volunteers, farmers markets ripe for the picking, live music, street fairs, 5K & 10K races, costume parades, and of course, a much anticipated appearance by the Headless Horseman. Town officials estimate that 80,000-100,000 people visit Sleepy Hollow during the month of October.

Look, I’ll be the first to admit that, sometimes there is nothing scarier or nightmare-inducing than our own past. There are many things lurking back there that we do not feel nostalgic about. Memories we do not want to entertain even for a moment. The kind that either paralyzes us or sends us running for the hills. Remembrances that bring about anxiety, fear, and pain. A part of our being we wish we could chop off, burn, and bury.

Fear of the past is a funny thing. Whether real or imagined, it very much affects our present and how we proceed into the future. But it isn’t until we’ve carried it around with us for a while, like a ghost on our back, that we realize it actually serves a purpose. Fear is a survival mechanism. It helps keep us safe from danger. When faced with a threat, our bodies undergo certain changes that help us face or run from the threat, thereby increasing our chances of survival. 

Spending time in Sleepy Hollow, I learned one thing. Always look over your shoulder, but don’t ever summon up those wretched parts of the past. Leave them there where they belong. After all, there are plenty of things to spook us as we head into the future. And we can’t be ready to fight or take flight with all that baggage.

I leave Sleepy Hollow with the words of another writer, Author Liam Callanan, echoing in my head: 
“We’re all ghosts. We all carry, inside us, people who came before us.”

Maybe that’s why sometimes….I lose my head.