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I Went To The Real Sleepy Hollow Town And Learned 7 Surprising Truths About The Spooky Legend

by Gwendolyn Plummer
Gwen is a writer, reader, hockey fan, concert goer, and lunchtime enthusiast.

I love a good scary story.

What’s even cooler is when a scary story is attached to a real place that I can visit, or at least learn a little about.

One of the most famous scary stories attached to a real-life location is “The Legend of Sleepy Hollow.”

The short tale, written by Washington Irving in 1820, tells the eerie happenings of Ichabod Crane’s life and death in the village of Sleepy Hollow in Westchester County, New York.

“The Legend of Sleepy Hollow” is one of the most popular scary stories of all time, and its popularity put the teeny-tiny village of the same name on the map.

But how much of it is actually true, and how much did Washington Irving make up?

I took a trip up to Sleepy Hollow to find out.

Thumbnail Photos: Wikimedia Commons / Chris Kirkman // YouTube / Movieclips // Daniel Kapp for LittleThings

What Is "The Legend Of Sleepy Hollow"?

The Headless Horseman Pursuing Ichabod Crane (1858) by John Quidor

Legendary American author Washington Irving published “The Legend of Sleepy Hollow” in 1820.

If you can’t remember the story, it goes a little something like this:

In the late 1700s, the little village of Sleepy Hollow, New York, was haunted. Quite literally. People far and wide knew the village’s reputation for being the stomping grounds for hundreds of ghosts, the most famous of which is the Headless Horseman.

The tale follows schoolteacher Ichabod Crane, who moves from Connecticut to Sleepy Hollow. While there, he falls in love with a young woman named Katrina Van Tassel, and begins to court her.

Katrina has another suitor, though, a man named Abraham “Brom Bones” Van Brunt.

One night, Katrina rejects Ichabod at a party. Upset, Ichabod gets on his horse and rides home. He rides through Sleepy Hollow, passing some of the village’s most haunted spots. On that spooky ride through the night, Ichabod Crane comes across the infamous Headless Horseman.

The story ends with Ichabod’s mysterious disappearance at the hands of the Headless Horseman, who may or may not have been Brom Bones in disguise.

So, How Much Of It Is Actually True?

So, How Much Of It Is Actually True?
Daniel Kapp for LittleThings

I decided to see what facts I could dig up on this famous story.

I learned that there’s no doubt that “The Legend of Sleepy Hollow” is a work of fiction — but the town does live up to some if its spooky reputation. Here are seven things I learned about Sleepy Hollow that you might not have known.

According To The Movies

According To The Movies

There are two movies that come to mind when I think of Sleepy Hollow: The Disney classic  The Adventures of Ichabod and Mr. Toad and the 1999 Tim Burton Sleepy Hollow.

I remember loving the Tim Burton movie the first time I watched it — it’s a great balance of scary and historical, but it’s actually pretty unfaithful to the original tale. In the movie, Ichabod Crane (played by Johnny Depp) is a detective investigating a series of murders in Sleepy Hollow. Unlike the story, he gets the girl at the end.

Meanwhile, Ichabod and Mr. Toad is a little more of an honest adaptation of Irving’s original story.

1. Sleepy Hollow Wasn't Always There

Welcome To Sleepy Hollow sign

The area where Sleepy Hollow is today was settled by Europeans in the early 1600s, but the town of Sleepy Hollow didn’t actually exist until 1996 — over a 100 years after Washington Irving’s famous tale was published.

As Irving writes it, Sleepy Hollow is an area within Tarrytown — but he totally made it up. Both Tarrytown and Kinderhook, New York, claim to be the actual site of the spooky story.

Still, there was no town in Westchester County actually called “Sleepy Hollow” until 1996. That year, the village of North Tarrytown officially changed its name to Sleepy Hollow. The local school sports teams are also known as “The Horsemen.”

2. The Town's Main Attraction Is A Cemetery

Sleepy Hollow Cemetery
Kat Manos for LittleThings

Sleepy Hollow is just as “sleepy” as its name suggests. There is a cute downtown area, but the main attraction for visitors is Sleepy Hollow Cemetery. This is where I visited on my trip.

It’s hard to describe how truly massive Sleepy Hollow Cemetery is. According to their official website, the cemetery is 85 acres, with over 40,000 graves.

It’s also stunningly beautiful. Those 85 acres are situated on rolling hills overlooking the Hudson River. When I visited in late October, the autumn foliage was beautifully atmospheric.

3. And It's Totally OK To Walk Around

3. And It's Totally OK To Walk Around
Gwendolyn Plummer for LittleThings

Even though Sleepy Hollow Cemetery is a place of rest for the dead and mourning for their loved ones, it’s also a tourist attraction… and apparently, that’s totally OK.

When I stopped by at 3:30 p.m. on a random Sunday, the cemetery was pretty well populated with tourists and cars. There are maps that point out the most famous burial sites on the grounds, including Washington Irving’s.

Sleepy Hollow Cemetery also holds events like walking tours, photography workshops, and even Halloween happenings like Spooky Stories from Six Feet Under and Beyond the Legend: Irving’s Ghost Stories.

4. The Headless Horseman Is Part Of Town History

The Headless Horseman

Washington Irving’s spooky Headless Horseman was supposedly the ghost of a Hessian solider, still wandering the area after the Revolutionary War.

According to Tech Times, Irving got his inspiration from a real local legend probably passed down from the Dutch settlers. Supposedly, they had their own tale of the “Wild Huntsman,” a German ghost who had a penchant for chasing down people lost in the woods.

5. It's Surprisingly Close To New York City

5. It's Surprisingly Close To New York City
Gwendolyn Plummer for LittleThings

Sleepy Hollow is less than an hour north of New York City. It’s an easy train ride from New York’s famous Grand Central Station, or a scenic drive along the Sprain Brook and Taconic State Parkways.

That kind of proximity means it’s really easy to get to New York from Sleepy Hollow, which is part of what makes the village such a big tourist destination.

Despite that closeness, though, Sleepy Hollow feels about as far away from the city as you can get — in a great way.

6. It's Not Cheap

Sleepy Hollow

However, being so close to New York City means living in Sleepy Hollow will cost you a pretty penny.

According to The New York Times, Sleepy Hollow has become a pretty trendy place for young New Yorkers who are just starting a family and getting tired of living in the city.

According to that same report, an average family home in Sleepy Hollow will put you back about $700,000.

7. The Town Embraces Its Spooky History

Sleepy Hollow bumper sticker
Kat Manos for LittleThings

It seems pretty clear to me that Sleepy Hollow loves its spooky history. From adopting the name to calling its sports teams “The Horsemen,” the people of Sleepy Hollow have definitely come to love their local legend. I saw little logos of the Headless Horseman almost everywhere I turned in Sleepy Hollow.

In October, Sleepy Hollow totally transforms into a Halloween paradise embracing the tall tale. It’s a gorgeous little town to visit any time of year, but Sleepy Hollow truly thrives in October.

Gwendolyn Plummer for LittleThings

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