Spooky bridge

It is said that in 1776, at the Battle of the White Plains during the American Revolutionary War, a Hessian soldier on horseback, fighting for the British, had his head blown clear off by a cannonball. Imagine it, a bowling ball of iron crashing through your skull. You’ve seen watermelon get smashed with a sledgehammer right? Same thing really.

And while on most days this wouldn’t really be polite conversation, this is The Lady Dicks, where we indulge our dark side a little bit and talk about a few gruesome and gory stories. And of those stories, few are as iconic as the story of the Headless Horseman from the Legend of Sleepy Hollow

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The early life of Washington Irving

Washington Irving was born in Manhattan, New York City in 1780, and was one of eight surviving children of Sarah and her husband, William Irving, Sr., a successful merchant.

A sickly boy at times, Washington was sent out of Manhattan at 18 to escape an outbreak of yellow fever. During that time he stayed with a family friend in a little town just north of New York called Tarrytown. Just north of it was another hamlet founded by Dutch settlers locally known as Sleepy Hollow. Even then, tales of its ghostly inhabitants were common and Irving, who was a budding writer at this time, was keenly interested in learning about the local folklore.

After the outbreak, Irving return to New York and started trying to make a career out of his writing.  At first his political commentaries were the first to gain him some notoriety. He published “letters to the editor” and satirical articles lampooning prominent New York politicians and businessmen.  He was also the first to give New York its now famous nickname “Gotham” which in old English means the “home of goats.”

By 1815, however, his family’s merchant business was in trouble and he was sent to England to try and bring it back to life. He wasn’t successful, but following the business’ bankruptcy Irving decided to stay in Europe and continue writing. There he met many famous British authors, including Walter Scott, who encouraged him to write stories and introduced him to British high society. Irving quickly became one of the most popular literary guests at parties held not just in Britain but throughout Europe.

In 1819, while still living in England he published a series of short stories called The Sketch Book of Geoffrey Crayon, Gent. It was well received in England and Europe generally, and Irving was hailed at the time as one of the first respected authors to come out the newly born United States of America. Several of the short stories in that the Sketch Book have stood the test of time and are popular to this day, including Rip Van Winkle and The Legend of Sleepy Hollow.

Headless horsemen around the world

While we can’t be sure what exactly inspired Irving to create the character of the headless horseman for his “Legend” he was not the first to come up with the concept. Folktales from around Europe have headless horsemen of their own.

The Dullahan

Perhaps the most well-known of these tales in Irving’s time was that of the Irish “Dullahan.” Meaning “dark man” in Gaelic. The Dullahan was a harbinger of death in Celtic mythology akin to the Grim Reaper.  omewhat incongruously he was said to be the embodiment of a Celtic fertility god, Crom Dubh, who demanded decapitated blood sacrifices.

According to some stories, the Dullahan spent its nights driving a coach of headless horses and knocking on peoples doors. If you were unlucky enough to answer a “basin of blood” would be thrown in your face!  According to other stories, the Dullahan was a lone rider who carried his head under his arm and had a horsewhip made from a human spine. Wherever the Dullahan stopped his nightly ride, a person would drop dead.

The Brothers Grimm

Elsewhere in Europe stories of headless horsemen could be a little less gruesome. In German folklore, for example, the Brothers Grimm have recorded two stories which Irving, who travelled widely through Germany, may have heard.

In the first, the headless horseman is something of a guardian who appears to warn hunters not to go out on certain inauspicious days. In another, the headless horseman features almost as a bounty hunter tracking down criminals with the help of a pack of fire-breathing black wolves.

The Green Knight

In England the story of a headless horseman is almost comical.

In Sir Gawian and the Green Knight, a Middle English poem, the Green Knight rides into Sir Arthur’s court and rather arrogantly challenges any knight of the roundtable to decapitate him with his own axe. Rather obligingly, Sir Gawain takes up the challenge, and promptly cuts the Green Knight’s head clear off. Remarkably, according to the story, the Green Knight is able to pick up his own head off the floor and ride out of the court holding it under his arm.

American Folklore: the Legend of Sleepy Hollow

Whichever of these he found inspirational, they are not the only element of the legend that were inspired by stories he heard and events he experienced.

The central character of The Legend of Sleepy Hollow, the school teacher Ichabod Crane, was in fact a real man who Irving met in 1814. The real Crane was not a school teacher, but a colonel in the US Army during the War of 1812. Why Irving chose to name his school teacher after this man is unclear but we do know that he had another man in mind when filling out his character.

According to a notation by Irving, Ichabod Crane in the legend is actually based on a school teacher named Jesse Merwin. Iriving and Merwin became friends in 1809, when they lived in the same boarding house in a town called Kinderhook. While they lived there together, Irving and Merwin would frequently go hunting, and for 30 years afterwards they exchanged a lengthy correspondence. Merwin even named one of his sons after Irving.  

How much of the rest of the Legend of Sleepy Hollow is inspired by real life events or other stories is unclear. We don’t even really know if the story of the Hessian soldier who had his head blown off was true, but that’s exactly what makes the Legend so gripping. Irving was able to skilfully weave fact and fiction together so seamlessly that we aren’t sure were one ends and the other begins — a great testament to the American imagination.

It’s entirely plausible that a Hessian soldier did indeed get his head blown off at the battle of White Plains. Hessians were essentially mercenary German soldiers hired by the British to fight with them against the American revolutionaries, and two regiments of them did fight at the Battle of White Plains.

And the school house that Ichabod Crane worked at in the legend was a real place. You can even go visit it, although it has since been moved from its original location. 

Sleepy Hollow spinoffs

So, it’s natural to ask how much else in the story is based on historical events. Does a headless horseman in fact ride through the forests of Sleepy Hollow to this very day? The answer is probably not. But who knows?

What is unquestionably true, is that the story that Irving created is a gripping one that has since worked its way into American mythology, having been widely enjoyed by readers and widely adapted by later authors and film makers. Each one of these new storytellers has added his or her own own twist to the tale.

One of the earliest and perhaps the most famous spin-off is the cartoon adaptation of the story done by Walt Disney in 1949. Also called The Legend of Sleepy Hollow this cartoon is both spooky and a little comical. In Disney’s version, the head of the headless horseman becomes a pumpkin, which at the end of the film he throws at Ichabod as the school teacher flees.

More recent takes on the headless horseman legend include Tim Burton’s 1999 film, The Legend of Sleepy Hollow, featuring Johny Depp, Christopher Walken, and Christina Ricci. In it, Ichabod Crane is transformed from an awkward school teacher into a quirky New York police constable sent to Sleepy Hollow to investigate a series of gruesome decapitations.  

Then more recently, from 2014 to 2017, the television drama, Sleepy Hollow (which you can watch on Disney+) took the legend as its inspiration. In this version of the story, Ichabod Crane is a double agent spy who works for George Washington.

At the beginning of the series, Crane beheads a horseman who mysteriously refuses to die. The series has many plot twists and turns and Crane learns that if the headless horsemen ever retrieves his head, then the end of days will come.

Just as Irving adapted the stories of the headless horseman that he surely heard in Europe, each further adaptation of the legend builds on previous depictions in ways that are relevant to their contemporary audiences.    

Visiting Sleepy Hollow

If after reading the Legend of Sleepy Hollow and watching the fanciful Tim Burton version of the story (featuring you and handsome versions of Johnny Depp and Christopher Walken) — or the TV show if that’s your thing — and you fancy taking a look around the place yourself, visiting Tarrytown and Sleepy Hollow is easy.

Sleepy Hollow is just north of Tarrytown, and was up until 1996, known officially as North Tarrytown. But to capitalize on the village’s tourist potential, the residents decided to officially change the name to Sleepy Hollow.

The nearest airports to Sleepy Hollow are either New York’s John F. Kennedy International Airport or Newark International located in New Jersey. Since both are just to the south of New York City, combining your trip to Sleepy Hollow with a visit to the Big Apple is a great idea! Sleepy Hollow is located just 48 km (30 miles) away. 

Your best bet for getting there is probably to rent a car, since both Sleepy Hollow and Tarrytown are big, the hotels are not located within easy walking distance of the sightseeing spots.

Once there you do have a variety of hotels to choose from.  If you are able to splurge a little, the Castle on the Hudson is an appropriately spooky looking stone structure that you could imagine is host to a variety of paranormal inhabitants. It is also a spa so after a long day of headless horseman hunting, you can get a massage! For something a little more reasonably priced check out the Crabtree’s Kittlehouse

There are all sorts of places to check out in Sleepy Hollow!

First you might stop off at Washington Irving’s gravestone located in Sleepy Hollow Cemetery and say a few words. Also buried there are famous individuals such as the American industrialist of the late 19th Century, Andrew Carnegie, as well as William Rockefeller.

From there, head over to the “Headless Horseman Bridge” which, although it isn’t the “real thing,” is as the villages’ website says, “rustic enough for a selfie.” After that you could move on to visit the Christ Episcopal Church where Irving himself worshipped and which still has his marked pew at the front of the sanctuary.

You can then make your way to the amazing house, called Sunnyside, where Irving lived. It has been immaculately restored to look like the era in which he lived, and there are tours of the house led by guides in period-dress.

Both Sleepy Hollow and Tarrytown have plenty of restaurants, so there are a lot of options when it comes to dinnertime. The Hudson Farmer and Fish has great views of the Hudson River, and some delicious seafood (we hear).

But of course no trip to Sleepy Hollow would be complete without a proper ghost tour. Check out the Sleepy Hollow Cemetery’s website for more info on how to join one. Although times and dates vary, its best to schedule your trip on a weekend as it seems Saturdays are when the tour runs most often.  

As always, let’s check out what the grumpy guys on TripAdvisor say about their trips to Sleepy Hollow:

Of the over 500 people who reviewed the Sleepy Hollow Cemetery, it received fewer than 40 average or below-average ratings, so take these with a grain of salt. John V. who reviewed in 2020, said the manager of the place was real “nasty guy” though he doesn’t elaborate on why. Gabby C. found the tour guide of the night “gas lantern” ghost tour to be “incredibly rude” but again, gave no further insight.

Looking for spooky walks down history lane? Check these out:

  • The San Fernando Cathedral in San Antonio, Texas, has a history worth hearing.
  • Learn about the most infamous pirate queens to lurk on the seven seas.
  • Hang out with our good friend Lockey and a few other water-dwelling monsters.
  • Visit the Oregon coast for a spooky lighthouse tale.

The Lady Dicks did not just magically come up with this information themselves, they, in fact, did research beyond Wikipedia (thanks jerky iTunes reviewer for your one-star comment), and here are those sources:


The Lady Dicks was created by Tae Haahr. The Lady Dicks are Andrea Campion and Tae Haahr. “The Ghost Town of Old Cahawba, Alabama” was written by Justin Krause, produced by Tae Haahr, and edited by Rory Joy. The Lady Dicks theme music, A Pink Panther, is licenced through AudioJungle.

Written by

Justin Krause

Justin Kraus is a historian and educator. Since he could legally leave the house, he has been off writing and traveling around world. He is a bit older now but still learning. If you want to learn with him or have him write something up for you, he can be reached at kraus.justin@gmail.com.