The Legendary Legend of Sleepy Hollow

The author, Mr. Washington Irving, was one of the most famous American authors of the 19th century and was often referred to as the “first American man of letters.”

He was born in New York City on April 3, 1783, to parents who immigrated from England twenty years prior. While his older brothers were required to attend college, Washington was not. He worked in the law office of Josiah Ogden Hoffman and fell in love with his daughter, Matilda. While working in this office and starting his life with Matilda, Washington began writing satirical essays in his brother’s newspaper, The Morning Chronicle. 

Washington took the bar examination in late 1806 and became a lawyer. However, he continued to write and released multiple historical essays. He took a break from writing after Matilda suddenly died in April 1809 and continued to work as a lawyer. He traveled to Liverpool in 1815, where he met the Scottish novelist and historian Sir Walter Scott, who inspired Washington to write again. 

Washington then released The Sketch Book of Geoffrey Crayon in 1820. This was a collection of 34 essays and short stories that mixed fact with fiction. Washington released the stories under the pseudonym Geoffrey Crayon to try to distance himself from his previous work. Since he was already an established writer, historian, and lawyer, he wanted people to read and review his work authentically.

Among the short stories were two of his most famous works: Rip Van Winkle and The Legend of Sleepy Hollow. Both of which were inspired by Washington’s time spent in the Hudson Valley region of New York. 

The Legend 

The legend is set in 1790 near a very real place called Tarrytown, New York. Sleepy Hollow was originally incorporated as North Tarrytown, but the village adopted its current name in 1996. 

Sleepy Hollow is a small town with about 10,000 people. Most people still consider it part of Tarrytown and the surrounding communities.

The Legend of Sleepy Hollow begins with an explanation that it was “found among the papers of the late Diedrich Knickerbocker.” Washington Irving or Diedrich Knickerbocker does an amazing job at describing this sleepy little town where “a drowsy, dreamy influence seems to hang over the land.” 

The area is peaceful, but almost too peaceful in a way that is a bit chilling. There is a supernatural, spiritual feeling that looms over everyone, but is just accepted as part of that town. 

The main character of the legend is an awkward schoolteacher named Ichabod Crane. This is just part of his description in the story: “He was tall, but exceedingly lank, with narrow shoulders, long arms and legs, hands that dangled a mile out of his sleeves, feet that might have served for shovels, and his whole frame most loosely hung together. His head was small, and flat at top, with huge ears, large green glassy eyes, and a long snipe nose, so that it looked like a weather-cock perched upon his spindle neck to tell which way the wind blew. To see him striding along the profile of a hill on a windy day, with his clothes bagging and fluttering about him, one might have mistaken him for the genius of famine descending upon the earth, or some scarecrow eloped from a cornfield.” 

Even though he is described as lanky and thin, the women of the town love him. At this time, teachers lived with their students and their families. The ladies loved having Ichabod at their homes, and it was noted that “he was a kind of travelling gazette, carrying the whole budget of local gossip from house to house.” 

But, there was one woman Ichabod liked more than anyone, and that was Ms. Katrina Van Tassel, the daughter and only child of a rich Dutch farmer. Pretty sure Ichabod loves her riches and the amount of food she can afford more than he loves her, but either way, he wants to court Ms. Katrina. 

This is an issue because a man named Abraham Van Brunt, also known as Brom Bones, also wants Ms. Katrina. Brom Bones tries to fight Ichabod for Katrina, but when the scarecrow refuses to fight, the big bad Brom starts harassing Ichabod with pranks and cruel jokes. But Ichabod does not back down. 

Ichabod, Brom, and most of the town are invited to a harvest party at the Van Tassel home. At this party, Ichabod listens to party guests share scary stories, including the tale of the Headless Horseman, also known as the Galloping Hessian of the Hollow. The horseman is said to tether his horse nightly among the graves at the Old Dutch Church and haunt the countryside. The church and a nearby wooden bridge were the Horseman’s favorite spots to haunt. 

After listening to the stories and describing food in great detail, Ichabod shoots his shot with Katrina and is shot down, so he leaves the party on a horse named Gunpowder. As he rides Gunpowder through the woods, he becomes more and more terrified, like anyone would after listening to scary stories and then leaving a party alone. 

Washington wrote: “All the stories of ghosts and goblins that he had heard in the afternoon now came crowding upon his recollection. The night grew darker and darker; the stars seemed to sink deeper in the sky, and driving clouds occasionally hid them from his sight. He had never felt so lonely and dismal.” 

Then he began to approach the very spots that were mentioned in the stories. It began with an enormous tulip tree, then a swamp known as Wiley’s Swamp, which featured the bridge haunted by the horseman. This is where Gunpowder becomes the real villain of the story. He stops listening to Ichabod and starts running all over the place, refusing to cross the bridge, which would bring him to safety. Instead, he’s running alongside it and stopping just short of the bridge. 

Then, Ichabod sees the Headless Horseman, who seems to be following him. The legend goes, “The stranger, however, quickened his horse to an equal pace. Ichabod pulled up and fell into a walk, thinking to lag behind, - the other did the same…On mounting a rising ground, which brought the figure of his fellow-traveller in relief against the sky, gigantic in height, and muffled in a cloak, Ichabod was horror-struck on perceiving that he was headless! - but his horror was still more increased on observing that the head, which should have rested on his shoulders, was carried before him on the pommel of his saddle!” 

Gunpowder starts running frantically in every direction except toward the bridge. According to the legend, the horse seemed possessed, and Ichabod couldn’t do anything to control him. The chase is so extravagant that Ichabod loses his saddle and has to ride bareback, holding onto Gunpowder’s neck. Finally, Gunpowder gets Ichabod over the bridge, which should make him safe from the horseman, but…the horseman catches up and throws his pumpkin head at Ichabod, who is knocked off Gunpowder. 

The next day, the horse is found, without his saddle or rider. Ichabod was never found, but his hat and the pumpkin were. Soon enough, the disappearance of Ichabod Crane became a town legend. Many believed it was the vengeful spirit of the horseman. Others believed it was Brom posing as the horseman.

Real Life Inspiration 

While The Legend of Sleepy Hollow is considered to be one of America’s first ghost stories, it’s certainly not the first tale of a headless horseman. Many stories feature a headless horseman, including those written by the Brothers Grimm and Washington’s mentor, Sir Walter Scott. 

Sir Walter Scott published The Chase in 1796, which is a translation of a German poem by Gottfried Burger called The Wild Huntsman. Both of which feature headless men on horseback. There is also a creature in Irish folklore called the Dullahan, which is depicted as a headless rider on a black horse who carries his own head. There are other headless horsepeople in German, Welsh, Scottish, and English folklore. 

According to the New York Historical Society, there was a real Hessian soldier who was decapitated by a cannonball during the Battle of White Plains around Halloween in 1776.

Ichabod Crane is said to be inspired by a real schoolteacher named Jesse Merwin. This is someone Washington Irving actually knew. Jesse Merwin was a long-time resident of Kinderhook, New York, one of the Hudson Valley communities that inspired Sleepy Hollow. 

Just like Ichabod, Jesse would board with the families of his students. In 1809, Merwin was boarding with Judge William P. Van Ness at the same time Washington was visiting. The two had an immediate connection, and they stayed connected after Washington left Kinderhook to continue his travels. One of these letters is signed with, “From Jesse Merwin, the original Ichabod Crane.” 

Washington Irving moved to Tarrytown in 1798 to flee a yellow fever outbreak in New York City. The area itself inspired the creation of Sleepy Hollow, but specific places in the area made their way into the story. 

The Van Tassels and their home were inspired by the real-life Mott family. Historian Edgar Mayhew Bacon wrote in his 1898 book Chronicles of Tarrytown and Sleepy Hollow that Washington Irving was a frequent visitor to this house, and his sister even lived there for some time. This was expanded on in 1975 by historians Jeff Cannin and Wall Buxton, who added that the area was once owned by John Van Tassel.

Wiley’s Swamp was once a real place, but it’s no longer there. However, there is a brook that runs through a public park that people can visit. This park is also the site where British spy John André was captured and exposed Benedict Arnold’s plan to rat on America to the Brits. 

In real life, the spot is honored with a monument. In the legend, the Headless Horseman begins chasing Ichabod at this very spot, and the spot is rumored to be haunted by the very ghost of John André. 

The bridge where Ichabod disappeared was also real, but it is no longer there. There were actually five bridges that could’ve been inspired by the story. However, according to the legend and the historians who traced Ichabod’s chase with the horseman, Ichabod disappeared inside what is now the Sleepy Hollow Cemetery. 

In the legend, the bridge leads to the yard of the Old Dutch Church. This features the cemetery with the people in the story, including Katrina Van Tassel and the Headless Horseman. 

While sharing stories at the Van Tassel’s, someone mentioned one of “the woman in white, that haunted the dark glen at Raven Rock, and was often heard to shriek on winter nights before a storm, having perished there in the snow.” Well, Raven Rock is a real rock configuration located in the Rockefeller State Park Preserve. Whether or not it’s haunted by a woman in white has yet to be confirmed or denied. 

There are landmarkers and plaques at these locations explaining their significance to the story. There are also just huge monuments and statues of these characters. There is a place called Phillipsburg Manor, which is rumored to have inspired the place where Ichabod would stroll and gossip with the girlies. 

At this location is a granite sculpture that depicts Ichabod Crane fleeing from the Headless Horseman with the Old Dutch Church in the background. There is a statue of the Headless Horseman chasing Ichabod Crane on the Route 9 median between Philipsburg Manor and the Old Dutch Church. This is an 18-foot-tall sculpture, and it’s one of the most visited spots in Sleepy Hollow for obvious reasons. 

Adaptations 

This story is so old that the first few adaptations were silent films. The longest version was the 1922 silent film directed by Edward D. Venturini. 

The most popular adaptation is the 1999 version directed by Tim Burton starring Johnny Depp as Ichabod Crane, Christina Ricci as Katrina Van Tassel, and Christopher Walken as the Headless Horseman. 

There’s a television series called Sleepy Hollow, which was released in 2013 and has 4 seasons. This follows Ichabod Crane after he rises from the dead centuries after he disappeared. Ichabod Crane in modern day, solving mysteries.