The Man Who Forever Sleeps in Sleepy Hollow: The Real Legend of Sleepy Hollow

As an annual tradition since 2020, I have liked to go on fall trips where I look for places that are haunted or have spooky significance. I decided to do a road trip with my mom and sister to the oldest part of early America and part of the original 13 colonies. Being the oldest part of the nation, it is bound to have many ghost stories, whether actual sightings or works of fiction. My first stop will be in Sleepy Hollow, New York, a tale of a suspenseful chase of a headless horseman pursuing a schoolmaster on horseback. Today, I will start with an iconic Halloween fiction work, The Legend of Sleepy Hollow. 

When I was a kid, I had a lot of Disney VHS tapes in my collection. When I did not use the tapes and covers as building blocks, I watched the Disney Classics Collections hours on hours. Among many of my tapes, one was Walt Disney’s Ichabod and Mr. Toad. This would be my first introduction to The Legend of Sleepy Hollow. This adaptation had Bing Crosby narrate, sing, and voice Ichabod Crane. Years later, I learned that Disney's short was one of the more accurate adaptations of the original story. 

Other factors helped keep Sleepy Hollow relevant to me. Growing up, Cartoon Network would make television movie adaptations of the Legend of Sleepy Hollow, which further retained my familiarity with the story. 

I would go into more depth of the story when, in 8th grade, we had to read it to understand how the rising plot and climax of stories work, as well as a more in-depth look at the author, Washington Irving. 

Sleepy Hollow Summary

For those unfamiliar with the story or need a recap, this eerie tale tells of a schoolmaster, Ichabod Crane, who recently came into the little village of Sleepy Hollow. He is known for being superstitious. He develops a rival with the character Brom Bones, who would nowadays be compared to sort of a high school jock archetype, both competing for the affections of the beautiful Katrina Van Tessel, who is from a wealthy family. Katrina rejects Ichabod and leaves the party alone on horseback on a cold autumn night. 

While riding on horseback one night back home, he hears an evil laugh behind him. It is of the ghostly specter of a decapitated Hessian soldier holding a flaming jack o'lantern known as the Headless Horseman. He pursues Ichabod through the woods. Fear and tension build up between Ichabod and the reader as he frantically evades the Headless Horseman. 

He eventually gets to a bridge where he makes a last-ditch effort to cross it. Crossing it would mean he was home free as the Headless Horseman would not cross the bridge. As Ichabod and his horse darted across the bridge, he looked back to see a Jack-o-Lantern head getting closer and closer to him. The phantom threw his pumpkin head at Ichabod, where his fate would be sealed. Ichabod never made it across the bridge. It was as if he vanished into thin air.  No one ever saw Ichabod Crane again.  

The Real Sleepy Hollow

The closest you will get to this story being real is the fictional town of Sleepy Hollow, which is the setting for the ghost story. This town held a special place in the heart of Washington Irving. Sleepy Hollow is near Terrytown, which is located by the Hudson River.  The population of Sleepy Hollow is 11,001, according to a 2022 census. 

Washington Irving bio and love for ghost stories

First, I want to give a brief bio of the author himself. Washington Irving was born in 1783 and was named after the first United States president, George Washington. Irving actually met Washington during his childhood while in town with his Nanny. According to Irving, George placed his hand on his head and blessed him for having the name Washington. He would remember that moment and the pressure of Washington’s hand on his head for the rest of his life.

Growing up, Irving was fascinated by ghost stories told by the locals he grew up around. This fascination would play a huge role later in his life when he wrote one of his best-known works.

Connection to Sleepy Hollow

In 1798, Irving moved to Terrytown to avoid the yellow fever outbreak in New York City.

Living in a Sleepy Hollow, he was fascinated by stories from the Dutch. In 1835, Irving purchased a 10-acre estate called Wolfert Roost, which he renamed the estate to Sunnyside. Initially, the land was owned by Wolfert Acker and then passed down through his family until it was sectioned and sold off.  Irving would still honor the former name by referencing it in his work, such as Wolfert’s Roost and Miscellaneous.  Believe it or not, however, Washington Irving wrote the story during his stay in Birmingham, England. 

Into The Headless Horseman Verse

In The Legend of Sleepy Hollow, Irving narrates how the Headless Horseman is the ghost of a Hessian Soldier who roams the cemetery on horseback in the evening looking for his lost head and then vanishes during daybreak.

He also had a mentor named Sir Walter Scott who wrote a poem about a wicker hunter who the devil hunted. 

Earlier ghost stories of horse-riding apparitions appeared way before Sir Walter Scott’s, let alone Washington Irving’s. Tales such as these actually go way back to the Middle Ages in Europe. There are different versions of the tale, with either the headless horseman carrying his decapitated head or not carrying a head. Many of them stem from the UK and Germany.

England- A famous story from England comes from the King Arthur story Sir Gawain and the Green Knight involves a knight who appears before King Arthur’s Round Table and challenges one of his Knights, Gawin, to behead him. After he beheads him while decapitated, he tells Gawain he must let him behead him next to test his loyalty as a knight in a year. He goes through trials and ends up with only a cut at the nape of the neck after proving to the Green Knight his nobility. So, it's a little bit of a happier but strange ending. 

Ireland—There is a fairy called the Dullahan, who was a cherished Celtic god until the arrival of Christianity in the 6th century. The Callahan takes the form of a headless coachman and is said to appear at the doorstep before someone’s death. It is said that despite his head being decapitated, he has the ability to see those about to die.

Scotland—Their version of a headless horseman is the ghost of a man named Ewen, who was decapitated during a clan clash at the Island of Mull. In this version, not only is the rider headless, but the horse is as well. 

Welsh folklore - there are not only headless horsemen but women as well. Fenyw heb un pe or The Headless Woman in English, rides a headless horse. For those dying to know the horse’s Welsh name, it is Ceffyl heb unpen. 

German - This version of the Headless Horseman can kill his victims by just touching them. He takes the form of a spirit called a revenant, a walking corpse raised from the dead to haunt the living. Another tale paints the horseman in a more heroic light, who warns the living when danger is afoot and hunts down evil souls. 

We also have one more Headless Horseman tale in America. This one roams the state of Texas. The story began to surface in the mid-1800s, roughly a couple of decades after The Legend of Sleepy Hollow was published and Americans started moving west. If I ever go to Texas, I will also be sure of that story, living in America. This one is called El Muerto.  He is the spirit of a man captured and beheaded for stealing horses. This ghost is said to keep his head in his saddle bag. His horse’s hooves pound the ground so loud one can compare it to thunder.  

Sleepy Hollow Cemetery

“He sleeps his last sleep in the little cemetery of Sleepy Hollow.” 

       -Geo. H Boughton (talking about Irving’s final resting place.)

On November 28, 1859, Washington Irving passed away. Before his death, he published an autobiography on George Washington. He cherished Sleepy Hollow so much that he wanted to be buried there. His body was laid to rest in Sleepy Hollow Cemetery. 

Today, Sleepy Hollow Cemetery not only still functions as a cemetery but is also an arboretum with small signs identifying some trees. 

I scheduled a two-hour tour of the Cemetery to gain more insight into the Sleepy Hollow mythos. A small fenced-off burial plot had the words Irving on the gate. Washington’s tombstone was the only one with two American flags on each side. 

The Old Dutch Church and Burying Ground 

The church was built in 1697 and is the oldest church in the state of New York. The Old Dutch Church of Sleepy Hollow also has notable graves buried around it. It is across the street from Sleepy Hollow Cemetery. Often, the two places get mixed up as one cemetery when they are separate. Among them is a woman named Caterina Ecker Van Tessel. If the name sounds familiar, she inspired the character Katrina in the story. I was able to locate Caterina Van Tassel's grave, but I could not find Samuel Young or Wolfert's grave before closing. Caterina’s grave faded and was worn over the years, but it can still be found in Dutch and English. 

At one point, a man named Samuel Youngs, a friend of Washington Irving was also laid to rest there before having his remains relocated to a cemetery in Ossining Dale’s Cemetery in 1851. During his life, he was a school teacher and in his earlier years, he served as a lieutenant in the American Revolutionary War. Do you want to know who else was a schoolteacher? Ichabod Crane. That’s right! Ichabod Crane’s character was modeled after Irving’s friend.  Other sources state that some elements were loosely based on another schoolmaster who lived in upstate New York named Jesse Merwin. The namesake came from a colonel who served in the War of 1812, also named Ichabod Crane. 

Ichabod's Last Ride

Outside the cemetery, there is a bridge that cars pass over. On the sidewalk, there is a plaque telling of Ichabod's fateful moment in the story. After he is chased through the Old Dutch Church’s cemetery, he and his hose dart across a bridge, only for the Headless Horseman to throw his head at Ichabod. The bridge is the likely place Ichabod would have made his bid for freedom.

In movies 

This story has been the subject of movies and cartoons. The Walt Disney version, some television specials, and even Tim Burton had Sleepy Hollow creep into his mind, and he came up with a horror flick based on the tale. In Burton’s movie, Ichabod Crane (played by Johnny Depp) is a police constable who survives his encounter with the Headless Horseman and is sent to look into a crime plagues Sleepy Hollow. 

Closing

The Legend of Sleepy Hollow is a staple of Halloween folklore and a product of early American post-Revolutionary War. The story continues to be celebrated in modern-day Sleepy Hollow. Many tourists flock to the town to relive the moments in the Washington Irving ghost story. There are even costume riders on horseback to help visitors live through the tale and get some excellent photos for family and social media. 

This blog story will not be the only big haunt for this month, but OHH, there will be so much more. In the following story, we talk about the life of a well-known ghost/demon hunter duo and their famous cases, followed by a visit to one of their cases to an infamous house. I will also talk about Irving again around Christmas, as he plays a vital role in the American version of the guy in the red suit.