Legend of Sleepy Hallow. Fact or Fiction?


Day 7 of the 31 Days of Myths, Magic, Mayhem, and more…

I will be your host for the evening, and tonight, we will dive deep into the mystery of the Legend of Sleepy Hallow.

Before we dive into the myth, I want to mention that one of my bucket list places to go is Sleepy Hallow Cemetery. It is the final resting place of some fantastic people:

Francis P. Church- who penned ‘Yes, Virginia, there is a Santa Claus.’

Andrew Carnegie- one of the wealthiest Americans in history and founder of Carnegie Steel.

Angelica Hamilton- the eldest daughter of Alexander Hamilton who suffered a mental break after her brother Philip died of injuries resulting from a duel with George I. Eacker. According to reports, she experienced a disintegration of the mind so profound that it was described as ‘eternal childhood.’ She is mentioned twice in the world-famous musical- Hamilton.

And of course-

Washington Irving- author of Sleepy Hallow and many other books, historian, 1st Chairman to what would become the New York Public Library, and American Ambassador to Spain.

Sleepy Hallow, New York.

Most people don’t know that Sleepy Hallow does exist. However, I would not be a good historian if I failed to mention that its name was not officially ‘Sleepy Hallow’ until 1996. But it is still the same area that Washington Irving explored in the 1790s, and the story Legend of Sleepy Hallow is based on the location.

Recap of the story

Trying to recap an Irving story is unnerving, but I will give it a go.

The story opens with a note that the following incident was found written among the papers of a deceased man named Diedrich Knickerbocker.

Ichabod Crane has just arrived in town as a schoolmaster. He is exceptionally tall, thin, and lanky, with a flat head and a long beak-like nose, giving him the appearance of a scarecrow. He is fascinated by books, food, and wealth and has ambitions to court the wealthy heiress Katrina van Tassel despite her being sought after by a local- Brom Bones.

Crane feels like he has won over Katrina and plans to ask for her hand in marriage at a party that her family is throwing. When he arrives, he ignores poor Katrina and spends all his time at the food table, then later on the dance floor, trying to impress her with his moves. The group huddles together and shares ghost stories when the party eventually starts winding down.

This is when the tale of the headless horseman emerges. A figure shrouded in mystery can be seen galloping across Sleepy Hallow at night, yet unable to cross the church bridge. Brom Bones boasts of having raced and won against this strange creature, probably to impress the young Katrina. Crane goes on to share his own ghost stories, but it doesn’t compare to coming face-to-face with a real ghost.

At the end of the party, Crane pulls Katrina aside, and it appears that he proposed marriage but got turned down. Unfortunately, we can only guess what was said between them since the text does not mention it. A defeated Ichabod heads home and finds himself chased by a headless horseman. The horseman throws a pumpkin at Ichabod, which causes him to tumble off his horse and vanish without a trace.

The townspeople set out to find Ichabod and eventually arrived at the church bridge. They stumbled upon his hat and a broken pumpkin, but no sign of the Ichabod. His disappearance became a local legend: some thought he had been taken by the Headless Horseman; others maintained that Brom had tricked him. Years later, an outsider visiting the area swore that Ichabod was alive and well in Manhattan, having made a fortune as a lawyer, politician, writer, and judge. Meanwhile, Brom, who had married Katrina, always laughed when someone mentioned the smashed pumpkin.

The story is concluded with an afterthought from Diedrich Knickerbocker, who says he has written down the tale as it was told to him. He portrays the story’s narrator as an older rural man with a hearty humor. Most of those listening responded with laughter, except for another elderly man, tall and with a stern face. The mysterious man asked the storyteller to explain the moral of his story. The answer included three lessons: take a joke in stride, don’t compete against someone you’re sure to lose against, and some losses open up better possibilities down the road. The postscript implies the storyteller might be Brom or Ichabod but is left open to speculation.

The legend behind the story.

Now, when it comes to understanding inspiration for writers- the truth is in the eyes of the reader. Historian Elizabeth Bradley (Historic Hudson Society) believes that the story may be based on Sir Walter Scott’s poem, The Chase, which is based on a translation of a German poem, The Wild Huntsman, by Gottfried Bürger. According to Bradley, “The poem is about a wicked hunter who is doomed to be hunted forever by the devil and the ‘dogs of hell’ as punishment for his crimes.”

Now, I see some similarities, so Sir Walter Scott may have been inspired by it.

The folk tale narrates the tale of Earl Walter and his unyielding ambition to hunt. He is depicted as an unfeeling and careless character who, despite warnings, sets out on a hunt during “God’s own hallowed day.” In addition, two otherworldly entities join him – one heavenly and another devilish.

The two entities attempt to convince Walter to either quit the pursuit or to keep going no matter what anyone else says. The song mainly focuses on how the affluent mistreat the underprivileged. This is seen in three parts of the ballad: the angelic figure repeatedly asking Walter to abort his mission, Walter disregarding the warning, and ultimately being divinely punished.

But then again, the New York Historical Society believes that the story was based on a Hessian soldier who was decapitated during the Battle of White Plains in Oct 1776. In 1798, Major General William Heath released an autobiography that detailed his time during the Revolutionary War. In it, he mentioned a famous tale of a headless Hessian soldier. On November 1, 1776, Heath wrote in his journal, “A shot from the American cannon at this place [White Plains] took off the head of a Hessian artillery man.” White Plains is located less than ten miles from Sleepy Hallow.


I have no idea where Washington Irving got his inspiration, and it doesn’t matter. It’s a great story to tell this time of year. It has been made into countless movies, and the headless horseman is an iconic figure for Halloween, so it deserves its own spotlight in my 31 Days of Halloween.

“Ichabod was horror-struck on perceiving that [the horseman] 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…”

The Legend of Sleepy Hallow

If tales of legend, myth and fantasy topped with a nice cup of coffee interest you, I suggest taking a look at my book The Writer and the Librarian. It’s a historical fantasy about a middle-aged woman faced with a decision: accept what is written in books or find out for herself the truth behind the stories. Now available on

Amazon: https://a.co/d/flQhakX

Barnes and Noble: The Writer and the Librarian by Rose Geer-Robbins, Paperback | Barnes & Noble® (barnesandnoble.com)

Target: The Writer And The Librarian – (the Raven Society) By R L Geer-robbins (paperback) : Target

And on any of your favorite Indie Book Store website!

What are your thoughts?

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