Therapedic | Blog - The Legend of Sleepy Hollow: Tale and Trivia (2024)

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Therapedic | Blog - The Legend of Sleepy Hollow: Tale and Trivia (1)

October 29, 2018

Considered by many to be a favorite scary story for Halloween parties or around a bonfire on a chilly fall night, The Legend of Sleepy Hollow by Washington Irving has a blend of fiction and historical fact that makes it one of the best-known short stories of American literature.

Irving brilliantly weaved details of real people and places into fictional ones that came to life in the story. And in a perfect case of life imitating art, in 1996 the village in North Tarrytown used as the setting in the 200 year-old story officially adopted the name Sleepy Hollow.

Therapedic | Blog - The Legend of Sleepy Hollow: Tale and Trivia (2)

As a refresher for those who haven’t heard or read it recently, the story takes place in the late 1700s in the very quiet town of Sleepy Hollow. School teacher Ichabod Crane settles there from Connecticut and finds himself at odds with a local, Abraham “Brom Bones” Van Brunt. over a woman named Katrina Van Tassel. One night after leaving a party at Katrina’s home, Ichabod encounters the Headless Horseman, the ghost of a soldier who was decapitated by a cannonball during the Revolutionary War and now haunts the area on his search for his head. After Ichabod is chased by the horseman and has his head thrown at him, he is never seen or heard from again.

Here are some fun facts about The Legend of Sleepy Hollow that perhaps could be spun into a trivia game along with telling the tale:

  • The fictional town of Sleepy Hollow was located in New York’s Hudson River Valley near the real Tarrytown.
  • The character Ichabod Crane was named after a career military man who served in the War of 1812, whom Irving met at Fort Pike in Sacket’s Harbor, NY in 1814.
  • However, the fictional Ichabod Crane’s mannerisms and behavior were inspired by a one of Irving’s friends from Kinderhook, NY, a teacher by the name of Jesse Merwin.
  • Brom Bones was a composite of two people that Irving knew – village blacksmith Abraham Martling and his son, also named Abraham, who was the village cobbler. Brom was derived from Abraham, and Bones was believed to be the nickname the blacksmith used for his skinny son.
  • The Headless Horseman is based on a Hessian soldier who was said to have been beheaded during the Battle of White Plains. The Hessians were German soldiers hired by the British Crown to fight the American colonists in the Revolutionary War.
  • There’s a German legend of the Headless Horseman that is said to have influenced the folklore of the Dutch, who inhabited the Hudson Valley and whose culture and traditions are found throughout Irving’s story.
  • Some of the names from the story, including Katrina Van Tassel, can be found on tombstones in the cemetery that grew around the Old Dutch Church in Sleep Hollow.
  • Washington Irving is buried in the Sleepy Hollow Cemetery, as well as other famous names such as Andrew Carnegie, Walter P. Chrysler and Elizabeth Arden.

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Therapedic | Blog - The Legend of Sleepy Hollow: Tale and Trivia (2024)

FAQs

What is the moral of The Legend of Sleepy Hollow? ›

The moral of The Legend of Sleepy Hollow is not to let superstition guide your actions and overwhelm your reason. Ichabod Crane is an intelligent man, but he has an unfortunate tendency to let his imagination run away with him. His superstitions influence his decisions, and this leads him to disaster.

Is there any truth to The Legend of Sleepy Hollow? ›

According to the New York Historical Society, others believe Irving was inspired by “an actual Hessian soldier who was decapitated by a cannonball during the Battle of White Plains, around Halloween 1776.” Irving's story takes place in the New York village of Sleepy Hollow, in Westchester County.

What does The Legend of Sleepy Hollow symbolize? ›

What does The Legend of Sleepy Hollow symbolize? "The Legend of Sleepy Hollow" symbolizes the conflict of man versus the supernatural. The supernatural exists everywhere around the town, or so the people believe. Ichabod's fear iis so great that he runs away after a supposed encounter with the Horseman.

Is The Legend of Sleepy Hollow hard to read? ›

Customers say

Customers find the book very enjoyable and simple to read. They also say the plot is great and ingrained in the cultural memory. Readers describe the book as great for kids and good for Halloween season. They appreciate the gorgeous illustrations.

What is the main point of The Legend of Sleepy Hollow? ›

The story primarily focuses on Ichabod's rich imagination and how it affects his behavior and guides his actions. He is frequently described as becoming lost in imaginative thoughts about the various foods he will eat, especially when he encounters the abundance of the Van Tassel farm.

What does the pumpkin symbolize in The Legend of Sleepy Hollow? ›

When he encounters the Headless Horseman, he bolts to cross the stream, assuming its natural properties offer some sort of magical protection from his supernatural pursuer. The smashed pumpkin left behind the morning after is a natural symbol for the supernatural horseman's missing head.

What happened to Ichabod Crane at the end of the story? ›

The chase ends when the horseman throws something at Ichabod and it strikes him in the head. Ichabod is never seen in Sleepy Hollow again, although his hat is found next to a smashed pumpkin.

Was Ichabod Crane real? ›

Col. Ichabod B. Crane definitely existed, and was a contemporary of Washington Irving's, but unlike the spindly bookish schoolteacher in “The Legend of Sleepy Hollow,” which Irving published in 1820, this Ichabod Crane did not run away. “He was a real person,” Dr.

Was Ichabod Crane the Headless Horseman? ›

Although the true nature of both the Headless Horseman and Ichabod's disappearance that night are left open to interpretation, the story implies that the Horseman was really Brom in disguise, using a Jack-o'-lantern as a false head, and suggests that Crane survived the fall from Gunpowder and immediately fled Sleepy ...

What is the main problem in The Legend of Sleepy Hollow? ›

The main conflict in 'The Legend of Sleepy Hollow' is between Ichabod Crane, the schoolteacher, and Brom Bones, a local man, who are in competition for the hand of Katrina Van Tassel. Katrina is a beautiful 18-year old who is the only daughter of a rich farmer.

What is the irony in The Legend of Sleepy Hollow? ›

In 'The Legend of Sleepy Hollow', situational irony is seen in Ichabod's failed expectations and the town's mistaken belief about the Headless Horseman. Dramatic irony occurs through the reader's awareness of Brom being the Horseman, Katrina's manipulation, and the town's unwitting storytelling truth.

Why is it called Sleepy Hollow? ›

“Sleepy Hollow” was the name of a small town or village in upper New York state. At the time of Washington Irvington's story, it was an isolated and peaceful town, hence the name “Quiet”. Hollows are like small valleys; low, level, hollowed out places between hills.

Is the Headless Horseman real in The Legend of Sleepy Hollow? ›

While skeptics of the supernatural could argue against the existence of this headless horseman, historical records show, according to the New-York Historical Society, that there actually was a real decapitated Hessian soldier.

Who is the antagonist in The Legend of Sleepy Hollow? ›

Abraham 'Brom Bones' Van Brunt is the main antagonist of the story. He vies for the affection of Katrina Van Tassel against Ichabod Crane.

How accurate is Sleepy Hollow? ›

As rooted in folklore as “Rip Van Winkle” and “The Legend of Sleepy Hollow” are, they are not, in fact, popular legends and myths that sprang up during the early years of the United States — they are works of fiction penned by Washington Irving. Largely forgotten today, Washington Irving has an odd historical legacy.

What is the overall theme of Sleepy Hollow? ›

The main themes in “The Legend of Sleepy Hollow” are myth and folklore, city and country, and morality. Myth and folklore: The telling of tales plays a prominent role in the haunted town of Sleepy Hollow, and the story itself is written in the form of a local legend.

What is the meaning of Sleepy Hollow? ›

“Sleepy Hollow” was the name of a small town or village in upper New York state. At the time of Washington Irvington's story, it was an isolated and peaceful town, hence the name “Quiet”. Hollows are like small valleys; low, level, hollowed out places between hills.

What is the author's purpose of The Legend of Sleepy Hollow? ›

Final answer: Washington Irving's 'The Legend of Sleepy Hollow' primarily aims to entertain readers with a tale rich in folklore and supernatural elements, while also preserving early American cultural traditions and exploring themes of imagination versus reality.

What is the allegory of The Legend of Sleepy Hollow? ›

When readers understand that the rivalry in Irving's “The Legend of Sleepy of Hollow” is not only between the opposing forces of two characters, but also between an underdog and a powerful bully, then they can understand a central allegory of the story: an allegory of a young and developing America.

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