The Legend of Sleepy Hollow


By John J Kerecz

Washington Irving (1783-1859) was an author, essayist, biographer, historian, and diplomat. Born in a prominent New York City merchant family, he became interested in writing at an early age, and in 1809 wrote his first major book, A History of New-York from the Beginning of the World to the End of the Dutch Dynasty, a satire on the city and contemporary politics.

A decade later while residing in England, Irving sent to his brother in New York a series of essays and short stories.  The collection included Irving’s two most well-known stories, “Rip Van Winkle” and “The Legend of Sleepy Hollow,” which featured the headless horseman.

In the Legend of Sleepy Hollow, Ichabod Crane a Connecticut schoolteacher, arrives in Sleepy Hollow in 1790 and is immediately attracted to the supernatural tales told in the area, particularly the tale of a headless horseman. According to the story, he is a cavalryman who was decapitated during a battle in the American Revolution. Each night he rides out searching for his lost head.

Crane also spends his time pursuing a young woman, Katrina Van Tassel, the “plump,” 18 year-old daughter and sole child of a wealthy farmer. This infuriates a rival for Katrina’s hand, “Brom Bones” Van Brunt, a handsome but rather rowdy and brutish man who subjects Crane to ridicule.

One Autumn night after attending a party at the Van Tassel home, Crane encounters the headless horseman near a bridge and the Sleepy Hollow Cemetery.  A pursuit through the countryside follows during which the spectral horseman hurls his “head” at Crane. The next day the schoolteacher is missing, leaving behind a rider less horse, a trampled saddle, Crane’s hat, and a smashed pumpkin.  Irving leaves it to the reader to decide if the horseman was an actual specter or Van Brunt in disguise.

When a yellow fever epidemic hit Manhattan in 1798, Irving’s family sent him to live in Tarrytown, north of New York City.  It was while there that he became familiar with the nearby area of Sleepy Hollow and its local ghost stories.  Irving loved the area so much that it became his permanent home in 1835.


This ghost story still retains its popularity nearly 200 years after its creation. The story has been the basis of stage plays, television presentations, movies, and even an opera.  The three most noted movies are: a 1922 silent feature, The Headless Horseman, starring humorist Will Rogers; as part of the Walt Disney 1949 animated feature, Ichabod and Mr. Toad; and, Tim Burton’s 1999 Sleepy Hollow, starring Johnny Depp.  In the last version, Crane (Depp) is a New York policeman sent to investigate a series of decapitation murders.


The real Sleepy Hollow is a village in Westchester County, New York.  It is located on the eastern bank of the Hudson River about 30 miles north of midtown Manhattan in New York City. Originally known as North Tarrytown, it was given its current name in 1996 of Sleepy Hollow when residents voted to have it changed to honor the Washington Irving story.  To the south of Sleepy Hollow is the village of Tarrytown.

This real village is the location of Sleepy Hollow Cemetery, where Washington Irving, the author of “The Legend of Sleepy Hollow,” is buried, along with Andrew Carnegie, Walter P. Chrysler, Brooke Astor, Elizabeth Arden, Thomas J. Watson of IBM, Samuel Gompers, and many others famous people. Philipsburg Manor House and the Old Dutch Church of Sleepy Hollow are located in the village as well.