The Legend of Sleepy Hollow

By Lukas Dammer and Tate Robertson 10/26/23

Have you ever heard of the Headless Horseman? For over two hundred years the terror of Sleepy Hollow has been remembered by many names such as the Galloping Hessian, Gan Ceann ,Dullihan,  but the most prominent of all, the Headless Horseman!  The WGP foundation states that the legend of the famous horseman prompted the village of North Tarrytown to change its name to Sleepy Hollow. Although the story is very well known, sometimes facts get very mixed up. For example, one student at EJHS thought that the Headless Horseman had a horse head.

A portrait of Washing Irving, author of The Legend of Sleepy Hollow.

The Legend of Sleepy Hollow was created by Washington Irving. Irving was born in New York and was the youngest of his seven siblings. Both of his parents immigrated there some years ago.


The original story of Sleepy Hollow focuses on the main character, Ichabod Crane, who is a schoolmaster at Sleepy Hollow, a town full of supernatural occurrences and stories of these occurrences. A town favorite is the tale of the Headless Horseman, a ghost of a Hessian mercenary who lost his head.

The story starts when a man named Ichabod wants to marry Katrina van Tassel, the daughter of a wealthy landowner. He planned to ask her at a gathering, but she had another suitor, Brom Bones. After being rejected, Ichabod leaves the social gathering in an agitated state. Hearing many ghost stories at the gathering, he sees ghosts and goblins everywhere he looks until finally, he sees an enormous hulk, the Headless Horseman. The Headless Horseman matches the pace of Ichabod and then he finally takes chase of Ichabod. He sees a nearby bridge and tries to get there before getting caught by the Headless Horseman. Ichabod reaches the bridge but gets hit by a pumpkin who falls off his horse and passes out. The next morning the people of the town find Ichabod's belongings on the bridge and a smashed pumpkin.

The Horseman has many unsettling habits. Eric Peden, a student at EJHS, said, “Every night he rises from his burial place, jumps on his horse and rides through the valley looking for his lost head.” The WPG foundation says that after he died, he tethered his horse to graves in the churchyard, and then set out to look for his missing head. He also is depicted with many different weapons, such as an ax, or a flaming jack o'lantern. The headless horseman symbolizes the past that never dies, but always haunts the living. There are many local landmarks in the area of Sleepy Hollow, such as the Old Dutch Church, Raven Rock, and the secluded valley.

A painting depicting the chase of the headless horseman.

The Headless Horseman has been a story told for many years and will most likely be told for many more generations to come.