The Headless Hessian – Perhaps the Real-Life Inspiration Behind the Legend of Sleepy Hollow

Following defeats in Brooklyn and Manhattan, the American army was forced to flee into Westchester County, New York (AKA Sleepy Hollow) after having been routed by William Howe’s combined British and Hessian forces in New York City.  General Howe has sailed a formidable force up the Hudson River and landed several thousand troops behind Washington’s retreating army.  Howe plans to cut off the American retreat route and end the rebellion in one decisive battle (the always unfulfilled dream of all generals).  This battle ultimately happened just north of White Plains, New York.

Hessian artillerymen and American cannoneers traded thousands of rounds of solid ball and grapeshot before the Hessians and Americans clashed in a brutal battle.  The Americans steadfastly held their ground but were ultimately forced to surrender the battlefield to the massively superior Crown Forces.  There were over 500 casualties that day, mostly Hessian and American, killed by cannon fire.

A legend will be born out of the Battle of White Plains—”the Headless Horseman”.  During the battle charging Hessian soldiers, attempting to advance largely uphill, were mowed down by American cannonballs which literally ripped through their advancing lines and took limbs, bodies and heads with them as they flew through the air or skipped across the ground.  One luckless Hessian is said to have had his head blown clean off but witnesses reported that corpse still moved and twitched on the ground for hours after he had fallen.  As night fell and the battle subsided his comrades came and retrieved his headless body and carried him for several miles to the small village of Sleepy Hollow where his body was interred in a nameless grave outside the Old Dutch Church.

To this day the ghost of this headless Hessian soldier may still haunt the tranquil roads and byways of Westchester County in and around Sleepy Hollow, searching for his severed head, and all the while carrying a ghastly jack-o-lantern as a macabre replacement.  This legend inspired Washington Irving’s short story The Legend of Sleepy Hollow first published in 1820 as part of a larger work entitled The Sketchbook of Geoffrey Crayon, Gent.

While the The Legend of Sleepy Hollow is clearly fiction, it contains references to many real historical places and people.  The Old Dutch Church where the body of the headless Hessian soldier was brought by his comrades according to folklore, features prominently in the tale and Irving’s, Ichabod Crane, may have been a man named Ichabod Crane from Westchester County who enlisted in the Marine Corps in 1809 at about the age of twenty and served the Corps for forty-five years.  This real-life Ichabod Crane may have disappeared from the local community, not because he was fleeing from the headless horseman, but because he too was heartbroken by unrequited love and was seeking to run away and make a new life for himself.