The Headless Horseman, a Hessian soldier on horseback, is said by Washington Irving to "tether" his horse among the headstones of the Old Dutch Burying Ground of Sleepy Hollow; "One would think that there the dead, at least, might rest in peace." Sadly, there is no peaceful repose for the Headless Horseman, for he has business to perform each night.
The nocturnal occupation of this spirit is to discover where it was that he lost his head. Failing that, he will set about looking for the head of some other unfortunate person. In the Headless Horseman's search for his own head, he could be doomed to search for eternity, for his rides do not seem to extend past the colonial town of Sing Sing (present day Ossining) to the north, or "Andre Brook" (at Patriots' Park in Sleepy Hollow) to the south. If one considers the Battle of White Plains, however, there may be good reason to believe that his head lies elsewhere. The battle's anniversary is observed about Halloween time.
In October of 1776, Washington and his army were in serious trouble. They were making a strategic withdrawal through Westchester County inspired by dire necessity, and the line-of-march was directed toward White Plains from Manhattan. Why White Plains? Apparently because it stood sufficiently distant from the awesome and unchallengeable might of the British Navy. White Plains was neither too close to Long Island Sound, nor too close to the Hudson River.
The year 1776 had begun relatively well for Washington. Under his leadership, the Continental Army had forced the British Army at Boston to evacuate by sea. This sucess seemed "heaven sent" – an affirmation of a righteous American Cause. Yet, only a few months later, a powerful British invasion force presented itself at Staten Island, threatening the massive fortifications Washington commanded at New York. In short order, the British inflicted a bitter defeat on Washington's forces at Brooklyn, and the depleted American Army narrowly managed to escape from Long Island to Manhattan. There, it was forced to abandon its fortifications in lower Manhattan and press northward, settling into a last ditch defensive position at Washington Heights (near the Westside Highway and the George Washington Bridge).
A minor victory at Morningside Heights (between the upper Westside and Harlem) served to restore some American confidence. Yet the American position, entrenched on the north end of Manhattan Island, was completely vulnerable, for it could be easily surrounded by the enemy. After several conferences with his senior officers, Washington decided that the greater part of his army must withdraw inconspicuously northward through Westchester County and set up a defensive position at White Plains.
Meanwhile, the British Army under General William Howe was moving a large portion of his force slowly, and fairly deliberately, up the edge of Long Island Sound. The shear size of his collected force was so great that it took time and great care to coordinate. His numbers are estimated at 30,000 – by some accounts, the largest amphibious invasion force in history up to that time.
Under General Howe's command was a large contingent of "Hessian" troops, a term applied to the German mercenary troops auxiliaried to the British Army. At the Battle of White Plains, it would be the Hessians who had the "honor" of launching the main attack against the right flank of the Americans on Chatterton Hill. It was their first significant opportunity for the Hessian force to "prove" itself before the assembled armies, and they managed to acquit themselves well in the military sense.
Washington was again forced to make an orderly withdrawal. The day went to the British and their allies, for the victory, in the eighteenth century meaning of the word, went to the combatant who remained in possession of the debated ground. However, Washington had, in a sense, won his own victory – through the survival of the Continental Army. It was October 28, 1776 – 235 years ago.
Yet, that did not end the fighting in the area of White Plains. In the next two days the American Army took up a new position slightly to the north of what was then the town of White Plains. A standoff between the Americans and their enemies ensued, neither side ready to commit to a mass attack.
On November 1, the face-off continued, and the combatants began an artillery exchange. The artillery batteries of both sides pounded away as the armies watched on. Perhaps each targeted the other's batteries, for in the midst of the action, as American General William Heath looked on, a Hessian artilleryman was decapitated by an American cannonball. "A shot from the American cannon at this place took off the head of a Hessian artillery-man," General Heath later recorded in his journal. "One of the artillery horses was also left dead on the field. What other loss they sustained is not known." Heath's journal was first published in 1798.
The military standoff continued until November 5th. Then, the enemy withdrew in the direction of Dobbs Ferry.
Did Washington Irving happen to see Heath's published journal at any time before writing the "Legend of Sleepy Hollow" in 1819? We do not know. Is it possible that he did? Yes. Is it likely? Maybe. Elsewhere in his writings, Irving relates that he first heard about the Headless Horseman from an African American mill hand at the old Sleepy Hollow Mill (or Carl's Mill) which stood near the intersection of the Pocantico River and Carl's Brook in northeast Sleepy Hollow. Apparently, by that time (about 1798) the Headless Horseman had become a neighborhood ghost.
But, how might this Hessian soldier have come to be buried in Sleepy Hollow? There is at least one dubious, unsubstantiated tradition informing us that while the two armies at White Plains waited each other out, the Hessian
soldier's grieving comrades picked up his headless body and carted it along with them as they made a foraging circuit near the Hudson River. There they entered the quiet and partly-deserted valley of Sleepy Hollow.
An old stone church stood there, reminiscent of the ones the Hessians remembered from their home country. Beside the rear of the church, quietly and without ceremony, they dug a grave and laid their friend's remains to rest beneath the dark loam. It was early November, and the trees had on their coats of autumn crimson. The air was crisp. The soldiers could not linger; they had orders and had to move on. Perhaps they took one farewell look over their shoulders as they drove their cart away.
That is a fanciful account of how the Hessian artilleryman might have been buried in the old burying ground. His head, so terribly shattered by a twelve-pound cannon ball, they had hastily buried on the field of battle in White Plains. ©