American Revolutionaries and British Red Coats fought the Battle of White Plains on October 28, 1776. This is the day the headless horseman lost his head.
Gunpowder and smoke created a thick fog on Merritt Hill, where the colonists faced off against the British forces. As rifles were fixed and shots rang out, echoing their high-pitched tones through the forested landscape, the British were gradually, sneakily making their way up Hatfield Hill to launch a surprise attack.
Discovering their motives, an American lieutenant barked out an order: "Ready the cannons! The Red Coats are approaching from the left!"
On the lieutenant's cue, his men lit the fuse, sending the cannonball hurtling directly toward the 20 troops on horseback, and sending 19 of these men retreating back down the hill. The last unfortunate soul who didn't and who couldn't, fell to safety was a Hessian artilleryman - a board and brutish German mercenary hired by the British to fight the rebellious expatriates.
When the dust had settled, a gruesome sight littered the field: His head obliterated, the Hessian lay limp on the ground, blood and gore and chunks of gray matter scattered all around. Triumphant, the Americans marched forward into the next battle, clamoring over their victory to comrades who weren't there to witness the event themselves.
The new spread far and wide by way of drunken, gossiping mouths in the taverns. Rumor had it the Hessian and his horse had been placed in an unmarked grave a few miles away at the Old Dutch Church and, at night, you could feel the ground underneath shaking ever so slightly, as if the buried were trying to break free.
Three days of skirmishes passed, and on the third night, the gunfire ceased and the towns were silent. It was All Hallow's Eve, and an eerie aura hung in the air, whispered through the scrawled tree branches shedding their leaves. There was no moon that night, just pure darkness stretched across the sky like a sheet of black velvet.
After a long cold winter night, early in the New Year, a certain Dutchman left the tavern in Tarrytown and started walking to his home in the hollow nearby. His path led next to the old Sleepy Hollow cemetery where a headless Hessian soldier was buried. At midnight, the Dutchman came within site of the graveyard. The weather had warmed up during the week, and the snow was almost gone from the road. It was a dark night with no moon, and the only light came from his lantern.
The Dutchman was nervous about passing the graveyard, remembering the rumors of a galloping ghost that he had heard at the tavern. He stumbled along, humming to himself to keep up his courage. Suddenly, his eye was caught by a light rising from the ground in the cemetery. He stopped, his heart pounding in fear. Before his startled eyes, a white mist burst forth from an unmarked grave and formed into a large horse carrying a headless rider.
The Dutchman let out a terrible scream as the horse leaped toward him at a full gallop. He took to his heels, running as fast as he could, making for the bridge since he knew that ghosts and evil spirits did not care to cross running water. He stumbled suddenly and fell, rolling off the road into a melting patch of snow. The headless rider thundered past him, and the man got a second look at the headless ghost. It was wearing a Hessian commander's uniform.
The Dutchman waited a good hour after the ghost disappeared before crawling out of the bushes and making his way home. After fortifying himself with schnapps, the Dutchman told his wife about the ghost. By noon of the next day, the story was all over Tarrytown. The good Dutch folk were divided in their opinions. Some thought that the ghost must be roaming the roads at night in search of its head. Others claimed that the Hessian soldier rose from the grave to lead the Hessian soldiers in a charge up nearby Chatterton Hill, not knowing that the hill had already been taken by the British.
Every night, a brave soul or two would trek out to the the site to catch a glimpse of The Headless Horseman, some never to be seen again.
Whatever the reason, the Headless Horseman continues to roam the roads near Tarrytown on dark nights from that day to this.