The Origin of the Headless Horseman and the Battle of White Plains — Hidden History

The Battle of White Plains took place on October 28, 1776. After British forces captured a key position on the west side of White Plains, the Americans were forced to retreat. According to legend, a Hessian soldier fighting for the Britsh was killed during the battle and returned as the legendary “Headless Horseman of Sleepy Hollow.”

The Headless Horseman Pursuing Ichabod CranePhoto byWikimedi

Americans Win the Battle of Harlem Heights

After British forces took control of New York City on September 15, General George Washington was forced to move north to Harlem Heights with the Continental Army. British forces, led by General William Howe, attacked on September 16, but the Americans held their ground and won the Battle of Harlem Heights.

British Forces Delayed at the Battle of Pell’s Point

A month later, Howe tried to flank Washington at Harlem Heights. His plan was to attack Washington from the east and push him out of Harlem Heights to the Hudson River. If that happened, then the Continental Army would be trapped between Howe’s army and the British Navy, which controlled the Hudson. Howe tried on October 12 but was pushed back at Throggs Neck.

On October 16, Washington and his officers decided to abandon their positions on Manhattan Island, except Fort Washington, and move north to White Plains.

Two days later, on October 18, the British landed at Pell’s Point. This time, American forces were unable to keep the British from landing, but they were able to delay them. A small force of American troops, led by Colonel John Glover, fought bravely, against overwhelming numbers, long enough to force Howe to pause his advance on White Plains.

The Battle of White Plains Historical MarkerPhoto byHistorical Marker Database

American Forces Withdraw to White Plains

Over the next 10 days, the Americans moved to White Plains while the British slowly advanced in that direction. Once the Continental Army was at White Plains, they dug entrenchments and prepared for the British attack. The American line stretched from Purdy Hill, near the Bronx River, west to Chatterton’s Hill, on the edge of White Plains. At New Rochelle, Howe was joined by around 8,000 Hessian troops under the command of Wilhelm von Knyphausen. Then Howe moved his army to Scarsdale, New York, and prepared to attack Washington.

The Two Armies at White Plains

On October 28, Howe advanced toward White Plains. On his right was General Henry Clinton, and on his left was General Leopold de Heister. At White Plains, Washington commanded the center, General Israel Putnam was on his right, and General William Heath was on his left.

The Battle of White Plains

Howe sent Clinton and de Heister forward. They were engaged and delayed by Americans under the command of Joseph Spencer. The British were able to push forward and Spencer and his men withdrew to the safety of Chatterton’s Hill. American forces on the hill covered Spencer and his men as they retreated. From that point on, the hill was the focal point of the Battle of White Plains.

Washington sent reinforcements to dig entrenchments and prepare for a British attack. After a short break in the fighting, Howe had his artillery open fire on the hill and sent an assault force of around 4,000 men against the Americans. The Americans fought off the first assault, which was against the left side of their lines.

However, Hessian troops and British dragoons attacked the right side of the line, which was defended by inexperienced militia. The militia on that side of Chatterton’s Hill panicked and fled, which forced General Alexander McDougall to order a retreat. By 5:00 that afternoon, the battle was over, and the British were in control of the hill.

Although sporadic fighting continued over the next week, the Battle of White Plains was essentially over.

The Legend of the Headless Horseman

The “Headless Horseman,” also known as the “Galloping Hessian,” is the villain in Washington Irving’s short story “The Legend of Sleepy Hollow.” The traditional explanation for the Horseman is he is a Hessian soldier who was decapitated by an American cannonball at the Battle of White Plains.

Washington IrvingPhoto byWikimedia

Irving’s story is set in 1790 near Tarrytown, New York. It tells the story of a schoolmaster, Ichabod Crane, who runs the local school. Crane becomes infatuated with Katrina Van Tassel, the daughter of a wealthy Dutch farmer. However, Crane has a competitor for Katrina’s affections—Abraham “Brom Bones” Van Brunt.

One night, the Van Tassels hold a harvest party. Both Crane and Van Brunt attend. During the festivities, Van Brunt tells the story of the local legend, the fearsome “Headless Horseman,” who is buried in the cemetery at the Sleepy Hollow church.

Near the end of the night, Crane asks Katrina to marry him, but she declines.

Historical marker near the Sleepy Hollow cemetery.Photo byHeirloom Art

Crane borrows a horse named “Gunpowder” and starts the ride home through the darkness. As he nears the spot where Major John André, the famous British spy who conspired with Benedict Arnold, was captured, he begins to lose his nerve.

“In the dark shadow of the grove, on the margin of the brook, he beheld something huge, misshapen and towering. It stirred not, but seemed gathered up in the gloom, like some gigantic monster ready to spring upon the traveller.”

Crane shouts, “Who are you?” He receives no response.

According to the legend, Crane knows he will be safe if he crosses the bridge near the church. The Horseman cannot follow him any further.

He makes a mad dash for the bridge, and the mysterious horseman gallops alongside him.

“An opening in the trees now cheered him with the hopes that the church bridge was at hand. The wavering reflection of a silver star in the bosom of the brook told him that he was not mistaken. He saw the walls of the church dimly glaring under the trees beyond. He recollected the place where Brom Bones’s ghostly competitor had disappeared.”

“If I can but reach that bridge,” thought Ichabod, “I am safe.”

The Horseman pursues Crane.Photo byVisit Sleepy Hollow

“Just then he heard the black steed panting and blowing close behind him; he even fancied that he felt his hot breath. Another convulsive kick in the ribs, and old Gunpowder sprang upon the bridge; he thundered over the resounding planks; he gained the opposite side; and now Ichabod cast a look behind to see if his pursuer should vanish, according to rule, in a flash of fire and brimstone.”

“Just then he saw the goblin rising in his stirrups, and in the very act of hurling his head at him. Ichabod endeavored to dodge the horrible missile, but too late. It encountered his cranium with a tremendous crash,—he was tumbled headlong into the dust, and Gunpowder, the black steed, and the goblin rider, passed by like a whirlwind.”