Remembering the Revolution · October 28, 1776
By late October 1776, the struggle for New York had carried George Washington’s army from Long Island to Manhattan and north into Westchester County. Each move surrendered ground while keeping the Continental Army beyond the enemy’s grasp. At White Plains, British commander General William Howe would have another opportunity to catch it.
The battle that followed became part of a difficult autumn for the American cause. It also acquired an unexpected association with a story published more than forty years later: Washington Irving’s The Legend of Sleepy Hollow. The connection is intriguing, though the history and the legend require different kinds of telling.
Why Washington Left Manhattan
September’s American victory at Harlem Heights had checked a British advance, but Washington’s army remained vulnerable on northern Manhattan. Howe could use the waterways around the island to move troops behind its defenses.
On October 12, British and German soldiers landed at Throgs Neck, but American resistance blocked their passage inland. Howe tried again farther up the coast, landing at Pell’s Point on October 18. Washington began moving most of his army toward White Plains, reaching his new headquarters on October 22.
The hills around White Plains offered defensive ground close to an American supply depot, allowing Washington’s troops to protect its provisions while they were moved farther north. Losing those supplies would compound the difficulties of another retreat.
October 28: The Assault Begins
The Bronx River created a weakness in the American position. Chatterton Hill stood across the water from Washington’s main defenses, leaving the troops there separated from much of the army.
When Howe advanced on October 28, American skirmishers contested his approach. Washington reinforced the hill with Continental troops under Alexander McDougall, joining the militia already there. Howe concentrated his attack on this exposed position.
About 4,000 British and Hessian soldiers, supported by 20 cannon, were assigned to the assault. American musket fire repelled the initial attack, but Hessian troops under Colonel Johann Rall struck the militia on the defenders’ far right.
As that flank gave way, the remaining defenders had to leave the hill, with Delaware soldiers helping to cover the withdrawal. Although the attackers had won the position, the fighting had not delivered Washington’s army into Howe’s hands.
What Howe’s Victory Achieved
Washington withdrew farther north on November 1. Howe subsequently turned back toward Manhattan, where Fort Washington’s American garrison remained despite the army’s departure.
The fort fell on November 16. The loss of Fort Lee across the Hudson followed days later, deepening the crisis as Washington’s forces retreated through New Jersey.
White Plains was a British victory with an incomplete result. Howe had forced the Americans from important ground, but Washington retained an army capable of continuing the war.
Was the Headless Horseman Killed at White Plains?
Readers of The Legend of Sleepy Hollow encounter an echo of the Revolution in its most feared figure: a Hessian horseman searching for his missing head.
In Irving’s story, first published in 1820, the rider is said to have been killed by a cannonball during the Revolutionary War. His body supposedly rests in the churchyard, and his ghost rides back toward the battlefield at night. Irving places his death in “some nameless battle.” He does not identify it as White Plains.
The White Plains connection comes through the local tradition associated with the tale. Scenic Hudson recounts the belief that the Horseman was a German soldier killed there and suggests that Irving may have heard stories about a headless Hessian buried near Sleepy Hollow. That is a possible influence on the fiction, rather than proof that a particular battlefield casualty became Irving’s character.
There were other possible influences, too. Stories of headless riders circulated in European folklore long before Irving wrote his version. He brought that supernatural figure into a recognizable Hudson Valley community, giving it local roads, family names, and a Revolutionary past.
Even within the story, the explanation remains unsettled. A shattered pumpkin and Brom Bones’s knowing laughter leave readers room to suspect a human trick behind Ichabod Crane’s terrifying encounter.
Another detail suits an October reading: Irving never says the chase takes place on Halloween. Its autumn setting and frightening events helped make it a seasonal favorite afterward. White Plains belongs to the documented history of October 1776; the Horseman belongs to the stories later told about a landscape still associated with the Revolution.
Bohea at Mount Vernon
Beyond the campaigns, Washington’s household records offer another connection to eighteenth-century life. Bohea was among the teas used at Mount Vernon, alongside varieties including Hyson and Imperial.
Our Colonial Bohea brings that household history to the table, a companion for an afternoon spent reading about the people and places of early America.
