Chatterton Hill

A War of Maneuver

The campaign of conquest in New York involved both land and sea maneuvers. In the late summer of 1776, the British landed on Long Island and pushed the Continental Army back to the Island of New York (Manhattan), where they faced a stalemate at Harlem Heights.

After the fighting at Harlem Heights, General George Washington’s Continental Army continued to hold onto upper Manhattan. By mid-October, Washington learned that the British were again on the move, planning to land in what is now Westchester County and surround him. Washington moved most of his forces across King's Bridge, leaving a garrison of about 1,500 men under General Nathanael Greene to hold Fort Washington. 

The British landed at Pell’s Point, and a cat-and-mouse game ensued as their advance was slowed by a series of brave American riflemen's holding actions. Eventually, Washington decided to stand against the British, who were pushing west toward the North (Hudson) River, which would cut Washington off from his supply line. He established a defensive position in the hills of White Plains, where the terrain would favor a defensive stand. The armies were roughly evenly matched, though Washington’s force of 14,500 men was far less trained and equipped than Howe’s force of 13,00 British regulars and Hessian professionals.

Gen George Washington's initial overlook
of Chatterton Hill gave the British an opportunity

A Place of Battle

Present-day White Plains offers few reminders of the American Revolution. In this Westchester County suburb of New York, office buildings and a bustling downtown area are surrounded by residential neighborhoods. It was in White Plains that the youthful version of your author took the road test for his driver’s license. At the time, I, like the thousands who live and work in the city, had no idea that nearby was once a bitterly contested battlefield.

Washington's HQ was at the Elijah Miller House in North White Plains

Washington Decides to Stand His Ground

Col Joseph Spencer

By October 28, 1776, Washington’s forces occupied a crescent-shaped three-mile line stretching from the Bronx River to the east to the Croton River to the west. Washington set up his headquarters at the Elijah Miller House in North White Plains and chose a defensive position fortified with two lines of entrenchments. The trenches were dug on elevated terrain, with the right flank protected by swamps near the Bronx River and steep hills further back serving as a retreat. Divisions under Israel Putnam and William Heath were positioned on the right and left flanks. Washington himself held the center. Beyond the right flank of this line was Chatterton Hill, which dominated the ground over which the British would have to advance. Interestingly, Washington initially only posted some militia companies under Connecticut Colonel Joseph Spencer to guard this strategic piece of terrain. He would soon need to send more troops.

White Plains

Sir William Howe

Around mid-morning, news reached Washington that the British were approaching in two columns along the East Chester Road. When they arrived, the British army deployed in an open area about a mile in front of the American line, where their formation was clearly visible to the defenders. Was this an attempt by British commander Sir William Howe to intimidate the Americans and lower their morale? Who knows what the delay cost him in real terms. Could another Bunker Hill be on the horizon? That had always been Howe’s fear since he played a key role in Britain’s costly victory outside Boston. Combined with his hope for reconciliation with the rebels, it seemed to hold him back from launching a massive attack that might have cost both sides greatly.

Seize the Good Ground

This time, Howe made a series of smart decisions. He scanned the American defenses ahead of him and realized he had enough manpower and firepower to launch a frontal assault. However, Howe quickly recognized there was another option - a way to move Washington without causing a bloodbath. The lightly guarded high ground known as Chatterton Hill, just to Washington’s right, is the key to the battlefield. Taking control of that would secure victory over the Americans. Howe discussed with his staff and decided that the main attack would target Chatterton Hill, while the rest of the army would keep the main American line busy. He began preparing to assault the hill, assigning the task to General Alexander Leslie (see the Yankee Doodle Spies blog on Leslie), with two British infantry regiments supported by Hessian troops. Soon, a fierce but inconclusive battle would unfold.

View of White Plains from Chatterton Hill

Finally, Washington recognized the danger he faced if the British seized the key terrain. He hurried to reinforce the heights with another 2,000 men under Colonel Joseph Reed. The critical outpost on Chatterton Hill was eventually held by about 4,000 men under Colonel Alexander McDougall. His force included two New England militia regiments under Colonel Rufus Putnam and Spencer's men. Even as Howe and his staff conferred, his Hessian artillery began firing on the hilltop. A force of 1500 skirmishers under Colonel Joseph Spencer was positioned along the front. The American defenses seemed strong. But when the British finally launched their attack, they quickly pushed aside the skirmishers, who scattered before the advancing troops. However, the arrival of McDougall and his brigade helped rally the defenders, and a defensive line was formed, with the militia on the right and the Continentals along the top of the hill.

Washington rushes reinforcements to the heights

Although he now faced a well-orchestrated onslaught, McDougall made a stubborn defense of it. He managed to hold Leslie’s column at the ford, repelling several attempts to cross the Bronx River. In response, Howe ordered more men, while a force of Hessian infantry under Colonel Johann Rall, supported by British dragoons, moved on the American right flank. The Hessians managed to cross the river and charge up the steep slope, but the determined and well-positioned Americans drove them back. Not to be outdone by the Rebellen, Rall rallied his men and organized a second attack with additional firepower. The artillery fired at the Americans defending the crest of the hill, causing the militia troops to run. However, despite the intense barrage, the Continentals stubbornly held on until the Hessians finally turned their right flank, forcing them back as well.

Hessians advancing under fire

A Timely Retreat, An Untimely Pause

With his flank exposed and crumbling, Washington ordered a retreat, and the Americans withdrew from the hill. Unfortunately for the British, William Howe stays true to form and does not follow up on his success with a vigorous pursuit that might have destroyed the Continental Army and ended the war. Instead, he waits for reinforcements from the rest of his army and simply bivouacs his men on Chatterton Hill. This gives Washington time to move his army to stronger positions at nearby North Castle a few days later. Although the Americans lost the Chatterton Heights along with approximately one hundred thirty killed and wounded, taking the heights cost Howe around two hundred fifty irreplaceable British and Hessian troops killed and wounded. In a sense, Howe came out ahead in that Washington ultimately evacuated New York and abandoned the defenders of Fort Washington to their ultimate demise. But the war of posts would now evolve into a war of maneuver, this time across the Jerseys.

A  Halloween Connection?

Little remembered in history, the action at Chatterton Hill has a link to American folklore and the spooky celebration of Halloween. Washington Irving’s story, The Legend of Sleepy Hollow, and the film, Sleepy Hollow, focus on the haunting by a “Headless Hessian Horseman.” According to some accounts, Irving based the story on an incident during the Battle of White Plains when a Hessian soldier, decapitated by a cannon shot on Chatterton Hill, roams the Westchester night seeking vengeance. So, Chatterton Hill leaves a legacy of little military importance but an eerie contribution to American folklore… oh yes, and your humble author passed his road test - first time.

A Hessian's death at Chatterton Hill may have inspired
one of America's earliest legends - Sleepy Hollow