Chatterton Hill

A War of Maneuver

The campaign of conquest in New York was one of maneuver on land and sea. During the late summer of 1776, the British landed on Long Island and forced 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 on to 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 the Kings Bridge, leaving a garrison of some 1,500 under General Nathanael Greene to hold Fort Washington. The British landed at Pell’s Point and there began a cat and mouse game as the British advance was slowed by a series of holding actions by valiant American riflemen. Eventually, Washington determined on a stand against the British, who were pushing west towards the North (Hudson) River that would cut Washington off from his supply line. He established a defensive position in the hills of White Plains, where the terrain might favor a defensive stand. The armies were about evenly matched, although Washington’s force of 14,500 men was in no way as well trained or equipped as 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 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 between the Bronx River to the east and the Croton River to the west. Washington established his headquarters at the Elijah Miller House in North White Plains and chose a defensive position that he fortified with two lines of entrenchments. The trenches were dug on raised terrain, their right flank protected by the swamps near the Bronx River, and steep hills further back as a place of retreat. Divisions under Israel Putnam, William Heath are placed on the right and left flanks. Washington himself held the center. Beyond the right flank of this defensive line lay Chatterton Hill, which dominated the ground over which the British would have to advance. Curiously, Washington initially had posted only some militia companies under Connecticut Colonel Joseph Spencer to guard this obvious piece of key terrain. He would soon have to send more.

White Plains

Sir William Howe

Around mid-morning, word reached Washington of the British approaching in two columns along the East Chester Road. When they arrived, the British army deployed in an open area about one mile in front of the American line where their array was quite visible to the defenders. Was this an attempt at intimidation by the British commander, Sir William Howe to subvert American morale? Who knows what the delay cost him real terms. Could another Bunker Hill be in the offing? This was always Howe’s fear since he played a key role in Britain’s Pyrrhic victory outside Boston. That coupled with his hope of reconciliation with the rebels seemed to hold him back from a massive attack that could cost both sides.

Seize the Good Ground

This time Howe made a series of good decisions. He scanned the American defenses to his front. He realized he had the manpower and firepower to make a frontal assault. But Howe quickly recognizes there is another way - a way to move Washington without a blood bath. The lightly defended high ground known as Chatterton Hill over on Washington’s right is the key to the battlefield. Seize that and the Americans are bagged! Howe conferred with his staff and decided the main attack would go against Chatterton Hill while the rest of the army kept the main American line occupied. He began preparations to storm the hill, giving the attack to General Alexander Leslie (See the Yankee Doodle Spies blog on Leslie), with two British infantry regiments supported by a force of Hessians. Soon a bloody if inconclusive fight would ensue.

View of White Plains from Chatterton Hill

At last, Washington realized the danger he faced if the British seized the key terrain. He rushed to reinforce the heights with another 2,000 men under Colonel Joseph Reed. The critical outpost on Chatterton Hill eventually would be held by some 4,000 men under the overall command of Colonel Alexander McDougall. His force would include two New England militia regiments under Colonel Rufus Putnam and Spencer's men. Even as Howe and his staff conferred, his Hessian artillery opened fire on the hilltop. A force of 1500 skirmishers under Colonel Joseph Spencer is arrayed along the front. The American defenses seemed sound. But when the British finally launch their attack, they quickly brushed aside the skirmishers, who scattered before the attackers. But the arrival of McDougall and his brigade helped to rally them, and a defensive line was established, with the militia on the right and the Continentals arrayed along the top of the hill.

Washington rushes reinforcements to the heights

Although he now faced a well-orchestrated onslaught, McDougall made a game defense of it. He managed to pin Leslie’s column at the ford, repulsing several attempts to cross the Bronx River. In response, Howe ordered up more men while a force of Hessian infantry under Colonel Johann Rall, supported by British dragoons, moved on the American right flank. The Hessians manage to ford the river and charge up the steep slope, but the desperate and well-positioned Americans drove them back. Not to be outdone by die Rebellen, Rall rallied his men and organized a second attack with more firepower. The artillery fired up the Americans defending the crest of the hill, which sent the militia troops to run. But 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 withdraw 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 awaits reinforcements from the rest of his army and simply bivouacs his men on Chatterton Hill. This gave 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 someone hundred thirty killed and wounded, taking the heights cost Howe some 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 morph into a war of maneuver, this time across the Jerseys.

A  Halloween Connection?

Little remembered in history, the action at Chatterton Hill has a connection to American lore and the eerie celebration of Halloween. Washington Irving’s story, The Legend of Sleepy Hollow, and the film, Sleepy Hollow, are centered on the haunting by a “Headless Hessian Horseman.”  By 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