28 October 1776. White Plains, New York. George Washington was aware of General William Howe’s advance on his army. He had already sent some of his officers on reconnaissance missions to discover the British position and determine how soon they might reach White Plains. The Continental Army arrived at White Plains on October 23, ahead of Howe’s army. Washington chose a defensive position that he fortified with two lines of entrenchments. The trenches were situated on raised terrain, protected on the right by the swampy ground near the Bronx River, with steeper hills further back as a place of retreat. The American defenses were three miles long. Beyond that, across the Bronx River on the right, was Chatterton’s Hill, which commanded the plain over which the British would have to advance. Washington sent Maryland and Delaware forces, some Connecticut regimentals and some militia to Chatterton’s Hill to join an outpost held by Colonels Alexander McDougall and Rufus Putnam. There approximately 2,000 men began constructing fortifications.
On the morning of October 28, 1776, Howe ordered his entire force, 13,000 strong, forward to White Plains to attack the American lines. Howe took General Henry Clinton’s advice and proceeded in several columns. Washington ordered his officers holding the lines—William Heath, John Sullivan, and Charles Lee to go forward and do the best they could. Then, Washington called for a detachment of 1,500 men under General Joseph Spencer to confront the British vanguard. The detachment crossed the Bronx River and waited behind stone walls for the enemy. They became engaged with the Hessians, pouring a destructive fire into their ranks until they found that they were about to be flanked. The Americans retreated across the river and ascended Chatterton’s Hill.
Howe detached several thousand of his men and twelve pieces of artillery to attack Chatterton’s Hill. The British attack was organized with Hessian regiments leading the assault. Colonel Johann Rall was to charge the American right, while a Hessian battalion under Colonel Carl von Donop was to attack the center. When they reached the river, British grenadiers charged across and pressed up the steep and heavily wooded hill. They became targets of their own artillery which had ignited the dry autumn leaves and branches. The Hessians followed charging through the burning fields. They held their cartridge boxes above their heads to keep them from exploding.
The Americans fired canister and grape into the oncoming enemy. The Royal Artillery responded with solid shot. The Americans repelled the first wave of attack as they poured musket fire into the approaching enemy. Rall’s Hessians rallied and taking heavy casualties, fought up the southern side of the hill. Rall’s charge scattered the militia and they “fled in confusion,” Colonel John Haslet of the Delaware troops reported. This exposed the American right flank.
The British pelted the Marylanders and the Delaware Regiment with a “very heavy fire of their artillery and musquetry for about half an hour.” Reinforcements arrived, but the Marylanders and Delaware men were forced to withdraw. “The Americans overpowered by their numbers, were compelled to save themselves, as best they could,” recalled Marylander Captain Samuel Smith. Washington ordered a fighting withdrawal with the 1st Delaware Regiment guarding the rear. The Continental Army continued their retreat to North Castle, New York. Both sides suffered significant casualties. The high price (in casualties) the British army paid for the hill was enough to discourage further aggression on General Howe’s part.
"White Plains, 1776" painting by Graham Turner