Westchester County, New York and the Revolutionary War: The Battle of White Plains (1776)

The first Westchester deployment occurred in October, 1776, during the war’s bleakest phase. In March of that year, when the British were compelled to evacuate Boston, a feeling of guarded optimism briefly prevailed among the Americans. Hopes were soon crushed, however, by the disastrous American defeat at the Battle of Long Island in August. Washington’s long retreat from New York City began several weeks later, first into Westchester and eventually across New Jersey. During the New Jersey phase of the retreat, the British army was in hot pursuit, and observers judged the American cause to be near collapse. 

The Battle of White Plains might be viewed as a pause in the long retreat. Positioning his army on the hills around White Plains in late October, Washington decided to make a stand against British General William Howe, whose regiments were advancing from New Rochelle and Scarsdale. The southern anchor of Washington’s defensive line was at Chatterton Hill (also known today as Battle Hill), and that is where the line failed to hold. British and Hessian units charged up the hill from the Bronx River, and the first two or three waves were repulsed. But a superior enemy force finally drove the Continental troops from the hilltop. With the loss of Chatterton Hill, Washington was forced to pull back from the entire defensive line around White Plains. 

At the time, the defeat at the Battle of White Plains seemed to be another dismal episode in the collapse of Washington’s army. But events soon revealed a different reality. What would prove, in retrospect, to be most important about the Battle of White Plains was not the American defeat, but Washington’s ability to prevent envelopment by General’s Howe’s forces, withdraw his troops in good order, and preserve the army for a more propitious day. 

That day came soon enough: After retreat across the Delaware River into Pennsylvania, the Americans showed astonishing resilience and boldness in late December, 1776, and early January, 1777, when Washington re-crossed the Delaware into New Jersey and won dramatic victories at Trenton and Princeton. American morale, depressed during the long retreat, was given a huge boost.   

However, the British remained a determined enemy, and, over the subsequent months of 1777, the Americans saw defeat more often than victory. Then the tide of war turned again, when the British suffered a staggering defeat in October, 1777, at Saratoga, 30 miles north of Albany, at the hands of the American “Northern Army” and its commander, General Horatio Gates.

Since 1776, Congress had been asking France for a formal alliance against Great Britain, France’s traditional foe. The French government at first held back, assuming that the American uprising had little chance of success. Saratoga radically altered French opinion: It appeared that the American rebels might succeed after all! Paris signed a treaty of alliance with the United States in February, 1778, and dispatched a flotilla of warships to North American waters, under the command of Admiral Charles, comte de d’Estaing, to work in concert with Washington’s forces.