250 Years Ago, August 27, 1776: The Battle of Long Island

The Revolution nearly died on a Brooklyn battlefield. On August 27, 1776, roughly 20,000 British and German troops attacked Washington’s divided force of about 10,000 Americans on Long Island. The battle became the largest of the Revolution to that point.

Washington had received reports that 8,000 to 9,000 British troops landed at Gravesend Bay on August 22, but he still could not determine whether Long Island was the main target or a diversion against New York City. That uncertainty helped leave his left flank dangerously exposed.

Howe exploited it. During the night of August 26, several thousand British troops marched through the barely defended Jamaica Pass, guided by Loyalists. Around 9:00 AM on August 27, they struck the American rear while Hessians attacked from the front. The American left was being enveloped before many soldiers understood what was happening.

The fighting was fierce across Battle Pass and Battle Hill, where Continental troops resisted the British advance. Elsewhere, Americans were driven toward Gowanus Creek, a difficult, marshy crossing that became a desperate escape route. The battle was not one single clash, but a series of brutal engagements spreading across the Brooklyn Heights defenses.

Near the Old Stone House, Lord Stirling led a rear guard of roughly 400 Maryland and Delaware soldiers against a vastly larger British and Hessian force. The Marylanders made repeated attacks, drawing fire away from Americans retreating toward Gowanus Creek. The First Maryland lost 256 men killed or captured, an extraordinary sacrifice for a regiment that had about 1,100 men earlier that month.

Washington watched the desperate fighting and reportedly exclaimed, “Good God! What brave fellows I must this day lose!” American losses ultimately included about 300 killed and 1,097 captured. Major General John Sullivan and Lord Stirling were among the prisoners.

By August 29, Washington recognized that another fight could destroy the army. His generals unanimously advised retreat. Beginning late that night, roughly 9,000 Americans crossed the East River. John Glover’s Marblehead sailors and men from Salem operated the boats through the darkness. A heavy fog concealed the final withdrawal, and by morning the army was safely in Manhattan.

Washington’s ability to recognize when survival mattered more than holding ground became crucial throughout the war. Preserving the army bought time for Saratoga in 1777, the French alliance in 1778, and ultimately the combined American and French victory at Yorktown in 1781.

Washington lost Long Island. But he saved the army that would win our freedom.