Battle of Long Island

The Battle of Long Island on August 27, 1776 was the largest battle of the entire Revolutionary War and one of the most dangerous moments for the American cause. The British had assembled 32,000 soldiers and sailors supported by 400 ships. Washington, with only 23,000 men, attempted to defend Brooklyn Heights on western Long Island. His defenses centered on a line of hills — the Heights of Guan — with four passes, three of which Washington guarded. The Jamaica Pass on the far left was left unguarded, thought too distant to be threatened. This proved fatal.

On the night of August 26-27, Henry Clinton led 10,000 men on a wide flanking march through the Jamaica Pass. Guides provided by a local Loyalist led the column through, and they captured the five American scouts without raising an alarm. At dawn the flanking force emerged behind the American position while Hessians and British regulars attacked frontally. The American position collapsed. The Maryland 400 — a regiment that charged British lines six times in a desperate rear-guard action — became legendary for their sacrifice allowing comrades to escape.

Washington's entire army was trapped against the East River with Howe's forces in front and the British Navy behind. The situation appeared hopeless. But Howe chose not to launch an immediate assault, beginning siege operations instead. On the night of August 29-30, Washington executed one of history's most brilliant retreats. Under cover of a fortunate fog, 9,000 men with all their equipment were ferried across the East River in rowboats. By dawn every American soldier was in Manhattan.

The defeat cost roughly 2,100 killed, wounded, and captured, but the army survived. It demonstrated that Washington, despite tactical defeat, could command with extraordinary skill under extreme pressure. The survival of the Continental Army at Long Island is considered one of the most important moments of the entire war.