The summer of 1776 was supposed to be the season when everything changed. On July 4, the delegates in Philadelphia had declared to the world that the thirteen colonies were no longer subjects of King George III, but free and independent states. The ink was barely dry when George Washington found himself staring across New York Harbor at the largest armada the British Empire had ever assembled. Thousands of redcoats and Hessians, backed by one of the most powerful navies in the world, were bearing down on a force of farmers, mechanics, and merchants trying to pass themselves off as soldiers. The Battle of Long Island, fought on August 27, would be the first great test of the new United States. It would also be the largest battle of the war. And it would end in disaster, a defeat so crushing that only a miracle kept the Revolution alive.
The British had been driven from Boston in March, a humiliation that stung General William Howe. He knew that Boston had been the wrong place to try to hold. Too many hills, too many angry patriots with muskets, and too few loyalists. New York was different. The harbor was one of the finest in the world. The Hudson River was a natural highway that cut straight into the heart of the colonies. Loyalists were plentiful, ready to welcome the King’s soldiers. From New York the British could strike north to Albany, east into New England, or south into New Jersey. Howe was confident this would be the place to end the rebellion once and for all.
Washington saw it too. He marched his 19,000 men into the city, but he did not like what he saw. The place was a trap. Whoever controlled the sea controlled New York, and the British navy was everywhere. His men were green and jittery, a patchwork of short-term militia and half-trained recruits. He tried to put on a bold face, but in letters to Congress he confessed doubts. He had no illusions about how precarious the situation was. Worse still, Congress insisted New York be defended. Losing it without a fight would be politically unthinkable. So Washington had no choice but to dig in and prepare to meet Howe’s army head-on.
The British arrived in force in July. Thirty two thousand troops crowded onto Staten Island, the largest expeditionary force Britain had ever sent overseas. Loyalist families poured out to greet them, offering food, shelter, and intelligence. It was an overwhelming display of power. From Manhattan, Washington’s men could see the forest of masts across the water, hear the beat of drums, and feel their stomachs turn at the sight. This was not a skirmish with a few hundred redcoats. This was the real thing.
Before the shooting started, Howe tried diplomacy. He and his brother, Admiral Richard Howe, carried the title of peace commissioners and hoped to bring the rebels back to the fold without more bloodshed. They offered to meet Washington, but addressed their letter simply to “George Washington, Esquire.” Washington refused to accept it. If they wanted to negotiate, they would have to recognize his title as General. The Howes would not. The British position was clear: only complete submission would end the rebellion. Washington knew then that the sword, not the pen, would decide the issue.
On August 22, Howe made his move. Twenty thousand troops splashed ashore at Gravesend Bay on Long Island. Along with redcoats came 5,000 Hessians, mercenaries from the German states, along with Loyalists and even some formerly enslaved men promised freedom in return for service. Washington believed it might just be a diversion. He expected the main blow to fall on Manhattan. He sent reinforcements to Long Island, but not enough. Command there was unsettled. Nathanael Greene, one of his ablest generals, fell sick. John Sullivan replaced him, then Israel Putnam. The Americans were stretched thin, poorly led, and badly outnumbered.
The defense hinged on a series of wooded hills known as the Guan Heights. Three main passes cut through them, and American troops guarded each. But there was a fourth, Jamaica Pass, and here the defense was laughable. Only five militia officers patrolled it. Five men to cover a road wide enough to move an army. Local Loyalists told the British exactly where to find it. General Henry Clinton saw his chance.
The American army on Long Island numbered about ten thousand. Washington had positioned roughly four thousand across the heights. Among them were some of the best troops he had, including the 1st Delaware Regiment and the 1st Maryland Regiment, known for their sharp drill and fashionable uniforms. They were sometimes mocked as dandies, but they were also some of the steadiest men in the ranks. Against them the British arrayed a host that dwarfed their numbers, commanded by Howe, Clinton, Cornwallis, Grant, and the Hessian general von Heister.
On the night of August 26, Clinton led ten thousand men on a secret march through Jamaica Pass. At two in the morning they captured the five American patrols without firing a shot. As dawn broke, they were in position to fall on the American rear. Meanwhile, General James Grant launched a diversionary attack on the American right at the Gowanus Road. Lord Stirling, commanding about 1,600 men, stood his ground. Fierce fighting raged around Battle Hill. Stirling believed this was the main attack, and for four hours his men held their line. It was brave, stubborn, and utterly in vain.
At nine o’clock the trap snapped shut. Von Heister’s Hessians stormed Battle Pass, blasting the American defenders with cannon before charging in with bayonets. At the same time Clinton’s column struck from behind. General John Sullivan’s men were engulfed. Sullivan himself was taken prisoner. Panic spread. Men threw down their muskets and ran for the safety of Brooklyn Heights. The right flank under Stirling was suddenly cut off. Behind them lay the swampy Gowanus Creek, eighty yards wide and nearly impassable. In front of them were thousands of redcoats and Hessians.
Stirling made his decision. He ordered most of his men to cross the creek, slogging through mud and water to reach the fortifications beyond. With him remained about 270 Marylanders under Major Mordecai Gist. They would cover the retreat. What followed was one of the most desperate and heroic episodes of the war. Again and again, the Marylanders charged the British near the Old Stone House, a sturdy farmhouse that anchored Cornwallis’s position. Outnumbered nearly ten to one, they attacked six times. Each time they were thrown back, and each time they re-formed and went in again. Washington, watching from a distance, is said to have cried out, “Good God, what brave fellows I must this day lose.”
The sacrifice was terrible. Of the Marylanders, 256 were killed outright. Only a handful made it back. But they bought precious time. Thanks to their stand, the bulk of Stirling’s command and much of the American army escaped into the Brooklyn Heights fortifications. The Maryland 400, as they came to be called, earned immortality. Their blood marked the ground where they fell, and their stand gave Maryland the proud title of “The Old Line State.”
By the end of the day, Washington’s army was in shambles. Thousands had been captured. The survivors were penned in on Brooklyn Heights, their backs to the East River. Howe had them exactly where he wanted them. One more assault could have ended the rebellion in a single blow. But Howe hesitated. He remembered the slaughter at Bunker Hill and was wary of storming entrenched Americans. He believed he had them trapped and chose to dig in and prepare a siege. His officers, Clinton especially, fumed at the lost opportunity.
Washington knew the game was nearly up. His army was surrounded, the river at their backs, and the British navy ready to cut off escape. But then fortune, or Providence, intervened. On August 28 a heavy storm blew in, grounding the British fleet and preventing it from sealing the East River. On the night of August 29, Washington put his plan into action. Under cover of darkness, Colonel John Glover’s Marblehead regiment, made up of New England fishermen, manned the boats. In absolute silence they ferried men, horses, cannon, and supplies across the river to Manhattan. At one point the wind shifted and threatened to expose the retreat, but then a dense fog rolled in, cloaking the operation. By dawn on August 30, the entire army, nearly nine thousand strong, was gone. The British advanced only to find empty trenches. Washington had pulled off one of the most remarkable retreats in military history.
The cost of the battle was staggering. About two thousand Americans were killed, wounded, or captured. British and Hessian losses were fewer than four hundred. Thousands of prisoners were crammed into rotting ships anchored in New York Harbor. Disease and starvation ravaged them. More Americans would die in those prison hulks than on the battlefield. The Revolution’s first major battle had ended in catastrophe.
The British celebrated their triumph. They occupied New York and Long Island and would hold them for the rest of the war. Washington’s army reeled, retreating north through Manhattan, fighting a sharp action at Harlem Heights, then falling back to White Plains. Fort Washington fell, then Fort Lee. By the end of the year, the Continental Army was fleeing through New Jersey, reduced to a shadow of its former self. Morale collapsed. Men deserted in droves. Many thought the Revolution was finished.
And yet it endured. The sacrifice of the Marylanders at the Old Stone House bought time. Washington’s retreat preserved the army. The fog over the East River gave the cause one more chance. The lesson was clear. There would be no quick victory. Independence would be won only by outlasting the empire, by refusing to quit even in the face of disaster.
The legacy of the Battle of Long Island is written not in triumph but in survival. It is remembered in the monuments of Brooklyn, from the Prison Ship Martyrs’ Monument to the Maryland Memorial in Prospect Park. The Old Stone House still stands, a witness to the courage of the men who fell before it. And it is remembered in the history of Maryland, whose soldiers became known as the Old Line, immortals whose sacrifice helped keep the flame of independence alive.
Washington lost the battle, but he saved the war. The Continental Army staggered, bloodied but breathing. The dream of independence was not crushed on the fields of Long Island. It lived to fight another day, carried forward by men who learned in that awful summer that freedom would not come cheaply, but that it was worth the cost.
DAVE DOES HISTORY 
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