On August 27th, 1776, George Washington stood on the heights of Brooklyn and watched his army being destroyed. Through his spyglass he could see the Continental soldiers—the only army America had—caught in a trap, pressed against a tidal marsh by thousands of British regulars and German Hessians. Independence had been declared just fifty-two days earlier. In the span of a morning, it was dying on a battlefield in New York.

Fewer than four hundred men were left to stop it. They were young farmers and merchants from Maryland, most barely past boyhood, and they were about to be ordered into a suicide charge against a British force ten times their size. The road to that desperate moment began more than a year earlier, on April 19th, 1775, when the first shots of the American Revolution rang out at Lexington and Concord. What started as a British raid on colonial weapons stores spiraled into open warfare.
Two months later came the carnage of Bunker Hill. The British won the field but paid a devastating price—over a thousand casualties, the costliest engagement of the entire war. The colonists had proven they could stand and fight against the most powerful army in the world. For nearly a year, Washington besieged the British in Boston.
Finally, in March of 1776, British commander General William Howe was forced to evacuate, sailing north to Nova Scotia to regroup. Washington had won his first major victory, but he knew it was far from over. The British would return. The question was where.
Washington predicted New York. The city’s deep-water ports could supply and anchor the entire British fleet. Control New York, and you controlled the Hudson River, splitting New England from the rest of the colonies. Sever it, and the rebellion would be cut in half.
In April of 1776, Washington relocated his fledgling Continental Army and began fortifying New York. But New York presented problems Boston never had. The terrain was a nightmare—islands, rivers, and waterways everywhere—and the Americans had no navy to defend them. The British fleet could strike from any direction.
Worse, New York was a loyalist stronghold. Nearly half the population supported the crown. Loyalists in the countryside intercepted vital messages and captured supplies. Spies were everywhere.
Trust was scarce. Washington assumed the British would strike Manhattan directly, and on that assumption he made a critical mistake. He divided his army, scattering 19,000 men across multiple positions. The bulk stayed on Manhattan to defend the city.
A smaller force of just 4,500 men was sent across the East River to Long Island. In early July, Howe returned. A massive British armada, growing to over three hundred ships, arrived off Staten Island—the largest expeditionary force ever assembled by the British Empire. Packed aboard were more than 32,000 soldiers: British regulars, Scottish Highlanders, and thousands of German Hessian mercenaries.
Leading them were some of Britain’s most experienced commanders, including Lord Cornwallis and Sir Henry Clinton. Two days later, on July 4th, the Continental Congress in Philadelphia signed the Declaration of Independence. When news reached New York, Washington gathered his troops to hear the declaration read aloud in the public square. The men cheered, bells rang, and for a brief moment anything seemed possible.
That night a mob descended on the massive equestrian statue of King George III. They tore it down, cut off the king’s head, and mounted it on a spike outside a local tavern. The rest of the statue was melted down and cast into musket balls—the tyrant king transformed into ammunition for his own destruction. Across the harbor on Staten Island, the British officers watched the bonfires and heard the distant cheers.
They weren’t worried. They knew what Washington was trying to hold together. The Continental Army was barely an army at all. Most were militia farmers and tradesmen who had never fired a shot in anger.
They drilled poorly, if they drilled at all. Desertions were constant. Disease tore through the camps—dysentery, smallpox, typhus. Men were dying faster than they could be replaced.
Worse, the army was fractured by colonial rivalries. Massachusetts men wouldn’t take orders from Virginia officers. New Yorkers distrusted New Englanders. Regiments bickered over supplies, rank, and territory.
But the First Maryland Regiment was different. While most Continental soldiers drilled poorly and fought in rags, the Marylanders were well-paid, well-trained, and looked like professionals. They wore crisp uniforms—blue coats with red facings—and hunting shirts for field dress. They carried polished muskets and something almost no other American unit had: bayonets, real steel that could turn a musket into a spear in close combat.
They were young, averaging barely twenty-one years of age. Sons of wealthy merchants, apprentice clerks, a few plantation owners, recruited mainly from the port city of Baltimore and the colonial capital of Annapolis. When they joined Washington’s army in New York, they were mockingly called “the Macaronis”—dandies, pretty boys in fancy uniforms. But to the Hessians, the sight of their hunting shirts meant one thing: American sharpshooters.
Seven hundred strong, the Maryland regiment was commanded by Colonel William Smallwood. But Smallwood was unexpectedly called away to oversee a court-martial, leaving command to fall to General William Alexander, who styled himself Lord Stirling after a disputed Scottish title. Major Mordecai Gist, a Baltimore native, led the regiment in the field. Positioned on Long Island, these elite troops anchored the American right flank near Brooklyn.
They had no idea what was coming. On August 22nd, the British made their move—but not toward New York. Four thousand British troops under Sir Henry Clinton and Lord Cornwallis landed unopposed on Long Island. Within hours, 15,000 troops were ashore alongside forty pieces of artillery.
Hundreds of loyalists swarmed the beach to greet them as liberators. Word reached Washington in New York, but the report was wrong. His scouts estimated only 8,000 troops had landed. Convinced this was a feint, Washington believed the real attack would come at Manhattan.
He sent a meager 1,500 reinforcements to Brooklyn, bringing American forces on Long Island to just 6,000 men. The American defense was centered across the Gowanus Heights, a 150-foot ridge of hills blocking the direct route to the fortifications at Brooklyn. Three main passes through the heights—Gowanus, Flatbush, and Bedford—were heavily guarded. By stationing men on the higher ground, they could inflict heavy casualties on the British before falling back to the main defenses.
General Israel Putnam commanded Brooklyn Heights. Lord Stirling and his Marylanders, along with the First Delaware Regiment, held the American right at Gowanus Pass with 1,600 men. Major General John Sullivan, commander of the force on Long Island, held the center with 1,500 men. Colonel Samuel Miles and his Pennsylvania Rifle Regiment held the hill to the east with around 500 men.
But there was a fourth route: the Jamaica Pass, far to the east. A local loyalist informed General Clinton of the route, patrolled by just four militia officers on horseback. Clinton saw the opportunity. Howe approved.
On August 26th at 9:00 p. m. , under cover of darkness, 10,000 British troops began a night march toward the Jamaica Pass. It was one of the most audacious gambles of the war.
The column stretched over two miles, an advanced party led by Clinton, followed by Cornwallis and Howe himself. They left their campfires burning behind them to deceive the Americans. If discovered, the whole operation would collapse—10,000 men strung out in the darkness on a narrow country road, unable to form battle lines, left completely vulnerable. But the Americans had no idea.
Around 2:00 a. m. on August 27th, the British reached Howard’s Tavern, just outside the Jamaica Pass. Soldiers dragged tavern keeper William Howard and his son from their beds at gunpoint.
Howe needed a guide. Howard refused. “We belong to the other side, General, and can’t serve you against our duty. ”
Howe’s response was calm and cold.
“You have no alternative. If you refuse, I shall shoot you through the head. ”
Howard guided them to the pass. Minutes later, the four American militia guarding the pass were captured without a shot, mistaking the approaching troops for fellow Americans.
Howe had maintained the element of surprise. He had flanked the entire American army. Back at Gowanus Pass, around 1:00 a. m.
, 4,000 British troops under General Grant launched a diversionary assault on Stirling’s Marylanders, holding them in place. Commanded on the ground by Major Gist, the Americans repulsed the British twice. At 6:00 a. m.
, Hessian artillery began pounding the center of the line, but the German troops didn’t advance—they just sat there, waiting. The Americans thought Grant’s attack was the main assault. Sullivan sent 400 men west to reinforce Stirling. The Americans thought they were winning.
Back in New York, Washington finally realized his mistake. This wasn’t a feint. He raced across the East River to Brooklyn Heights to take command. By 7:00 a.
m. , Cornwallis’s flanking column silently rounded the American position and crushed Colonel Miles’s small force, scattering them instantly. Then, at 9:00 a. m.
, the situation changed dramatically. Howe fired two heavy cannons—the signal for the Hessians to begin their frontal assault against Sullivan. Soon, the 10,000 British troops who had marched through Jamaica Pass appeared on the hilltops behind Sullivan’s position. Panic.
Sullivan’s men were hit from two directions at once—Hessians in front, British regulars from behind. The line shattered instantly. Officers screamed orders no one could hear. Men threw down their weapons and ran.
Others froze, unsure which way to go, and were shot where they stood. The Hessians, driven by rumors that Americans took no prisoners, bayoneted groups of surrendering soldiers. Sullivan and many of his troops were captured. Private Joseph Plumb Martin, who witnessed the carnage, would later write: “The demons of fear and disorder seemed to take full possession of all and everything that day.
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By noon, the American middle and left flank had been annihilated. Thousands of Continental soldiers—disorganized, terrified, separated from their officers—fled toward the only sanctuary left: the distant fortifications at Brooklyn Heights. But Cornwallis was faster. His elite regiments, the Black Watch of the 42nd Highlanders and his grenadiers, raced down Gowanus Road and seized the Old Stone House, the last escape route.
Thousands of American soldiers were trapped in what became known as the killing box. Behind them, Gowanus Creek, a tidal salt marsh where the mud could swallow a man to his chest. In front, Cornwallis and 2,000 veteran British soldiers blocking the only road to safety. On their flanks, 25,000 more enemy troops closing in.
Major Gist recounted: “Surrounded on all sides. ” The result was a bloodbath, as Hessians and British Highlanders methodically gave no quarter and no mercy. The American Revolution, just fifty-two days old, was dying on a Brooklyn battlefield. From his command post on Brooklyn Heights, Washington watched his army being destroyed.
He ordered the remaining Americans to retreat, but they were trapped. To reach safety, they would have to cross the deadly eighty-yard-wide barrier of the Gowanus Creek Marsh—a marsh no man was known to have ever crossed. If the British reached the creek first, the army would be slaughtered. Someone had to stand between them and the fleeing Americans.
Someone had to buy them time. Washington turned to the only organized troops still capable of fighting: the forces under Lord Stirling—the Marylanders and Delawareans. They received their orders: perform a rear-guard action, hold the line while their brothers escaped. They took their positions.
Musket smoke blanketed the land. The British pressed forward, appearing out of nowhere and everywhere through the smoke. With overwhelming numbers, the American detachments began to crumble. The Delaware lines were overrun, and Stirling soon ordered their retreat.
This left Stirling aware that nothing but a diversion of the enemy would save the entire detachment from destruction. Hurrying to the Maryland battalion, he gathered fewer than 400 men. Major Gist stood ready. Stirling gave them their mission: launch a suicidal counterattack on the British position at the Old Stone House, where Cornwallis’s troops were pouring murderous fire from its windows.
The order was to hold it at all costs—until every last American soldier had crossed the Gowanus Marsh to safety. In an act of bravery, Stirling remained behind to fight with Gist’s men. The 400 began their advance. Their muskets cracked in disciplined volleys, trying to slow the British surge, but the enemy kept coming.
British muskets erupted in almost solid sheets of lead. Cannons roared. Men fell, but the Marylanders closed ranks over their dead and dying comrades and pressed forward. The first assault was driven back, leaving brothers crumpled on the ground.
But something extraordinary happened. These bloodied men didn’t scatter or flee. They rallied. Impossibly, they reformed their lines amid the smoke and carnage.
They fired another ragged volley. Then, with fixed bayonets, they charged again, straight into a wall of fire. Again they were thrown back. Their ranks shattered.
The ground littered with their fallen. And then they did the unthinkable. They knew what another charge meant. They had seen it twice already.
They knew they were not going home. But across that marsh, their brothers were still escaping. A third time they rose. A third time they charged.
Few were left unbroken. Each step forward was a choice. They fired one last devastating volley at point-blank range, then crashed into the British lines. The battle erupted into brutal hand-to-hand combat.
Bayonets thrusting. Muskets swinging as clubs. Through smoke and fire, they pressed forward. Outnumbered ten to one, they embraced a truth as old as humanity: that there is no greater love than to lay down one’s life for another.
As the smoke settled, American muskets fell silent. The cost was staggering, but the line had held. For an astonishing hour, they stopped the entire British advance, buying priceless time for thousands of Washington’s men to reach safety. The mission was complete.
The price was paid. Washington, watching from Cobble Hill, famously cried out: “Good God, what brave fellows I must this day lose. ”
Stirling ordered the remaining troops to retreat across the swamp. Some men who tried to cross were bogged down and killed by British fire.
Others who could not swim were captured. Samuel Smith, a twenty-four-year-old captain, described the ordeal: “I took my company through a marsh until we were stopped by the dam of a mill. It was too deep for the men to ford. I and a sergeant swam over and got two slabs of wood into the water, on which we ferried over all who could not swim.
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Stirling, refusing to surrender his sword to Cornwallis, defiantly surrendered instead to a Hessian officer. The cost of the hour-long stand was devastating: 256 Marylanders killed and 100 captured in the combined assaults, wiping out over 60 percent of the attacking force—one of the largest fatality rates for any battle in American history. Fewer than twelve managed to return to Washington’s camp. Gist miraculously survived.
For those captured, many would perish from disease and starvation on English prison ships. By the late afternoon of August 27th, total American losses were over 1,000 dead and wounded, with another 1,000 captured. British losses were under 400 killed and wounded. The army had survived.
The Maryland 400 had broken the trap. But the British were not done. Sir Henry Clinton was ready to make a final assault on Brooklyn. Washington’s regrouped forces were pinned down, their backs to the river with nowhere left to run.
Then, on August 28th, something unexpected happened. The British stopped. Their army, poised to deliver the final blow, held its position. A terrible rainstorm swept across Brooklyn, turning the ground to mud.
But weather alone didn’t explain the pause. Howe was haunted by a memory: Bunker Hill. He remembered charging up that blood-soaked slope, the devastating volleys that cut down his men in rows. They had won that battle, but the cost had been terrible.
Now, facing another entrenched American position, they hesitated. They would wait. They would do this carefully. Washington seized the moment.
Late in the night, with campfires burning to deceive the enemy, the Continental Army began to move. Silently, desperately, they slipped toward the East River. Boats ferried them across to Manhattan. Oars muffled, voices hushed.
Every man knew that discovery meant annihilation. As dawn approached, Washington faced a catastrophe. Thousands of men remained on the Brooklyn shore, and daylight would expose them to British cannons and warships. They would be sitting ducks.
Then, just as the sun began to rise, an impenetrable fog rolled in from the river, blanketing the entire evacuation. It came at the precise moment needed, as if God himself had drawn a curtain across the scene. The fog held. The British saw nothing.
Boat after boat slipped across the water. Standing on the Brooklyn shore until the very end was Washington himself, refusing to leave until every one of his men had escaped. At 7:00 in the morning, he stepped onto the last boat. Nine thousand men were evacuated.
Not a single life was lost in the crossing. Later that morning, as the fog began to lift, the British woke to an astonishing sight: the American fortifications on Brooklyn were empty. The prize was gone. The war and Washington’s army would live to fight another day.
Washington’s escape would not have been possible without one desperate sacrifice. History calls them Washington’s Immortals—the Maryland 400, most barely out of boyhood with an average age of twenty-one, led by Lord Stirling and Major Mordecai Gist. Their repeated charges against overwhelming odds, their refusal to break even as they were cut down, had held back the British tide long enough for the Americans to reach safety. But the Maryland 400 didn’t just save an army.
They saved the revolution. Without their sacrifice, there would have been no evacuation, no fog-shrouded escape, no Continental Army to fight another day. The road to independence, to Yorktown, to victory runs directly through that killing field in Brooklyn where the Marylanders refused to yield. Washington never forgot their bravery.
He would later call the First Maryland Regiment his “Old Line”—troops he could depend on when all others broke. That tribute lives on today as Maryland’s official nickname: the Old Line State. Their legacy endures in another way. The 175th Infantry Regiment of the Maryland Army National Guard traces its lineage directly back to the First Maryland Regiment and the Maryland 400.
On their coat of arms is the bayonet, representing its first introduction to American arms at the Battle of Long Island. The swan’s head is from the coat of arms of the Gist family, commemorating Major Gist. The bodies of those young Marylanders were never properly buried. They fell where they fought, placed in shallow, unmarked graves scattered across farmlands that are now the streets of modern Brooklyn.
But their sacrifice endures. In Prospect Park today, a monument stands—not over their graves, but over their memory. A reminder of what they did on that desperate day. The Maryland 400 stood when retreat was the only rational choice.
They charged when surrender was inevitable. They gave everything so that a nation struggling to be born might survive. They fell in Brooklyn so that freedom would rise.