How the Maryland 400 Saved Washington's Army _ Battle of Long Island 1776

August 27th, 1776. The Battle of Long Island. The first major battle of the Revolutionary War. And for the Americans, a catastrophe. A British surprise attack sends George Washington's army into chaos. Thousands of American soldiers are now trapped, encircled by 20,000 enemy troops. Independence, declared just five weeks ago, is about to be crushed. Then, fewer than 400 men from the 1st Maryland Regiment, young farmers and merchants, volunteer for a suicide mission. Hold the line. Buy time for the army to escape. The final hour is a terrifying last stand. This is the story of how the Maryland 400 saved Washington's army, and the American Revolution itself. April 19th, 1775. Lexington and Concord. The first shots of the American Revolution. What began as a raid on colonial weapons, quickly spiraled into open warfare. Two months later came the carnage of Bunker Hill. The British won, but paid a devastating price. Over a thousand casualties, their costliest engagement of the entire war. The colonists had proved they could stand and fight against the world's most powerful army. For nearly a year, General George Washington laid siege to Boston. Finally, in March of 1776, British Commander General William Howe is forced to evacuate, sailing north to Nova Scotia to regroup. Washington had won his first major victory, but he knew this was far from over. The British would return. The question was, where? Washington predicted that the next target would be New York. The city's deep water ports could supply and anchor the entire British fleet. Control New York, and you control 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 were 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 were actively working against Washington, intercepting vital messages and capturing supplies. Spies were everywhere. Trust was scarce. Washington assumed they'd strike Manhattan directly. But he makes a critical mistake. He divides his army. 19,000 men, scattered across multiple positions. The bulk stay on Manhattan to defend the city. A smaller force, just 4,500 men, are sent across the East River to Long Island. In early July, 1776, General Howe returned. A massive British armada, growing to over 300 ships, arrives off Staten Island. The largest expeditionary force ever assembled by the British Empire. Packed aboard are more than 32,000 soldiers, British regulars, Scottish highlanders and thousands of German Hessian mercenaries. Leading them are 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 signs the Declaration of Independence. When news of independence reaches New York, Washington gathers 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 and tore down the massive equestrian statue of King George III. Cutting off the king's head, they mount it on a spike outside a local tavern. The rest of the statue is then melted down and cast into musket balls. The tyrant king transformed into bullets for his own army. But across the harbour on Staten Island, the celebration looked very different. 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'd 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 still, 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 1st Maryland Regiment is different. While most Continental soldiers drilled poorly and fought in rags, the Marylanders were well-paid, well-trained and looked like professionals. Crisp uniforms, blue coats and 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 21 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, seeing the hunting shirts meant one thing, American sharpshooters. 700 strong, the Maryland Regiment was commanded by Colonel William Smallwood, but Smallwood would be unexpectedly called away to oversee a court-martial, with command falling to General William Alexander, who styled himself Lord Sterling after a disputed Scottish title. Major Mordecai Gist, a Baltimore native, leads the regiment. 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. 4,000 British troops, led by Sir Henry Clinton and Lord Cornwallis, land unopposed on Long Island. Within hours, 15,000 troops are ashore, alongside 40 pieces of artillery. Hundreds of loyalists swarm the beach to greet them as liberators. Word reaches Washington in New York, but the report is wrong. His scouts estimate only 8,000 troops had landed. Washington is convinced this is a feint. The real attack would come at Manhattan. So he sends a meager 1,500 reinforcements to Brooklyn, totalling the American forces on Long Island to 6,000 men. The American defence is centred across the Gwan Heights, a 150-foot ridge of hills, blocking the direct route to fortifications at Brooklyn. Three main passes through the heights, Gowanus, Flatbush and Bedford, are heavily guarded. By stationing men on the higher ground, heavy casualties could be inflicted on the British before the troops would fall back to the main defences. General Israel Putnam commands Brooklyn Heights. Lord Stirling and his Marylanders and the 1st Delaware Regiment hold the American right at Gowanus Pass, with 1,600 men. And Major General John Sullivan, commander of the force on Long Island, holds the centre with 1,500 men. Colonel Samuel Miles and his Pennsylvania Rifle Regiment holding the hill to the east at around 500 men. But there is a fourth route, the Jamaica Pass, far to the east. A local loyalist informs General Clinton of the route, patrolled by just four militia officers on horseback. Clinton sees the opportunity. General Howe approves. On August 26th, at 9pm, under cover of darkness, 10,000 British troops begin a night march toward the Jamaica Pass. It is one of the most audacious gambles of the war. The column stretches over two miles. An advance party is led by Clinton, followed by Cornwallis and General Howe. They leave 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 them vulnerable. But the Americans had no idea. Around 2am on August 27th, they reach Howard's Tavern, just outside the Jamaica Pass. British soldiers drag tavern keeper William Howard and his son from their beds at gunpoint. General Howe needed a guide. William 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 guides them to the pass. Minutes later, the four American militia guarding the pass are captured without a shot, mistaking the approaching troops as fellow Americans. General Howe has maintained the element of surprise. He has flanked the entire American army. Back on the east part of Long Island, at around 1am, 4,000 British troops under General Grant launch a diversionary assault on Stirling's Marylanders at Gowanus Pass, holding them in place. Commanded on the ground by Major Mordecai Gist, twice the British attack the hill and twice they are repulsed. At 6am, in the center, Hessian artillery begin pounding the heights, but the German troops don't advance. They just sit there, waiting. The Americans think Grant's attack is the main assault. General Sullivan sends 400 men west to reinforce Stirling. The Americans think they are winning. Back in New York, Washington finally realizes his mistake. This wasn't a feint. He races across the East River to Brooklyn Heights to take command. By 7am, Cornwallis' flanking column silently rounds the American position and crushes Colonel Miles' small force, scattering them instantly. Then, at 9am, the situation dramatically changes. General Howe fires two heavy cannons, the signal for the Hessian troops to begin their frontal assault against Sullivan. Soon, the 10,000 British troops who'd marched through Jamaica Pass appear on the hilltops behind Sullivan's position. Panic. Sullivan's men are hit from two directions at once. Hessians in front, British regulars from behind. The line shatters instantly. Officers scream orders that no one could hear. Men throw down their weapons and run. Others froze, unsure which way to go, and are shot where they stood. The Hessians, driven by rumors that Americans take no prisoners, bayonet groups of surrendering soldiers. Major General Sullivan and many of his troops are captured. Private Joseph Plum 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. 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 race down Gowanus Road and seize the old stone house, the last escape route. Thousands of American soldiers are trapped in what is 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 are closing in. Major Gist recounts, Surrounded on all sides, the result was a bloodbath as the Hessians and British Highlanders methodically gave no quarter or mercy. The American Revolution, just 52 days old, is dying on a Brooklyn battlefield. From his command post in Brooklyn Heights, General George Washington watches through his spyglass as his army, the only army America had, is being destroyed. He orders the remaining Americans to retreat, but they are trapped. To reach safety, they would have to cross the deadly, 80-yard-wide barrier of the Gowanus Creek Marsh, a marsh that no man has been known to ever cross. 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 Sterling, the Marylanders and Delawareans. They receive their orders, perform a rearguard action, hold the line while their brothers escape. They take their positions, musket smoke blanketing the land. The British press forward, appearing out of nowhere and everywhere through the smoke. With overwhelming numbers, the American detachments begin to crumble. The Delaware lines are overrun. Sterling soon orders their retreat as well. This left Lord Sterling aware that nothing but a diversion of the enemy would save the entire detachment from destruction. Hurrying to the Maryland battalion, he gathers fewer than 400 men. Major Mordecai Gist stands ready. Sterling gave them their mission. Launch a suicidal counter-attack on the British position at the Old Stone House, where Cornwallis' troops were pouring murderous fire from its windows. The order, hold it at all costs, hold it until every last American soldier has crossed the Kiwanis Marsh to safety. In an act of bravery, Sterling remains behind to fight with Gist's men. The 400 begin their advance. Their muskets crack in disciplined volleys, trying to slow the British surge. But the enemy keeps coming. British muskets erupt in almost solid sheets of lead. Cannons roar. Men fall. But the Marylanders close ranks over their dead and dying comrades and press forward. The first assault is driven back, leaving brothers crumpled on the ground. But something extraordinary happens. These bloodied men don't scatter or flee. They rally. Impossibly, they reform their lines amid the smoke and carnage. They fire another ragged volley, then with fixed bayonets charge again, straight into a wall of fire. Again they are thrown back, their ranks shattered, the ground littered with their fallen. And then they do the unthinkable. They know what another charge means. They had seen it twice already. They know they are not going home. But across that marsh, their brothers are still escaping. A third time, they rise. A third time, they charge. Fewer now, but unbroken. Each step forward a choice. They fire one last devastating volley at point-blank range, then crash into the British lines. The battle erupts into brutal hand-to-hand combat, bayonets thrusting, muskets swinging as clubs. Through smoke and fire, they press forward, not in blind rage, but with love. Outnumbered ten to one, they embrace a truth as old as humanity, that there is no greater love than to lay down one's life for another. As the smoke settles, American muskets fall silent. The cost is staggering, but the line has held. For an astonishing hour, they stop the entire British advance, buying priceless time for thousands of Washington's men to reach safety. The mission is complete. The price is paid. Washington, watching from Cobble Hill, famously cries out, Good God, what brave fellows I must this day lose. Lord Stirling orders the remaining troops to retreat across the swamp. Some of the men who tried to cross are bogged down, only to be killed by British fire. Others who could not swim are captured. Samuel Smith, a 24-year-old captain, describes 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. Lord Stirling, refusing to surrender his sword to Cornwallis, defiantly surrenders to a Hessian officer. The cost of the hour-long stand was devastating. 256 Marylanders are killed and 100 captured in the combined assaults, wiping out over 60% of the attacking force, one of the largest fatality rates for any battle in American history. Fewer than 12 manage to return back to Washington's camp. Fortunately for Gist, he miraculously survives. For those captured, many will perish from disease and starvation on English prison ships. By the late afternoon of August 27th, the total American losses are over 1,000 dead and wounded and another 1,000 captured, with British losses under 400 killed and wounded. The army is surviving. The Maryland 400 had broken the trap. But the British are not done. Sir Henry Clinton is ready to make a final assault on Brooklyn. Washington's regrouped forces are pinned down, their backs to the river, with nowhere left to run. The next day, on August 28th, something unexpected happens. The British stop. Their army, poised to deliver the final blow that would crush Washington's forces, hold its position. A terrible rainstorm sweeps across Brooklyn, turning the ground to mud. But weather alone didn't explain the pause. The British commander, William Howe, was haunted by a memory. Bunker Hill. He remembered charging up that blood-soaked slope, the devastating volleys that cut down their men in rows. They had won that battle, but the cost had been terrible. Now, facing another entrenched American position, they hesitate. They would wait. They would do this carefully. Washington seizes the moment. Late in the night, with campfires burning to deceive the enemy, the Continental Army begins to move. Silently, desperately, they slip toward the East River. Boats ferry them across to Manhattan, oars muffled, voices hushed. Every man knows that discovery means annihilation. As dawn approaches, Washington faces a catastrophe. Thousands of men remain on the Brooklyn shore, and daylight would expose them to British cannons and warships. They would be sitting ducks, helpless targets in the morning light. Then, on August 30th, just as the sun begins to rise, an impenetrable fog rolls in from the river, blanketing the entire evacuation. It comes at the precise moment needed, as if God himself has drawn a curtain across the scene. The fog holds. The British see nothing. Boat after boat slips across the water, and there, standing on the Brooklyn shore until the very end, is Washington himself, refusing to leave until every one of his men has escaped. At 7 in the morning, Washington steps onto the last boat. 9,000 men are evacuated. Not a single life is lost in the crossing. The Continental Army survives. The Revolution survives. It was nothing short of miraculous. Later that morning, as the fog began to lift, the British woke to an astonishing sight. The American fortifications on Brooklyn are 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 21. Led by Lord Sterling 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. George Washington never forgot their bravery. He would later call the 1st 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 also endures in another way. The 175th Infantry Regiment of the Maryland Army National Guard traces its lineage directly back to the 1st Maryland Regiment and the Maryland 400. On their coat of arms is the bayonet, representing its first introduction to American arms in the Battle of Long Island. The swan 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. Who 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. If you enjoyed this journey through history, subscribe to Clear and Present History for more documentaries and untold stories from the past. A like or comment helps keep these stories from being forgotten. And if you believe the lessons of history still matter, becoming a supporting member helps us go deeper, funding the research and production that allow us to explore overlooked stories and preserve the hard-won wisdom of the past. From all of us at Clear and Present History and myself, Steve Kristoff, thank you. Until next time.