The Maryland 400: The Desperate Last Stand That Saved George Washington’s Army at Brooklyn

On August 27, 1776, the American Revolution came terrifyingly close to collapse. Just weeks after declaring independence from Britain, George Washington’s Continental Army found itself trapped on Long Island, surrounded by a vastly superior British force. Thousands of soldiers faced capture or death, and the future of the fragile new nation hung in the balance. Yet in the middle of the disaster, fewer than 400 Maryland soldiers made a desperate stand that would become one of the most remarkable acts of sacrifice in the history of the American Revolution.

The Battle of Long Island was the first major battle fought after the Declaration of Independence, and it exposed the weaknesses of Washington’s inexperienced army. Against overwhelming odds, the Marylanders repeatedly attacked British positions near an old stone house, buying precious time for their fellow soldiers to retreat. Their losses were devastating, but their resistance helped preserve the Continental Army at a moment when its destruction could have ended the rebellion before it had truly begun.

The road to that desperate day had started more than a year earlier, when fighting erupted at Lexington and Concord in April 1775. British troops had attempted to seize colonial military supplies, but the operation ignited a wider conflict. Two months later, the Battle of Bunker Hill demonstrated that American forces could inflict enormous casualties on professional British soldiers, even when they ultimately lost the battlefield.

Washington subsequently led the Continental Army in a prolonged siege of Boston. In March 1776, British commander William Howe evacuated the city, giving the Americans their first significant strategic success under Washington’s leadership. However, the victory did not end the war. The British had merely withdrawn to regroup, and Washington understood that their next move could determine the fate of the rebellion.

He expected New York to become their next target. Its deepwater harbor could accommodate a powerful fleet, while control of the Hudson River would give the British a strategic route into the interior. If Britain could separate New England from the other colonies, the rebellion might be divided and defeated in pieces.

Washington moved his army into New York in April 1776 and began preparing defenses. The location, however, presented extraordinary challenges. Rivers, islands, and waterways made it difficult to coordinate troops, while the Americans had no navy capable of challenging British control of the surrounding waters. Loyalist sympathizers also remained active throughout the region, creating additional problems for an army already struggling with unreliable intelligence.

Washington made a critical decision that would soon prove costly. Believing the British would attack Manhattan directly, he divided his approximately 19,000 soldiers among several defensive positions. A smaller contingent was stationed on Long Island, where the terrain appeared to offer opportunities to slow an advancing enemy before it reached the principal American fortifications near Brooklyn Heights.

In early July, the British returned in overwhelming strength. Howe’s expedition eventually grew to more than 300 ships carrying tens of thousands of British regulars, Scottish Highlanders, and German troops hired to serve the Crown. The force represented one of the largest military expeditions Britain had assembled for an overseas campaign.

Meanwhile, the Declaration of Independence transformed the political stakes of the conflict. When the document was read to American troops in New York, celebrations broke out, and a crowd tore down a statue of King George III. Parts of the monument were reportedly melted down and recast into ammunition, turning a symbol of royal authority into material for the rebellion.

The celebrations could not conceal the Continental Army’s weaknesses. Many soldiers were inexperienced militia members with limited training, and desertion, disease, shortages, and disagreements between colonial units undermined military discipline. Washington commanded an army that remained far less professional than the force gathering across the harbor.

Among his most dependable soldiers, however, were the men of the First Maryland Regiment. Recruited largely from Maryland’s towns and surrounding communities, these young soldiers had developed a reputation for discipline and military readiness. Their uniforms distinguished them from many Continental troops, and their access to bayonets gave them an important advantage in close combat.

Their average age was approximately 21. Many were young farmers, merchants, clerks, and tradesmen who had left ordinary lives behind to fight for independence. Under Major Mordecai Gist, the Marylanders formed part of the American defensive line on Long Island, where they would soon face an enemy many times their number.

On August 22, British troops landed on Long Island. American intelligence underestimated the size of the force, and Washington initially suspected the landing might be a diversion intended to draw troops away from Manhattan. He sent reinforcements across the East River, but the Americans still faced a serious numerical disadvantage.

The principal American defenses occupied a series of hills known as the Guan Heights. Three major passes were guarded by Continental troops, but a fourth route, Jamaica Pass, remained dangerously exposed. A Loyalist informant revealed the route to British commanders, who recognized an opportunity to outflank the American position.

On the night of August 26, British troops under Sir Henry Clinton began a long march through the darkness. Leaving their campfires burning to conceal their movement, thousands of soldiers advanced toward Jamaica Pass. At approximately two in the morning, they reached a tavern outside the pass and forced its reluctant keeper to guide them forward.

The small American patrol guarding the route was captured without firing a shot. By dawn, the British had moved around the American flank, placing a substantial force behind the Continental defenses. At the same time, another British column attacked the American position near Gowanus Pass, keeping Lord Stirling’s troops occupied while the encirclement developed.

For a time, the Americans misunderstood the situation. British attacks against the forward positions appeared to be the main assault, and reinforcements were sent toward the fighting. But as the morning progressed, the consequences of Washington’s intelligence failure became unmistakable.

British troops emerged behind the American lines, while German forces advanced from the front. The Continental Army was struck from two directions, and its defensive positions began to disintegrate. Soldiers struggled to identify safe routes, officers lost control of their men, and entire groups were captured or scattered across the battlefield.

Major General John Sullivan’s position collapsed, while other American units suffered heavy losses. Thousands of frightened soldiers attempted to retreat toward the fortifications at Brooklyn Heights, their only remaining refuge. British forces pressed forward, threatening to cut off the escape routes before the Americans could reach safety.

Near Gowanus Road, British troops occupied an old stone house that controlled a crucial route toward the American lines. Beyond it lay Gowanus Creek and its surrounding marshland, a difficult obstacle for men attempting to flee under fire. With British troops closing in, the Americans faced the possibility of being trapped against the water and destroyed.

Washington needed time to save the surviving army. The troops under Lord Stirling, including the Marylanders and men of the Delaware Regiment, were among the few organized forces still capable of mounting a coordinated resistance. Their task was to hold the British back while the rest of the Continental soldiers withdrew.

As the American position deteriorated, Stirling gathered a small force of Maryland soldiers under Major Gist and ordered them to attack the British position near the stone house. The mission was extraordinarily dangerous. They were being sent against experienced troops occupying a strong defensive position, with little prospect of escaping without heavy casualties.

The Marylanders advanced under intense fire. Their muskets answered the British volleys, but the defenders possessed superior numbers and a formidable position. The Americans were driven back, leaving dead and wounded men on the ground. Yet the surviving soldiers regrouped and attacked again.

The second assault also failed to dislodge the British. Still, the Marylanders refused to abandon their task. They reorganized once more and launched another charge, pressing toward the enemy position despite the terrible cost of the previous attacks. Their resistance forced the British to continue fighting rather than immediately pursuing the retreating Americans.

The fighting became desperate and close. Musket fire filled the air, and soldiers struggled through smoke as the opposing forces clashed around the stone house. The Marylanders could not defeat the much larger British force, but they did not need to win the battlefield. Their objective was to delay the enemy long enough for their comrades to escape.

That delay came at an extraordinary price. The regiment suffered catastrophic losses, with hundreds killed, wounded, or captured during the fighting. Only a small number of the men involved in the repeated attacks returned to Washington’s lines. Major Gist survived, but the unit that had entered the battle as one of the Continental Army’s most promising formations was nearly destroyed.

The wider American defeat was severe. Hundreds of soldiers were killed or wounded, and many more were captured. British losses were considerably lower, and the Crown’s forces appeared to have achieved the decisive victory they needed. Yet the Continental Army had not been annihilated, and that distinction would prove crucial.

The British advance paused as Washington’s surviving troops withdrew toward Brooklyn Heights. A combination of difficult weather, the need to prepare for another assault, and British caution following the bloody experience at Bunker Hill gave the Americans a narrow opportunity to escape. Howe had the advantage, but Washington still had a way to preserve his army.

During the night of August 29–30, the Americans began a carefully organized evacuation across the East River to Manhattan. Soldiers moved toward the waterfront while boats ferried men, equipment, and supplies away from the threatened position. The operation depended on secrecy, favorable conditions, and the ability to move thousands of men before the British realized what was happening.

A thick fog settled over the river as the evacuation continued, obscuring the American movement from British observation. The conditions helped conceal the retreat until the last boats could carry the remaining soldiers across. By the morning of August 30, Washington had successfully withdrawn approximately 9,000 men from Brooklyn without losing a soldier during the crossing.

The escape did not erase the defeat at Long Island, nor did it guarantee American independence. Washington’s army would endure further retreats, shortages, and devastating setbacks. But it survived to continue the war, denying Britain the opportunity to end the rebellion in its earliest months.

The Maryland soldiers who fought near the stone house became remembered as the Maryland 400, a name associated with extraordinary courage and sacrifice. Their story represents a crucial moment when a small group of soldiers accepted almost certain destruction to give thousands of their comrades a chance to survive.

Their legacy also became part of Maryland’s military identity. Washington’s later association of Maryland troops with dependable service helped inspire the state’s nickname, the “Old Line State.” The Maryland Army National Guard’s 175th Infantry Regiment traces its lineage to the state’s early infantry tradition, preserving a connection to the soldiers who fought in the Revolution.

Today, a monument in Brooklyn’s Prospect Park commemorates the Marylanders’ sacrifice. The precise details of the battle have been retold and dramatized over generations, but the essential truth remains: American soldiers fought desperately during a disastrous defeat, and the resistance of Maryland troops helped protect the retreat of Washington’s army.

The Revolution did not survive because the Americans won the Battle of Long Island. They lost it decisively. It survived because their army escaped, regrouped, and continued fighting when the cause appeared close to collapse. The Maryland 400 became a lasting symbol of the determination that made that survival possible.

Their stand was not the end of the war, but it helped ensure there would be a war to fight. On a battlefield outside Brooklyn, young soldiers gave their lives so that the struggle for American independence could continue. Their sacrifice remains a powerful reminder that, at pivotal moments in history, the survival of a larger cause can depend on the courage of a few.