Battle of Long Island

On August 27, 1776, British and Hessian forces under General Sir William Howe defeated the Continental Army under George Washington in the largest battle of the Revolutionary War. The Battle of Long Island—also known as the Battle of Brooklyn or the Battle of Brooklyn Heights—resulted in the near-destruction of the American army and the loss of New York City. Only a skillful nighttime evacuation prevented a catastrophe that might have ended the war.

The British Expedition to New York

Following the British evacuation of Boston in March 1776, the ministry planned a massive expeditionary force to strike at New York, which British strategists regarded as the key to controlling the Hudson River corridor and dividing the rebellious colonies. Admiral Richard Howe and his brother, General William Howe, assembled the largest amphibious force Britain had ever deployed overseas: approximately 32,000 troops, including 8,000 Hessian soldiers, supported by a fleet of over 400 vessels, including 10 ships of the line and 20 frigates.

The armada began arriving in New York Harbor in late June 1776. The sight of hundreds of ships filling the harbor was, by contemporary accounts, the most impressive display of naval power the colonies had ever witnessed. A British officer wrote that the bay appeared “covered with a forest of masts.”

Washington, anticipating the British move, had marched his army from Boston to New York in April. The Continental Army, numbering approximately 19,000 men on paper but fewer in effective strength, was spread across Manhattan, Brooklyn, and the surrounding area. Washington’s defensive dispositions reflected the difficulty of defending a city surrounded by water against an enemy with naval superiority. He constructed fortifications on Brooklyn Heights, across the East River from Manhattan, and on Governor’s Island, but the sheer length of the coastline made comprehensive defense impossible.

The Landing at Gravesend Bay

On August 22, 1776, British forces began landing at Gravesend Bay on the southwestern shore of Long Island (present-day Brooklyn). Approximately 15,000 troops came ashore without opposition. The American forces on Long Island, numbering approximately 10,000 men under Major General Israel Putnam, were positioned along a ridge of hills known as the Heights of Guan, which ran roughly east-west across the island.

The Heights were defended by a series of passes. From west to east, these were the Gowanus Road (closest to the harbor), the Flatbush Road, the Bedford Road, and the Jamaica Pass—a narrow road that ran through the eastern end of the ridge. Washington had ordered the passes to be guarded but had not adequately fortified the Jamaica Pass, which was the most distant from the American positions and the most difficult to reinforce.

Howe’s Flanking Maneuver

General Howe’s plan, developed with the assistance of his intelligence officers and local Loyalist guides, exploited this vulnerability. The plan called for a three-pronged attack: Major General James Grant would demonstrate against the American right at the Gowanus Road with approximately 4,000 men; Hessian troops under Lieutenant General Leopold Philip von Heister would attack the center at the Flatbush Road with approximately 4,000 men; and Howe himself, with the main body of approximately 10,000 British regulars, would march through the Jamaica Pass to flank the American left and rear.

The flanking column began its march at approximately 9:00 p.m. on August 26, guided by local Loyalists who knew the terrain. The column marched through the night, covering approximately ten miles through the Jamaica Pass without encountering significant resistance. A small American patrol at the pass was captured before it could raise the alarm.

The Battle

At approximately 9:00 a.m. on August 27, the British flanking column emerged behind the American left flank. Simultaneously, Grant and von Heister launched their attacks on the American right and center. The American forces, commanded on the ground by Major General William Alexander (who styled himself Lord Stirling) and Major General John Sullivan, were caught in a devastating crossfire.

Stirling’s command on the American right fought stubbornly against Grant’s forces near the Gowanus Road. Stirling, commanding approximately 1,500 men including the 1st Maryland Regiment—Colonel William Smallwood’s unit, led in the field that day by Major Mordecai Gist because Smallwood was absent on court-martial duty in New York City—held a stone house and surrounding hills against repeated British attacks. The Maryland regiment, in particular, distinguished itself in a series of charges that allowed much of Stirling’s command to escape across the Gowanus Creek. Of approximately 400 Marylanders who engaged in these charges, roughly 256 were killed or captured—a casualty rate of nearly 65 percent. Washington, observing from Brooklyn Heights, reportedly exclaimed, “Good God, what brave fellows I must this day lose!”

Sullivan’s command in the center was overwhelmed by the combined pressure of the Hessian frontal attack and the British flanking maneuver. Sullivan himself was captured, and many of his troops were killed, captured, or scattered into the woods. The American forces that survived the initial engagement retreated to the fortifications on Brooklyn Heights.

The Retreat from Brooklyn Heights

By the afternoon of August 27, the remnants of the American army on Long Island—approximately 9,000 men—were concentrated in the fortifications on Brooklyn Heights, with the East River behind them. Howe, rather than assaulting the fortifications immediately, began siege operations, opening trenches and approaching the American lines methodically. This decision has been debated by historians: some argue that Howe was excessively cautious, squandering an opportunity to destroy the trapped American army; others contend that a frontal assault against fortified positions would have been costly and unnecessary, given that the Americans appeared to be trapped.

Washington crossed from Manhattan to Brooklyn Heights on the afternoon of August 27 and recognized the peril of his position. The American army was outnumbered, its morale was shaken, and its position was indefensible against siege operations. The East River, normally a barrier, became the means of escape.

On the night of August 29–30, Washington ordered a general evacuation of Brooklyn Heights. The operation was conducted with remarkable efficiency. Colonel John Glover’s Marblehead mariners—experienced boatmen from Massachusetts—organized a flotilla of boats that ferried the army across the East River to Manhattan. A thick fog that settled over the river around midnight concealed the movement from British observation. By dawn on August 30, approximately 9,000 troops, along with their artillery, supplies, and horses, had been evacuated without loss.

The evacuation was one of the most skillful operations of the war. Washington remained on the Brooklyn shore until the last boats departed, ensuring that the rearguard was safely embarked. The British, discovering the empty fortifications at dawn, were astonished that an entire army had disappeared across a tidal river in a single night.

Casualties and Consequences

American casualties at the Battle of Long Island were approximately 300 killed, 700 wounded, and 1,000 captured—a total of roughly 2,000. British and Hessian losses were approximately 60 killed, 260 wounded, and 20 missing—a total of roughly 340. The disparity reflected the nature of the engagement: the Americans had been outmaneuvered and subjected to concentrated attacks from multiple directions.

The loss of the battle led directly to the loss of New York City. Washington’s army, now on Manhattan, was in an equally precarious position. The British landed at Kip’s Bay on September 15, driving the Americans northward and entering New York City that same day. The city remained under British occupation for the duration of the war.

The loss of New York had significant strategic consequences. The city became the principal British base of operations in North America, serving as a staging area for subsequent campaigns and a haven for Loyalist refugees. The British occupation transformed New York into a crowded, disease-ridden city where thousands of American prisoners of war suffered in prison ships and makeshift jails.

Historical Assessments

The Battle of Long Island has been analyzed extensively by military historians. Washington’s defensive dispositions have been criticized for spreading his forces too thinly and for failing to adequately fortify the Jamaica Pass. His decision to place a significant portion of his army on Long Island, where it could be isolated by British naval power, has been questioned. Some historians argue that Washington should have concentrated his forces on Manhattan, where they could more easily retreat northward; others contend that the political pressure to defend Brooklyn was overwhelming and that Washington’s dispositions were reasonable given the intelligence available.

Howe’s conduct has also been the subject of debate. His flanking maneuver was well-conceived and well-executed, but his decision not to assault Brooklyn Heights immediately has been criticized as overly cautious. Some historians argue that Howe, who served simultaneously as a military commander and a peace commissioner, was reluctant to inflict a devastating defeat that might harden American resistance and undermine prospects for reconciliation. This interpretation—known as the “conciliation thesis”—remains controversial, with some scholars arguing that Howe’s caution reflected sound military judgment rather than political calculation. Howe’s defenders note that a frontal assault against fortified positions would have been costly and that the siege approach was the standard military practice of the era.

The battle also illustrated the limitations of the Continental Army at this early stage of the war. The army’s performance was uneven: some units, particularly the Maryland and Delaware regiments, fought with great courage and discipline, while others broke and fled under pressure. The lack of experienced officers, inadequate intelligence, and poor coordination between units all contributed to the defeat. These deficiencies would be addressed over the following years, particularly during the Valley Forge encampment of 1777–1778.

The battle’s legacy includes the enduring memory of the Maryland 400—the soldiers who sacrificed themselves to allow the army’s retreat. Their stand is commemorated in Maryland’s state history and is regarded as one of the most heroic episodes of the war. Major Mordecai Gist, who commanded the Maryland troops during their rearguard action, survived the battle and went on to serve with distinction in the southern campaign. The battle also reinforced Washington’s understanding that the Continental Army could not match the British in conventional engagements without significant improvements in training, discipline, and intelligence—a lesson that would shape his subsequent strategic decisions.

The loss of New York had lasting consequences for the civilian population. The city became a magnet for Loyalist refugees from across the colonies, swelling its population and creating a crowded, disease-ridden environment. Thousands of American prisoners of war were held in prison ships anchored in Wallabout Bay (present-day Brooklyn Navy Yard), where conditions were horrific. An estimated 11,000 prisoners died on these ships—more than the total number of American combat deaths in the entire war. The prison ships became a powerful symbol of British cruelty in American propaganda and memory.

The battle also had important implications for the conduct of the war in the years that followed. Washington’s experience at Long Island reinforced his preference for defensive operations and his reluctance to risk the army in pitched battles against superior forces. The Fabian strategy that Washington adopted in subsequent campaigns—avoiding decisive engagements while preserving the army and wearing down the enemy through attrition—was partly a product of the lessons learned at Long Island. The battle demonstrated that the Continental Army, in its current state, could not match British regulars in conventional combat, and that a different approach would be necessary to achieve ultimate victory.

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