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Battle of Long Island


The Battle of Long Island, also known as the Battle of Brooklyn, was the first major battle of the Revolutionary War since the Continental Congress formally adopted the Declaration of Independence on July 4, 1776. Although American independence had been declared, it still remained to be secured on the battlefield. As the war moved to New York, General George Washington and his amateur army were confronted by the largest expeditionary force of the eighteenth century. On August 27, British and Hessian forces under General William Howe attacked American forces stationed on the western end of Long Island, in present-day Brooklyn, and skillfully defeated Washington’s army. While Washington had been totally outmaneuvered and outgeneraled by Howe, the American commander coordinated a skillful retreat on the foggy night of August 29, saving his army from destruction. General Howe could have ended the war at the Battle of Long Island, but the Americans lived to fight another day. More dark moments would follow, but over time, General Washington would learn from his mistakes and stun the world’s premier war machine of its day.

In March 1776, the British evacuated Boston and General Washington correctly anticipated that the enemy’s next target would be New York. Washington knew that holding New York might not be possible militarily, but politically, it had to be attempted. By mid-April, he had marched his army to Lower Manhattan. Washington had around 19,000 troops on hand, nearly half of which were militia, poorly armed, equipped, trained, and in certain cases led. His remaining troops, the regulars, or Continentals, were better prepared in those categories, but were still largely untried. With such extensive territory to cover, Washington and his amateur army got to work preparing for the British. General Washington strengthened the batteries that guarded the harbor and constructed forts in northern Manhattan and across the East River on Long Island. As he waited throughout June for the British to appear, the American commander hoped that somehow his undisciplined troops could hold off an attack, which he confidently felt would come in Manhattan. The British were indeed coming and they would make their presence felt once they arrived.

General George Washington. (Photo: Wikimedia Commons)

The British began to arrive in late June and over the summer more elements continued to appear, assembling on Staten Island and in the harbor. To put an end to the rebellion, the Crown had sent the largest expeditionary force of the eighteenth century: nearly 400 ships and 32,000 regular troops. British General William Howe had a more numerous force than the entire population of New York or even Philadelphia, which was the largest city in America with a population of about 30,000. Howe had a remarkable force at his disposal, leading one man to remark that it looked like “all London afloat.” In his attempts at negotiation, General Howe offered a pardon to the rebels. Washington’s reply echoed the sentiments held by many Patriots: “Those who have committed no fault want no pardon.” The time to fight was near.

General William Howe. (Photo: Wikimedia Commons)

American General Nathanael Greene was seriously ill on the eve of the Battle of Long Island. At age thirty-three, Greene was the youngest general officer in the American army. Despite his youth, he had made a great impression on Washington and the commander-in-chief counted on him more than anyone. Since Greene was “sick nearly to death,” he was relieved of command and moved from Brooklyn Heights across the river to a house several miles above New York. For a man who had never commanded a large army in the field, Washington would soon have to deal with the greatest challenge of his military career. When that time came, he would not have his trusted young subordinate by his side.

General Nathanael Greene. (Photo: Wikimedia Commons)

On August 22, Crown forces began moving to Gravesend Bay on Long Island, in what is now southwest Brooklyn. Anticipating a possible landing there, Washington posted more than a third of his force on Brooklyn Heights under the command of General Israel Putnam. General John Sullivan was stationed to the south and General William Alexander, who called himself Lord Stirling, to the southwest on the Heights of Guan. Guards were posted along the main roads leading through the heights, but the Americans failed to properly secure the rarely used Jamaica Pass to the east. This proved to be a fatal mistake for General Washington and his army.

On the evening of August 26, Sir Henry Clinton, Lord Charles Cornwallis, and Sir Hugh Percy, with 10,000 men under General Howe’s personal command, quietly marched through Jamaica Pass and were prepared to attack the Americans from the rear. Historian David McCullough argues, “Had there been American cavalry to serve as “eyes and ears,” or had there been reliable intelligence, the defenders might have had a better chance.” Unfortunately for the Continental Army, there was neither, and in the morning, there would be hell to pay.

On the morning of August 27, the American front line was attacked from front and behind. “It is impossible for me to describe the confusion and horror of the scene that ensued,” an American veteran wrote years later: “the artillery flying with chains over the horses’ backs, our men running in almost every direction, and run which way they would, they were almost sure to meet the British or Hessians.” The raw and undisciplined American troops were hit hard. Forced to retreat, many Patriots desperately crossed a swamp at Gowanus Creek, now the Gowanus Canal. “Some of them were mired and crying to their fellows for God’s sake to help them out; but every man was intent on his own safety and no assistance was rendered.”

The Battle of Long Island by Alonzo Chappel. (Photo: Wikimedia Commons)

General Washington had hurried across the East River from Manhattan at about 9:00 a.m., or just as Howe’s signal guns sounded. David McCullough notes, “Accounts of Washington’s activities as the battle raged are few and somewhat conflicting.” Washington most likely observed the struggle from a vantage point on Brooklyn Heights. Although his army was met with disaster, there were examples of tremendous courage and fighting spirit.

General Sullivan’s men fought bravely, but were cut down by Hessian artillery and bayonets. When the general realized that the main British force had come through the Jamaica Pass, he knew that he would soon be surrounded. Sullivan ordered his men to retreat to Brooklyn Heights before he was captured.

General John Sullivan. (Photo: Wikimedia Commons)

Lord Stirling led one of the most remarkable resistances in American military history. Leading 400 Marylanders in a desperate fight against the Redcoats, Stirling and his men fought savagely to cover the American retreat. Stirling and the “Maryland 400” launched repeated attacks against the British, who had established their line on the Gowanus Road beside a stone farmhouse. The fighting here “was the most savage of the day,” according to McCullough. As General Washington watched the Marylanders attack and get cut down time after time, he is said to have cried out, “Good God, what brave fellows I must this day lose!” More than 250 Marylanders were killed and Lord Stirling was taken prisoner. Until that morning, the Marylanders had never faced an enemy, but without any doubt; they unforgettably proved their mettle, fighting like wolves and allowing many comrades to escape.

Lord Stirling at the Battle of Long Island. (Photo:

By the early afternoon, General Howe halted the fighting. The American rout had been so complete and the British advance so rapid that many of Howe’s officers were eager to keep going and carry the attack straight to the American works. Washington’s army was in disarray and had the British continued the attack, the war might very well have ended then and there, but that is easy to say with hindsight. At the Battle of Bunker Hill in June 1775, General Howe had seen how costly it could be to confront entrenched Americans frontally. His troops had also been up and marching all night, not to mention fighting a battle that had already lasted for several hours. With momentum on his side, Howe decided to entrench around the American position and lay siege. General Washington however, was not going to wait around for that to happen.

Before the Americans could be surrounded, Washington ordered his men to evacuate Long Island. From late in the evening on August 29 to dawn on the following morning, the American commander-in-chief watched as 9,000 of his troops were rowed back to Manhattan. The escape could have easily failed. As the darkness faded and morning light approached, a large part of the army was still waiting to embark. A miracle was needed, and providence offered a helping hand. According to McCullough, “Just at daybreak a heavy fog settled in over the whole of Brooklyn, concealing everything no less than had the night.” The fog was so thick that one “could scarcely discern a man at six yards distance,” remembered a soldier. Not a life was lost during the operation and according to eyewitnesses, General Washington was the last man to leave Brooklyn.

Retreat at Long Island, depicting General Washington directing the American retreat back to Manhattan. (Photo:

In its first great test under fire, the American army had nearly been destroyed, but it would live to fight again. Many more moments of unimaginable difficulty would follow, but in time, George Washington would have his day.

Counting both armies and the Royal Navy, more than 40,000 men had taken part in the Battle of Long Island. It was by far the largest battle ever fought in North America up to that time. The battlefield ranged over six miles, and the fighting lasted just over six hours. Americans losses were around 300 killed, 800 wounded, and over 1,000 taken prisoner, including three generals, Sullivan, Stirling, and Nathaniel Woodhull. It is estimated that the British lost some 64 killed, 293 wounded, and 31 missing or captured.


1776 By David McCullough.

American Battlefield Trust: Battle of Brooklyn.

George Washington's Mount Vernon: Battle of Long Island.

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