Less than two months after Congress declared the thirteen colonies independent, George Washington faced the task of defending one of America's most important cities against a British force of unprecedented scale.
The result was the Battle of Long Island, fought principally on August 27, 1776. It was the first major battle after the Declaration of Independence and the largest engagement of the Revolutionary War. For the Continental Army, it was also a severe defeat, with the army surviving by a remarkably narrow margin.
Long Island or Brooklyn?
The battle appears under two names: the Battle of Long Island and the Battle of Brooklyn. Both refer to the same engagement.
In 1776, Brooklyn was a collection of settlements on the western end of Long Island, separated from the city of New York on Manhattan by the East River. It was not yet one of New York City’s five boroughs. Contemporary maps and later accounts therefore described the fighting broadly as taking place on Long Island.
Much of the action, however, occurred within what is now Brooklyn, from the wooded heights near present-day Prospect Park and Green-Wood Cemetery to Gowanus and the American fortifications at Brooklyn Heights. For the readers of today, Battle of Brooklyn often describes the geography more recognizably.
Why New York?
New York offered the British several advantages at once. Its deep harbor could accommodate the Royal Navy, and the waterways surrounding Manhattan allowed British ships to move men and supplies with considerable freedom. Control of the Hudson River corridor also opened a route north toward Canada and raised the possibility of separating New England from the other colonies.
Washington understood the danger and began shifting troops to New York while defenses were built across Manhattan and Long Island.
General William Howe began arriving at Staten Island in early July, followed by thousands of British and Hessian troops and an enormous naval presence under his brother, Admiral Richard Howe. By late summer, more than 30,000 British and allied soldiers were available for the New York campaign.
Washington commanded a smaller army, and many of his men had limited battlefield experience. He also had no certainty about where Howe intended to strike. Manhattan, Long Island, and positions farther north all had to be considered, forcing Washington to spread his forces across several possible targets.
That uncertainty would shape what happened next.
The British Land on Long Island
On August 22, British transports carried an initial force of roughly 10,000 troops across the Narrows from Staten Island and landed them near Gravesend Bay on Long Island. Washington still suspected that the landing might be a diversion before a larger attack on Manhattan. He reinforced Long Island but did not concentrate his entire army there.
The American defenses had two principal layers.
Closer to Brooklyn Heights stood a fortified line protecting the approaches to the East River. Farther south, American troops occupied the wooded ridge known as the Heights of Guan, a chain of hills crossing the roads that led north from the British position toward Brooklyn.
Several passes through those heights had to be defended… and that was the problem. The Americans watched important routes near Flatbush and Bedford, but the road through Jamaica Pass, farther to the east, was barely protected. Local Loyalists made certain the British knew it.
August 26: Howe Makes His Move
The first shots associated with the battle had already produced one of its stranger footnotes. On August 26, two British soldiers reportedly wandered into a watermelon patch, where American pickets fired upon them.
After dark, Howe put his larger strategy into motion. He had devised a plan to fix American attention on their front while sending a large force around their exposed left. British and Hessian troops would threaten the American positions elsewhere, while the main flanking column moved toward Jamaica Pass.
Thousands of troops marched through the night. The maneuver depended upon reaching the pass without alerting the Americans. British troops, including forces under Henry Clinton and Charles Cornwallis, approached before dawn and found the route only lightly defended. The weakness in Washington's line was now a road into his rear.
August 27: Attacked from Both Directions
Fighting spread across the American position early the next morning.
Near the center, Hessian troops pressed Americans around the wooded heights and the Flatbush road. To the west, British troops under General James Grant engaged American forces nearer the Gowanus road. Those attacks kept American attention focused on the forces directly in front of them.
Then Howe’s flanking column arrived from behind.
American units that had been fighting toward the south suddenly faced British regulars advancing into their rear. Formations broke apart, retreat routes narrowed, and troops were forced to fight their way back through woods, fields, and roads already crowded with men trying to reach Brooklyn Heights. Some soldiers escaped while others were surrounded or captured.
Washington crossed from Manhattan as the fighting intensified and watched the situation deteriorate from the Brooklyn lines. By then, Howe’s maneuver had already decided the battle.
The Marylanders at Gowanus
One of the best remembered episodes of the battle occurred during the American retreat.
Near Gowanus, Lord Stirling ordered most of his troops toward the difficult crossing at Gowanus Creek while roughly 400 Maryland and Delaware soldiers remained behind as a rear guard. Facing a much larger British and Hessian force, they launched repeated attacks near the Old Stone House, buying time for other Americans to reach Brooklyn Heights.
The cost was severe. The National Park Service estimates that 256 Maryland and Delaware soldiers were killed near the Old Stone House, while more than 100 were captured. The rear guard became known collectively as the Maryland 400, although both the composition of the force and the exact number engaged were more complicated than the name suggests. Washington is traditionally said to have watched their stand and lamented the loss of such men as the battle continued below.
Elsewhere, retreating troops struggled across the marshes and waters around Gowanus Creek. Some drowned, some were captured, and others managed to reach the American fortifications at Brooklyn Heights.
By the end of the day, the British controlled the field.
Trapped at Brooklyn Heights
The defeat left Washington with a more serious problem than the loss of ground. Roughly 9,000 American troops were concentrated behind the defenses at Brooklyn Heights with the East River at their backs. British forces stood in front of them, while British warships threatened their remaining route across the river.
If Howe launched another major assault, a large portion of the Continental Army could be destroyed or captured. He chose not to.
The British commander had seen what determined Americans behind fortifications could do at Bunker Hill the previous year, when British troops ultimately took the ground but suffered enormous casualties. At Brooklyn, he chose instead to entrench and prepare for a siege.
That decision gave Washington the time he needed to strategize an escape.
An Army Disappears
By August 29, remaining at Brooklyn Heights had become increasingly dangerous. Rain had soaked the army, British siege preparations were advancing, and warships threatened to move into the East River and close the remaining route to Manhattan.
The American council of war agreed to withdraw. The problem was getting thousands of men, along with artillery, horses, wagons, and supplies, across the East River without alerting the British nearby.
Colonel John Glover’s Massachusetts regiment provided a key advantage. Many of his men were experienced mariners from Marblehead, Massachusetts, and knew how to handle boats in difficult conditions, described by Washington as men “bred to the sea.”
Through the night of August 29 and into the morning of August 30, Glover’s men ferried the army across the river under strict secrecy. Soldiers were ordered to keep silent, wagon wheels were muffled, and campfires remained burning so the American position would still appear occupied from the British lines.
Weather helped conceal the final stages. A dense fog settled over Brooklyn toward morning, while conditions on the Manhattan side remained clearer, allowing the last boats to continue crossing without revealing the extent of the retreat.
Washington remained until the operation was nearly finished. When British troops finally approached the American works, the defenses were empty. The Continental Army had escaped.
Defeat Without Destruction
The Battle of Long Island was not an American victory. British and Hessian forces had outmaneuvered the Continental Army and inflicted far greater losses. Estimates vary, but American killed, wounded, missing, and captured numbered well over 1,000 and may have approached 2,000. British losses were considerably smaller.
The defeat also opened the way for Britain to take New York City. British forces entered Manhattan in September, and New York remained under British occupation until 1783.
However, Howe had not accomplished the destruction of Washington’s army. The Continental Army could surrender territory and continue the war. Losing the army itself would have threatened the Revolution in a far more fundamental way. Washington's evacuation from Brooklyn did not erase his mistakes or reverse the British victory, but it preserved the force upon which the American cause still depended.
Brooklyn Heights, 250 Years Later
The landscape of the battle has changed almost beyond recognition. Roads, neighborhoods, parks, and buildings now occupy ground once crossed by British regulars, Hessian troops, Continental soldiers, and militia.
Brooklyn Heights remains one of the names that connects the modern city to those August days in 1776.
Our Brooklyn Heights Tea commemorative tin takes its name from the position to which Washington's army retreated after the Battle of Long Island. Filled with Oolong tea, it is part of the Oliver Pluff & Co. Celebration Cities collection created to mark America's 250th anniversary.
