Who won the Battle of Long Island?
The Battle of Long Island, fought on 27 August 1776 near Brooklyn, was the largest battle of the American Revolution and a clear British victory. General William Howe outflanked Washington's army through a lightly guarded pass and drove it back to its defenses. But over the night of 29 to 30 August, Washington secretly evacuated his whole army across the East River to Manhattan, saving the Continental cause from destruction.3
In the summer of 1776, weeks after the Declaration of Independence, the largest expedition Britain had yet sent overseas fell on George Washington's young army at Brooklyn. He lost the battle badly, and then saved his army with one of the great escapes of the war.4
Part of The greatest battles of the American Revolution · Before: Battle of Bunker Hill · Next: The Battle of White Plains
The British descend on New York
After being driven from Boston, the British under William Howe landed a huge army and fleet at New York to crush the rebellion. Washington, guessing they would strike at the city, divided his forces to defend both Manhattan and the heights of Brooklyn on Long Island.
The Continental Army had marched from Boston in April and spent the spring fortifying the city and the heights of Brooklyn. The British fleet began arriving in late June, and by mid-August a large British and Hessian army was camped on Staten Island, brought over by a fleet under Howe's brother, Admiral Richard Howe.5
On 22 August the British began crossing unopposed to Gravesend Bay on Long Island. Washington, suspecting a feint aimed at Manhattan, was slow to shift troops to Brooklyn, and he had already lost the general he had chosen to command there: Nathanael Greene had fallen seriously ill, and the Long Island defenses passed to John Sullivan and then to Israel Putnam.6
How many soldiers fought at the Battle of Long Island?
Estimates run from about 30,000 to 40,000 men. The American Battlefield Trust counts some 20,000 British and Hessian troops engaged against about 10,000 Americans, and counts that include every unit on the island reach 40,000. On that basis the Trust calls it the largest battle of the Revolution; Brandywine, with about 30,000, comes next.7
The troops who met the first blow were far fewer. Only some 2,000 to 2,400 Americans held the wooded Heights of Guan in front of the main works, with about 6,000 more inside the Brooklyn forts, while Howe sent around 10,000 men on his flank march alone. The losses are well documented: about 300 Americans killed, 650 to 800 wounded and some 1,100 captured or missing, against 64 British and Hessian dead and roughly 315 to 325 wounded, missing or captured.8
The flank through Jamaica Pass
Howe pinned the American front with part of his army while marching the bulk of it by night around the American left, through the lightly guarded Jamaica Pass. At dawn the British appeared in the American rear, and the defense collapsed.9
The plan came from Henry Clinton, after local Loyalists told the British that Jamaica Pass, on the far left of the American line, was watched by just five militia officers. Late on 26 August about 10,000 men under Clinton, Charles Cornwallis and Howe himself set out along narrow back roads to seize the pass.10
At 9 a.m. James Grant's troops opened the diversion against Lord Stirling on the Gowanus Road, and Hessians under Philip von Heister pressed the center at Flatbush. When Clinton's column struck from behind, the American line between them broke. Sullivan was captured, and the bloodiest fighting of the day came at Battle Pass, where the Hessians closed with the bayonet.11
Defeat at Brooklyn
Caught between two forces, the Americans were routed, though a stand by Maryland troops bought time for many to escape to the main works. Washington's army fell back into its fortified lines on Brooklyn Heights, with the East River at its back and the British closing in.12
The stand that bought that time is remembered as the Maryland 400. With most of Stirling's men ordered back across Gowanus Creek, Major Mordecai Gist and a few hundred Marylanders, with Stirling himself, charged Cornwallis's troops near the Vechte-Cortelyou farmhouse again and again. About 256 Marylanders were killed or captured, and accounts put the number who regained the American lines at between seven and a dozen. Stirling surrendered to the Hessians.13
Many of the prisoners taken that day never came home. Americans captured in New York were held in sugar houses, churches and, above all, rotting ships in Wallabout Bay; over the whole war more than 11,000 Americans died as prisoners, more than were killed in battle.14
Why didn't Howe storm Brooklyn Heights?
Howe chose a siege over an assault. On the evening of 27 August he overruled officers who wanted to attack the American works at once and began digging approach trenches instead. Historians have long debated the decision, taken little more than a year after the costly British assault on entrenched Americans at Bunker Hill.15
The pause gave Washington two days. Storms and contrary winds kept British warships out of the East River, and with the enemy trenches creeping closer, Washington decided to abandon Long Island rather than risk the whole army.16
The night evacuation
Rather than risk a siege, Washington made a bold decision. Over the night of 29 to 30 August, under cover of darkness and a fortunate fog, his men were ferried across the East River to Manhattan in small boats, taking the whole army and nearly all its guns and stores, without the British realizing until it was done.17
The boats were handled by John Glover's Massachusetts regiment of Marblehead seamen. Working through the night against the tide, they rowed about 9,000 soldiers, with horses, wagons and artillery, from Brooklyn to Manhattan. A dense fog hid the last crossings, and when British patrols probed the lines they found them empty. Not a man had been lost.18
Why Long Island mattered
Long Island was a heavy defeat that soon cost Washington New York City, and he would be driven across New Jersey in the months that followed. But the escape preserved the army, and with it the Revolution, setting up the comeback at Trenton that winter.19
The rest of the New York campaign went the same way. On 15 September the British landed at Kip's Bay and Washington gave up the city. Glover's men delayed the next landing at Pell's Point in October, the armies met at White Plains, and on 16 November the garrison of Fort Washington surrendered. New York remained the main British base until 1783.20
Where was the Battle of Long Island fought, and what remains?
The battle was fought across what is now central Brooklyn, from the hills inside Green-Wood Cemetery and Prospect Park down to the marshes of Gowanus Creek. A few places mark it today: Battle Hill in Green-Wood, Battle Pass in Prospect Park, the Old Stone House in Washington Park and the Prison Ship Martyrs Monument in Fort Greene Park.21
Battle Hill, the highest point in Brooklyn, was fought over on the morning of 27 August; it is now part of Green-Wood Cemetery, which holds Battle of Brooklyn commemorations there. The Old Stone House is a reconstruction, completed in 1934 according to NYC Parks, of the farmhouse where the Marylanders made their charges. In Fort Greene Park a column about 150 feet high, designed by McKim, Mead and White, stands over a crypt holding remains of prisoners who died on the British ships; it was dedicated in 1908 in the presence of William Howard Taft.22
