Key figures: George Washington, William Howe, Henry Clinton, Lord Stirling (William Alexander), Israel Putnam, John Sullivan, Charles Cornwallis, Leopold von Heister, James Grant, John Glover, William Smallwood
Summary
The Battle of Long Island, also called the Battle of Brooklyn, was fought on August 27, 1776, in Brooklyn, New York. It was the largest engagement of the American Revolutionary War by troop numbers, pitting approximately 20,000 British and Hessian troops under General William Howe against around 10,000 Continental soldiers under General George Washington. The battle opened the British campaign to seize New York City and was the first major engagement after the Declaration of Independence.
Strategic Context and British Build-up
Following the British evacuation of Boston in March 1776, General Howe assembled a massive expeditionary force on Staten Island. By August 1776, the assembled force numbered approximately 32,000 troops — veterans of the Siege of Boston, newly arrived regiments from Ireland, and approximately 8,000 Hessian mercenaries hired from the Landgrave of Hesse-Kassel — supported by over 400 transport and warships, including 73 warships, under Admiral Lord Richard Howe. It was the largest British military force ever deployed in North America to that point. Washington, recognizing New York City’s strategic importance as a harbor and transit point, divided his approximately 20,000 available Continental soldiers between Manhattan and Long Island, placing Major General Israel Putnam in overall command of the Brooklyn defenses.
The American defensive line ran along the wooded Guan Heights ridge. Three roads breached it: the Gowanus Road on the western flank, the Flatbush Road through the center, and the Bedford Road in the east. A fourth route, the Jamaica Pass at the far eastern end, was patrolled by only five militia officers on horseback. Washington had approximately 3,000 troops deployed forward along the Heights, with 10,000 total on the Brooklyn side of the East River.
The British Landing and Approach: August 22–26
At 5:10 AM on August 22, the British advance guard landed unopposed at Gravesend Bay on the southern shore of Long Island. By noon, approximately 15,000 troops had come ashore; by August 25, additional units brought the total to 20,000. General Howe organized his assault into three coordinated columns. General James Grant commanded the western column on the Gowanus Road with approximately 5,000 men — his mission was to pin the American right flank under Lord Stirling (William Alexander). Hessian General Leopold von Heister commanded the center column on the Flatbush Road with approximately 5,000 troops, charged with pinning John Sullivan’s division at the central passes. General Henry Clinton commanded the main flanking column of approximately 10,000 men, including Cornwallis’s reserve.
Local Loyalists informed Clinton of the vulnerable Jamaica Pass. On the night of August 26, at approximately 9:00 PM, Clinton’s column began a silent night march eastward along the Jamaica Road. Five American sentries at the Jamaica Pass were captured without a shot at approximately 3:00 AM on August 27. By 9:00 AM, Clinton’s force had marched through the pass, swung northward through the hamlet of Jamaica, and was positioned behind the entire American line at the village of Bedford, having traveled roughly 14 miles overnight.
The Battle: August 27
Howe fired signal guns at 9:00 AM to initiate the simultaneous assault. Grant attacked up the Gowanus Road against Stirling’s approximately 1,600 troops, pinning them in place. Von Heister’s Hessians advanced on the Flatbush Road, engaging Sullivan’s division frontally with artillery. Sullivan, hearing the signal guns and realizing the threat at his rear, attempted to regroup but his forces were caught between von Heister’s frontal assault and Clinton’s flanking column closing from behind. Sullivan’s division was rapidly overwhelmed; Sullivan himself was captured in a cornfield.
Stirling, commanding the American right, recognized the encirclement closing around him. To allow the bulk of the forward Continental troops to escape north toward the Brooklyn lines, Stirling detached approximately 260–270 soldiers of the Maryland regiment under Colonel William Smallwood — sometimes called the “Maryland 400” — to conduct a rear-guard action at the Old Stone House (Vechte–Cortelyou House) on the Gowanus Road. The Maryland troops launched at least five separate charges against Cornwallis’s 2,000-man force at the house, allowing thousands of Continentals to escape across the marshy Gowanus Creek. The charges were suicidal in effect: approximately 256 Maryland troops were killed in the assaults, and fewer than a dozen returned to the American lines. Washington, observing the action from a rise at the Brooklyn fortifications, reportedly exclaimed that he feared the day was lost.
By mid-afternoon, the forward American positions had collapsed. Approximately 1,079 American soldiers were captured or missing, with around 300 killed. British and Hessian losses totaled approximately 64 killed, 293 wounded, and 31 missing. Among the American prisoners were Generals John Sullivan and Lord Stirling himself (captured by a Hessian detachment).
Howe’s Pause and the Brooklyn Evacuation: August 27–30
Howe elected not to assault the American fieldworks at Brooklyn Heights immediately, choosing instead to begin formal siege approaches on the night of August 27–28. His reasoning — that an assault on prepared fortifications would be costly and that siege operations were more professional — became a source of lasting controversy; the pause gave Washington a critical window.
By August 28, Washington had reinforced the Brooklyn Heights perimeter with additional troops from Manhattan, bringing his force there to approximately 9,000. Recognizing the untenable position — the British fleet threatened to cut off the East River crossing — Washington resolved on a secret withdrawal. On the evening of August 29, Colonel John Glover’s regiment of Marblehead, Massachusetts fishermen began ferrying troops across the roughly mile-wide East River using flat-bottomed boats commandeered from local docks. Strict silence was maintained: oars were muffled, horses’ hooves wrapped, and talking forbidden. A fortuitous northeast wind shifted to the southwest during the night, then a thick fog settled over the river around 2:00 AM on August 30, concealing the operation from British observation posts. By 7:00 AM on August 30, all approximately 9,000 Continental troops had crossed to Manhattan with their equipment, artillery, and supplies — without a single casualty. Washington crossed with the last boat.
Aftermath and Prison Ships
British forces occupied Long Island and, within weeks, New York City (September 15, 1776), which remained under British control for the duration of the Revolutionary War. Following the battle, Admiral Lord Richard Howe paroled American prisoner General John Sullivan and conveyed a peace overture to Congress; on September 11, 1776, Benjamin Franklin, John Adams, and Edward Rutledge met Howe on Staten Island in an unsuccessful peace conference — the last formal British attempt at reconciliation before full-scale hostilities continued. Howe demanded revocation of the Declaration of Independence; the American commissioners refused.
American prisoners fared catastrophically: confined initially aboard prison ships in Wallabout Bay (adjacent to the battle site) and in the Middle Dutch Church in Manhattan, they were systematically deprived of food and medical care. Smallpox, dysentery, and starvation killed thousands; historians estimate that more Americans died in British captivity on the New York prison ships during the war than in all the battles of the Revolution combined.
Continental Morale Collapse and Washington’s New Jersey Retreat
The months following Long Island constituted the most severe morale crisis of the Revolutionary War. Washington’s forces — approaching 20,000 in August — shrank to fewer than 5,000 effective soldiers by December 1776, with most enlistments expiring January 1, 1777. Fort Washington fell November 16, 1776, with 2,800 prisoners taken; Fort Lee fell two days later. Washington retreated across New Jersey as British and Hessian forces under Cornwallis occupied the colony and thousands of New Jersey civilians signed British protection oaths.
The Continental Congress’s fiscal position deteriorated in tandem: the New York campaign’s losses forced emergency currency emissions in November and December 1776, deepening the inflationary spiral already under way and raising questions whether the Continental Army could survive another campaign season.
Thomas Paine, serving as an aide during the retreat, wrote The American Crisis (first published December 19, 1776) opening with: “These are the times that try men’s souls.” Washington ordered it read aloud to his troops before the crossing at Trenton on December 25–26, 1776 — a surprise attack that killed or captured approximately 900 Hessian soldiers and reversed the post-Long Island narrative of inevitable British victory. The sequence of Long Island defeat, retreat through New Jersey, and the Trenton counterattack established a founding story of American resilience under pressure that was cited and commemorated throughout subsequent generations.
Significance
The Battle of Long Island demonstrated both the vulnerability of Washington’s Continental Army and his capacity for strategic improvisation under pressure. The British tactical victory gave Howe control of Long Island and set the stage for the fall of New York City. The nighttime evacuation across the East River was widely recognized as Washington’s greatest early-war decision; it kept the Continental Army intact and in the field, enabling future campaigns including the pivotal victories at Trenton and Princeton. The battle revealed persistent American weaknesses in reconnaissance — particularly the failure to adequately guard the Jamaica Pass — and in coordination between divisions. The sacrifice of the Maryland regiment at the Old Stone House became one of the war’s celebrated acts of rear-guard courage and is commemorated at the Vechte–Cortelyou House site in Brooklyn’s Prospect Park today. The British failure to press their advantage after the field victory, whether from caution or professional formality, allowed a nascent republic to survive its first major military test.