The Battle of Long Island, a pivotal engagement in the American Revolutionary War, marked a significant British victory and a challenging moment for colonial resistance. Fought on August 27, 1776, this battle showcased military strategy, battle tactics, and the resilience of the Continental Army amid early war battles. Often referred to as the Battle of Brooklyn, it involved intense urban warfare, defensive tactics, and a strategic withdrawal that preserved George Washington’s forces for future fights in the quest for American independence. As part of the New York campaign, the clash highlighted British occupation tactics, Hessian involvement, and the evolving Revolutionary War strategy in the Eastern Theater.
This article provides a detailed explanatory overview, incorporating key elements like the Long Island campaign’s background, a battle map description, a comprehensive summary, casualties, outcome, and the Battle of Long Island significance, underscoring its historical significance in the American independence movement.
Background: The New York Campaign 1776 and Prelude to Conflict
The American Revolutionary War erupted in 1775 with clashes at Lexington and Concord, escalating into a full-scale struggle for American independence. By 1776, the British Army, under General William Howe, sought to crush colonial resistance by capturing key ports and cities. The New York campaign 1776 represented a strategic offensive to seize New York City, a vital hub due to its harbor and central location in the Eastern Theater. Howe’s forces, bolstered by Hessian mercenaries, aimed to isolate New England and demoralize the Patriots.
George Washington, commanding the Continental Army, anticipated the threat and moved his troops from Boston fresh from forcing the British evacuation in March 1776 to fortify New York. Washington’s retreat from earlier positions reflected cautious military leadership, but his army, comprising about 19,000 men including American militia, was undermanned and inexperienced. Defenses were constructed on Manhattan and Long Island, New York, with Brooklyn Heights serving as a key stronghold overlooking the East River. Key subordinates like Israel Putnam, John Sullivan, and William Alexander (Lord Stirling) managed sectors, while British commanders such as Charles Cornwallis and Henry Clinton planned the assault.

The British amassed over 32,000 troops on Staten Island by mid-August, supported by a formidable fleet. Washington divided his forces, placing about 9,000 on Long Island to guard against landings. The stage was set for a confrontation that would test Continental Army tactics against superior British invasion tactics, highlighting colonial military setbacks in Revolutionary War early battles.
When Was the Battle of Long Island?
The Battle of Long Island took place on August 27, 1776, with the main fighting occurring that day, though some sources extend it to August 29 due to subsequent maneuvers and the American evacuation. This date marked the largest single engagement of the Revolutionary War in terms of troop numbers, unfolding amid the sweltering summer heat of the 1776 military campaigns.
Battle of Long Island Map: Visualizing Terrain and Troop Movements
Understanding the Battle of Long Island requires examining its terrain through historical maps, such as those from Bernard Ratzer’s 1766-1767 surveys or modern reconstructions by the National Park Service. These maps depict Long Island, New York, as a strategic landscape with rolling hills, marshes, and passes that influenced battle tactics.
A typical overview map shows British forces (red lines) landing at Gravesend Bay in southwest Kings County, advancing northeast toward Brooklyn Heights. The Continental Army (blue lines) defended the Heights of Guan a ridge of hills up to 150 feet high stretching across the area, acting as a natural barrier to New York City across the East River.
Key locations include:
- Jamaica Pass: The lightly guarded easternmost pass, site of the British flanking maneuver, shown as a narrow road through wooded hills.
- Gowanus Creek: A marshy waterway and millpond in the southwest, where fierce Gowanus Creek fighting occurred during the retreat; maps illustrate its tidal marshes as obstacles.
- Brooklyn Heights: Elevated fortifications overlooking the East River, with Manhattan to the north; defensive lines are marked with earthworks and artillery positions.
- Battle Hill: The highest point at 220 feet, in modern Green-Wood Cemetery, depicted as a focal point of intense combat.
- Old Stone House (Vechte-Cortelyou House): A stone structure near Gowanus Creek, central to the Maryland 400’s stand.
- Flatbush Pass and Bedford Pass: Central passes where Hessian troops and British diversions attacked.

Troop movements on maps highlight Howe’s night march through Jamaica Pass, enveloping Sullivan’s and Stirling’s positions. Arrows show the American collapse and retreat to Brooklyn Heights, followed by the foggy evacuation across the East River to Manhattan. These visuals emphasize defensive tactics, urban warfare elements in the villages, and the role of terrain in the Jamaica Pass ambush, underscoring British military strategy in outflanking the Colonials.
Summary Battle of Long Island: A Detailed Explanatory Account
The Battle of Long Island, also known as the Battle of Brooklyn, was a masterful display of British military strategy that nearly destroyed the Continental Army early in the war. This detailed battle summary chronicles the events hour by hour, revealing the chaos, heroism, and tactical decisions that defined this Revolutionary battle.
Prelude and British Landing (August 22-26, 1776)
Following their arrival on Staten Island, the British under William Howe executed a flawless amphibious landing on August 22 at Gravesend Bay, southwest of Brooklyn. An advance guard of 4,000 men, led by Henry Clinton and Charles Cornwallis, disembarked unopposed, quickly reinforced to 15,000 troops with 40 artillery pieces. Washington, misjudging the main attack as targeting Manhattan, sent reinforcements to Long Island, bringing the total to about 9,000 under Israel Putnam after replacing John Sullivan.
The Americans fortified the Heights of Guan, a ridge with four key passes: Gowanus Road (west), Flatbush (center), Bedford (east-central), and Jamaica Pass (far east). Jamaica Pass was patrolled by only five militia officers a critical oversight. On August 24, Howe received 5,000 Hessian mercenaries under Leopold von Heister, swelling his force to 20,000. Washington visited Long Island, exhorting troops to fight for American patriotism.

On August 26, Howe finalized plans: a diversionary attack by James Grant on the American right (Gowanus), Hessians under von Heister on the center (Flatbush and Bedford), and a flanking march of 10,000 men under Clinton through Jamaica Pass to envelop the Americans.
Night March and Initial Clashes (August 26-27, 1776, Evening to Dawn)
At 9:00 p.m. on August 26, Clinton’s column began a silent 9-mile night march through Jamaica Pass, guided by Loyalist William Howard. The five American pickets were captured without alarm. By 3:00 a.m. on August 27, the British reached Bedford village undetected.
Meanwhile, at 11:00 p.m., Grant’s 4,000 Scots advanced toward Gowanus Pass, engaging American skirmishers around 1:00 a.m. near the Red Lion Inn the first shots of the battle. Lord Stirling, commanding 1,600 men including the Maryland and Delaware regiments, held the line against Grant.
Morning Envelopment and Collapse of the American Left (August 27, 1776, 8:00 a.m. – Noon)
At 8:30 a.m., two cannon shots from Grant signaled the attack. Hessians under von Heister assaulted Flatbush and Bedford Passes, pinning Sullivan’s 1,200 men. Clinton’s flanking force emerged behind Sullivan around 9:00 a.m., trapping the Americans in a pincer.
Sullivan’s troops, outflanked, fought desperately in the woods near Battle Pass (modern Prospect Park). Hand-to-hand combat ensued, with bayonets and musket butts. Sullivan was captured after his men scattered; about 400 Americans were killed or wounded here. The line crumbled, with survivors fleeing toward Brooklyn Heights.
On the right, Stirling held against Grant’s superior numbers. British grenadiers and Hessians pressed, but Stirling’s men repulsed several charges. Around 11:00 a.m., Cornwallis’s troops from the flanking column blocked Stirling’s retreat, surrounding his force near Gowanus Creek.
The Heroic Stand at Gowanus Creek and Old Stone House (August 27, 1776, Noon – Afternoon)
Stirling ordered a retreat across the marshy Gowanus Creek, but to cover it, he led 400 Maryland troops (actually 260-270) in six charges against Cornwallis at the Old Stone House. This rear-guard action, amid cannon fire and musket volleys, inflicted heavy British casualties but cost the Marylanders dearly 256 killed or captured, with units losing up to 80% of their men. Major Mordecai Gist and nine survivors escaped by swimming the creek. Stirling surrendered to von Heister around noon.

Washington, arriving from Manhattan, witnessed the rout from Brooklyn Heights. He famously exclaimed, “Good God, what brave fellows I must this day lose!” as he rallied fugitives. By afternoon, about 3,000 Americans had retreated to Brooklyn Heights’ fortifications, pursued by the British.
Siege of Brooklyn Heights and the Miraculous Evacuation (August 27-30, 1776)
Howe, cautious after Bunker Hill’s pyrrhic victory, halted the assault on Brooklyn Heights, opting for siege warfare. Trenches were dug, approaching within 600 yards by August 28. Washington reinforced to 9,500 men, holding a council that decided on evacuation.
On August 29, under cover of rain and fog, Colonel John Glover’s Marblehead mariners ferried the army across the East River to Manhattan. By 7:00 a.m. on August 30, all 9,000 troops, artillery, and supplies were evacuated without detection or loss a masterful American evacuation that saved the Continental Army from annihilation.
This detailed summary illustrates the battle’s phases: British flanking brilliance, colonial resistance at key points like Gowanus Creek fighting and Brooklyn Heights defense, and Washington’s strategic withdrawal, blending infantry clashes with elements of urban warfare in the villages and farms of Long Island.
Casualties of the Battle of Long Island
The casualties of the Battle of Long Island were lopsided, reflecting the British envelopment’s success. The Continental Army suffered approximately 300 killed, 800 wounded, and 1,079 captured or missing, totaling around 2,179 losses. Many prisoners endured harsh conditions on British prison ships in New York Harbor.
British and Hessian casualties were lighter: 64 killed (59 British, 5 Hessians), 294 wounded (268 British, 26 Hessians), and 31 missing, for a total of 389. The disparity underscored the effectiveness of British tactics and Hessian involvement, though the Maryland 400’s stand inflicted notable damage on elite units.
Who Won the Battle of Long Island?
The British won the Battle of Long Island decisively, achieving a tactical and strategic victory by routing the Continental Army and securing Long Island and New York City. William Howe’s forces drove the Americans from their positions, leading to the British occupation of New York, which they held until the war’s end in 1783. However, Washington’s successful retreat prevented a total catastrophe, allowing the Patriot resistance to continue.

Battle of Long Island Significance
The Battle of Long Island significance lies in its role as a major colonial military setback that nearly ended the Revolution early. As the largest of Revolutionary War early battles, with over 40,000 troops engaged, it demonstrated the British Army’s superiority in numbers, training, and strategy, particularly through the Jamaica Pass ambush and flanking maneuvers.
Strategically, the British victory enabled control of New York Harbor, a base for operations and British occupation New York throughout the war. It forced Washington into a series of retreats, including across New Jersey, but his evasion preserved the army, leading to later triumphs like Trenton and Princeton.
The battle boosted British morale but also revealed Howe’s caution, as he failed to pursue aggressively, allowing the American evacuation. For the Americans, it highlighted deficiencies in intelligence and militia reliability, prompting reforms in Continental Army tactics. The Maryland 400’s heroism became a symbol of American patriotism, inspiring future enlistments.
In the broader Revolutionary War legacy, Long Island underscored the war’s length and cost, shifting focus to guerrilla tactics and foreign alliances. Sites like Battle Hill and the Old Stone House preserve the Long Island battle legacy, commemorating Patriot resistance and the sacrifices in the American independence movement.
Conclusion
The Battle of Long Island, fought on August 27, 1776, epitomizes the challenges of the American Revolutionary War’s early phases. From the British victory and colonial retreat to Washington’s masterful evacuation, it showcased military strategy, defensive tactics, and the grit of the Continental Army against the British Army and Hessian troops.
Locations like Long Island, New York, Brooklyn Heights, Gowanus Creek, and Jamaica Pass remain etched in history as sites of intense Revolutionary battles. With casualties highlighting the conflict’s brutality, the battle’s outcome led to British occupation but also sowed seeds of American resilience. As a cornerstone of the New York campaign 1776, its historical significance endures, reminding us of the high stakes in colonial resistance and the path to American independence.