American Revolution: Battle of Long Island

Battle of Long Island
Battle of Long Island by Alonzo Chappel. Public Domain

The Battle of Long Island was fought August 27-30, 1776 during the American Revolution (1775-1783). Following his successful capture of Boston in March 1776, General George Washington began shifting his troops south to New York City. Correctly believing the city to be the next British target, he set about preparing for its defense. This work had commenced in February under the guidance of Major General Charles Lee and continued under the supervision of Brigadier General William Alexander, Lord Stirling in March. Despite the efforts, a lack of manpower meant that the planned fortifications were not complete by late spring. These included a variety of redoubts, bastions, and Fort Stirling overlooking the East River.

Reaching the city, Washington established his headquarters in the former home of Archibald Kennedy on Broadway near Bowling Green and began devising a plan to hold the city. As he lacked naval forces, this task proved difficult as New York's rivers and waters would permit the British to outflank any American positions. Realizing this, Lee lobbied Washington to abandon the city. Though he listened to Lee's arguments, Washington decided to remain at New York as he felt the city possessed significant political importance.

Armies & Commanders



Washington's Plan

To defend the city, Washington divided his army into five divisions, with three at the south end of Manhattan, one at Fort Washington (northern Manhattan), and one on Long Island. The troops on Long Island were led by Major General Nathanael Greene. A capable commander, Greene was struck down by with fever in the days before the battle and command devolved to Major General Israel Putnam. As these troops moved into position, they continued work on the city's fortifications. On Brooklyn Heights, a large complex of redoubts and entrenchments took shape that included the original Fort Stirling and ultimately mounted 36 guns. Elsewhere, hulks were sunk to deter the British from entering the East River. In June the decision was made to construct Fort Washington at the northern end of Manhattan and Fort Lee across in New Jersey to prevent passage up the Hudson River.

Howe's Plan

On July 2, the British, led by General William Howe and his brother Vice Admiral Richard Howe, began arriving and made camp on Staten Island. Additional ships arrived throughout the month adding to the size of the British force. During this time, the Howes attempted to negotiate with Washington but their offers were consistently rebuffed. Leading a total of 32,000 men, Howe prepared his plans for taking New York while his brother's ships secured control of the waterways around the city. On August 22, he moved around 15,000 men across the Narrows and landed them at Gravesend Bay. Meeting no resistance, British forces, led by Lieutenant General Lord Charles Cornwallis, advanced to Flatbush and made camp.

Moving to block the British advance, Putnam's men deployed onto a ridge known as the Heights of Guan. This ridge was cut by four passes at Gowanus Road, Flatbush Road, Bedford Pass, and Jamaica Pass. Advancing, Howe feinted towards Flatbush and Bedford Passes causing Putnam to reinforce these positions. Washington and Putnam hoped to entice the British into mounting costly direct assaults on the heights before pulling their men back into the fortifications on Brooklyn Heights. As the British scouted the American position, they learned from local Loyalists that Jamaica Pass was only defended by five militiamen. This information was passed to Lieutenant General Henry Clinton who devised an attack plan using this route.

The British Attack

As Howe discussed their next steps, Clinton had his plan for moving through Jamaica Pass at night and flanking the Americans put forward. Seeing an opportunity to crush the enemy, Howe approved the operation. To hold the Americans in place while this flank attack was developing, a secondary attack would be launched near Gowanus by Major General James Grant. Approving this plan, Howe set it in motion for the night of August 26/27. Moving through Jamaica Pass undetected, Howe's men fell upon Putnam's left wing the following morning. Breaking under British fire, American forces began retreating toward the fortifications on Brooklyn Heights (Map).

On the far right of the American line, Stirling's brigade defended against Grant's frontal assault. Advancing slowly to pin Stirling in place, Grant's troops took heavy fire from the Americans. Still not fully grasping the situation, Putnam ordered Stirling to remain in position despite the approach of Howe's columns. Seeing disaster looming, Washington crossed to Brooklyn with reinforcements and took direct control of the situation. His arrival was too late to save Stirling's brigade. Caught in a vise and fighting desperately against overwhelming odds, Stirling was slowly forced back.  As the bulk of his men withdrew, Stirling led a force Maryland troops in rearguard action that saw them delay the British before being captured.

Their sacrifice allowed the remainder of Putnam's men to escape back to Brooklyn Heights. Within the American position at Brooklyn, Washington possessed around 9,500 men. While he knew that the city could not be held without the heights, he was also aware that Admiral Howe's warships could cut his lines of retreat to Manhattan. Approaching the American position, Major General Howe elected to begin building siege lines rather than directly assaulting the fortifications. On August 29, Washington realized the true danger of the situation and ordered a withdrawal to Manhattan. This was conducted during the night with Colonel John Glover's regiment of Marblehead sailors and fisherman manning the boats.


The defeat at Long Island cost Washington 312 killed, 1,407 wounded, and 1,186 captured. Among those captured were Lord Stirling and Brigadier General John Sullivan. British losses were a relatively light 392 killed and wounded. A disaster for American fortunes in New York, the defeat at Long Island was the first in a string of reverses which culminated in the British capture of the city and surrounding area. Badly defeated, Washington was forced retreat across New Jersey that fall, finally escaping into Pennsylvania. American fortunes finally changed for the better that Christmas when Washington won a needed victory at the Battle of Trenton.

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Your Citation
Hickman, Kennedy. "American Revolution: Battle of Long Island." ThoughtCo, Aug. 27, 2020, Hickman, Kennedy. (2020, August 27). American Revolution: Battle of Long Island. Retrieved from Hickman, Kennedy. "American Revolution: Battle of Long Island." ThoughtCo. (accessed March 28, 2023).