The Battle of Long Island



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The Battle of Long Island, which took place on Brooklyn Heights, Aug. 27, 1776, is the most important event in the history of the island with one of the largest expeditionary forces ever launched against an enemy in the history of Great Britain – 32,000 troops. The immensity of that military effort was a tribute both to the fighting skills of the Americans and the grand strategy of the British high command.

George Washington, anticipating an attack on New York, moved his 19,000 raw and poorly equipped soldiers, setting them to work building fortifications on the southern tip of Manhattan and in Brooklyn Heights.

On the morning of August 22, 1776. American stationed at Gravesend (near the present Bensonhurst section of Brooklyn) awoke to see an armada approaching from Staten Island, ships loaded to the gunwales with British troops. The invasion was on. The American fled and soon joined the bulk of Patriots soldiers who were aligned either behind the Brooklyn Heights fortifications or along a ridge that ran from near Gowanus Bay eastward toward Jamaica. The ridge, called the Heights of Guan, was thickly wooded and formed a natural barrier, penetrable only through four openings, the easternmost of which was called Jamaica Pass.

After several days of skirmishing, the British took up positions in front of the three other passages, engaging the attention of about 2,500 American militiamen defending the ridge. While Washington waited for the attack, General Howe led his main force of 10,000 on an all-night march to Jamaica Pass, where only five Patriot officers had been posted. Capturing the five before they could warn their cohorts, the British learned that the pass had been left undefended and quickly poured through. Howe’s strategy worked to perfection. He had positioned overwhelming forces both in front of and behind the American lines; the final blow was to be coordinated with a naval bombardment of Brooklyn Heights from the East River.

However, nature intervened. A stiff north wind and an ebbing tide prevented Howe from moving his fleet northward. Yet the situation was still desperate. Patriot troops, caught in the British pincers, suffered severely and were barely able to retreat behind the fortified Brooklyn Heights positions. There, they faced a force, superior in every regard, that was prepared to win victory by seige or assault.

Confronted by this terrible dilemma, Washington conceived and executed a brilliant strategem – to retreat to Manhattan. After sustaining incessant fatigue and constant watchfulness for two days and nights, attended by heavy rain, exposed every moment to an attack by a vastly superior force in front, and to be cut off from the possibility of retreat to New York by the fleet which might enter the East River, Washington commenced recrossing his troops from Brooklyn to New York on the night of Aug. 29.  

Moments before its completion, with Washington on the Long Island side, British scouts, suspicious of the silence, infiltrated the Patriot lines and discovered what was happening. But before they could act, a fog rolled in and concealed the departure of the remaining boats, one of which had Washington on board.

The evacuation resulted in the extrication of some 9,500 American soldiers out of 10,000 American actively engaged in the Battle of Long Island with their equipment and supplies, from positions only 600 yards from the British lines to safety in Manhattan. This was one of the first American defeats in the Revolutionary War.

Long Island remained a British stronghold until the end of the war in 1783.


Until next time. Stop and smell the roses.

Rosalinda, “The Rose Lady “