08/27/2026
250 years ago today, the Battle of Brooklyn, the largest battle of the War and a major Colonial defeat, began. This battle would prove monumental for Long Island, as the outcome led to a "wretched" and often violent British occupation and resistance through November 1783. Thousands of pro-Independence Long Islanders fled to upstate NY & Connecticut. Thousands of free and enslaved Black Colonials fled or escaped to British-held New York City.
In the end, thousands of Loyalists left the new country for Nova Scotia, England and the Caribbean. Over three thousand Black Colonials went with them, fleeing victorious Americans including George Washington, who wanted their slaves back.
While the Battle of Brooklyn was a major defeat, the Continental Army survived due to heroic efforts on the 27th by the Maryland 400, and days later by New England sailors who silently ferried the army across the East River to safety in Manhattan. The Army survived.
August 27, 1776 — The Battle of Long Island Begins
Two hundred and fifty years ago today, the British executed a carefully planned flanking maneuver and won the largest battle of the American Revolution to that point.
The plan had been approved the previous day after Loyalists informed Lieutenant General Sir Henry Clinton that Jamaica Pass—the easternmost route through the Guan Heights—was lightly guarded. Rather than attack the strongest American positions directly, Clinton proposed marching around them and striking from behind.
That evening, approximately 10,000 British troops began a secret nighttime march. Their campfires were left burning to suggest the army remained in place, while Loyalist guides led Clinton’s column along unfamiliar roads toward Jamaica Pass. The small American guard there was captured without firing a shot, leaving the route to the Continental flank open.
Meanwhile, General James Grant advanced with roughly 4,000 British and Hessian troops along the Gowanus Road. American forces commanded by Major General William Alexander, Lord Stirling, resisted across hills, orchards, bridges, and stone walls. Around Battle Hill, they briefly drove British troops from the summit and inflicted some of the heaviest British casualties of the day.
The fighting convinced the Americans that Grant’s assault was the main attack.
It was exactly what General William Howe intended them to believe.
At about 9:00 that morning, signal guns announced that Clinton’s column had completed its march and reached the American rear. Hessians under General Leopold von Heister advanced through Battle Pass while Clinton struck the Continental left and rear.
Major General John Sullivan’s command was caught between the converging forces. Having already sent troops toward Stirling’s position, Sullivan struggled to reorganize his men. Fierce fighting followed as the American line collapsed. Many soldiers escaped toward Brooklyn Heights, but Sullivan was captured.
Lord Stirling continued resisting until British troops appeared behind him. He then ordered his men to retreat across Gowanus Creek while approximately 260 Maryland soldiers under Major Mordecai Gist covered their withdrawal.
The Marylanders repeatedly charged superior British forces near the Vechte-Cortelyou House, now remembered as the Old Stone House. Their attacks allowed hundreds of Continental soldiers to escape, but nearly the entire covering force was killed or captured. Watching from the American lines, Washington reportedly exclaimed, “Good God, what brave fellows I must this day lose.”
Washington rushed reinforcements across the East River, but the battle had already been decided. By evening, the surviving Americans had withdrawn behind the fortifications at Brooklyn Heights.
Howe stopped short of storming those defenses. Remembering the heavy British losses at Bunker Hill, he began preparing for a formal siege. He believed Washington’s army was trapped against the East River, with British troops blocking escape by land and the Royal Navy expected to prevent evacuation by water.
The British had used intelligence, deception, local Loyalist assistance, and a disciplined night march to outflank and defeat the Continental Army. Yet Howe’s decision to halt outside Brooklyn Heights gave Washington one final opportunity to save it.
And that’s the way it was, August 27, 1776.
