Sunday · September 27, 2026
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Howe crushes Washington's army on Long Island; Brooklyn Heights now under siege

A flanking march through Jamaica Pass catches the Continental Army's left wing off guard.

New York Harbor was the prize, and General William Howe had spent the summer massing troops on Staten Island to take it. On August 27, 1776, his army swung around the American left through an unguarded gap called Jamaica Pass and fell on Washington's positions from behind. The Continental Army, still raw and thinly spread along Brooklyn Heights, broke under the surprise attack, and the collapse made Long Island the largest battle of the Revolutionary War and its heaviest single defeat so far.

Brooklyn Heights, New York
The American Throughline

This was the first time an American army fought the British at full scale, and the defeat left thousands of Washington's men trapped against the East River with capture imminent. Washington's men learned, at cost, what it meant to face European regulars in open ground. After Long Island, Washington avoided pitched battles where his whole army could be trapped at once.

Did you know
QHow many prisoners did the British take at Long Island, including generals?

British and Hessian forces captured two American generals in the collapse: John Sullivan and William Alexander (known as Lord Stirling), who was noted for personally charging a Hessian regiment to buy time for his men to escape through the marshes, an act that cost his own freedom but let part of his brigade slip away. Both generals were eventually exchanged.

QWhere exactly did the British land before the battle began?

Howe's invasion force crossed from Staten Island in an amphibious landing onto Long Island days before the fighting, putting roughly twenty thousand men ashore, an operation the British carried out largely unopposed. That landing gave Howe time to scout the terrain and locate the gap at Jamaica Pass that decided the battle. The scale of the landing alone made Long Island the largest single deployment of troops seen in North America up to that point.

QWhat did Washington order his troops to do with New York's civilians before the fighting started?

Back in April, months before a shot was fired, Washington issued orders that his soldiers treat local civilians and their property with respect while the army built fortifications around the city. It was an unusual instruction for a force expecting siege and battle, showing Washington's early concern about keeping the population's trust.

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