Battle of Long Island
The Battle of Long Island on 27 August 1776 was the largest engagement of the American Revolutionary War and came close to ending it. General William Howe's British and Hessian force of approximately 22,000 men — landed at Gravesend Bay on 22 August — faced roughly 10,000 Continental and militia troops under Washington defending a ridge of wooded hills (the Heights of Guan) across the Brooklyn waterfront. Washington's defensive plan left Jamaica Pass — the easternmost gap through the ridge — guarded by only five mounted officers. Howe sent a column of 10,000 men under Clinton and Cornwallis on a night march through Jamaica Pass, emerging behind the American left flank at dawn on 27 August while Hessians and British forces attacked frontally. The Americans were caught in a vice. General Stirling's Maryland brigade fought a desperate rearguard on the Gowanus Road, sacrificing itself to buy time for the main force to retreat to the Brooklyn Heights entrenchments. Maryland lost 400 men — Washington reportedly watched from the heights saying 'Good God, what brave fellows I must this day lose.' The Americans suffered approximately 300 killed and 1,100 taken prisoner. Howe declined to storm the Brooklyn Heights, preferring to open formal siege approaches — a decision that gave Washington his opening. On the night of 29–30 August 1776, under cover of fog and in complete silence, Washington evacuated approximately 9,000 men, their horses, cannon, and supplies across the East River to Manhattan — one of the most remarkable retrograde operations in military history. British sentries heard nothing; by dawn the evacuation was complete. Howe's decision not to storm the heights remains one of history's most debated military choices. Had he attacked on 28 August, the Continental Army would likely have been destroyed and the revolution extinguished. His failure to press his advantage at Long Island established a pattern that would recur throughout the campaign.
- Year: 1776 CE
- Category: Military
