OTD in History… August 27, 1776: The Battle of Long Island

Washington’s Greatest Defeat and America’s Hour of Liberty

By Bonnie K. Goodman, BA, MLIS

On this day in history… August 27, 1776, less than two months after declaring independence, the Continental Army faced its most severe test. The Battle of Long Island, also called the Battle of Brooklyn, was the first major engagement after the Declaration of Independence and the largest of the entire Revolutionary War. The British Empire dealt George Washington and his ill-prepared army a humiliating defeat in a single day. However, stories of sacrifice, courage, and survival emerged from this disaster, preserving the Revolution itself.

The British Arrive

When the British fleet appeared in New York Harbor in late July, it stunned the city. By some estimates, 400 ships and nearly 32,000 troops arrived under the command of General William Howe and his brother Admiral Richard Howe. The combined army and navy formed the largest expeditionary force Britain had ever sent abroad.

Historian David McCullough describes the scene in his book, 1776: “It was the greatest armada ever seen in American waters—greater than any the world had ever known… It was as if all London were afloat.” (1776)

Historian David Hackett Fischer laid out the scene in his book, Washington’s Crossing: “By late August two-thirds of the British army were in the colonies. Supporting these troops were seventy British warships in American waters, half the fighting strength of the Royal Navy. In 1776, it was the largest projection of seaborne power ever attempted by a European state.”

Henry Knox, Washington’s artillery commander, warned his wife Lucy on July 8: “The eyes of all America are upon us, the matters which we are to act are of infinitely high import… we shall probably have the largest and best appointed army in the whole world against us.” (Knox, Gilder Lehrman)

The imbalance was staggering. Washington commanded about 19,000 men spread across Manhattan and Long Island, many of them militia with little training. The fate of the Revolution suddenly hinged on a vulnerable position.

Defending New York

Washington had predicted that New York would be Britain’s prime target. Its deep harbor allowed naval dominance, and controlling the Hudson River would divide New England from the southern colonies. Yet his defensive preparations were flawed.

Historian Alexander Graydon later admitted, “The place in the lines… was low and unfavourable for defence… the enemy… entirely enclosed the whole of our position.” (Memoirs of His Own Time, 1846)

Washington split his forces, leaving part in Manhattan and part in Brooklyn. Entrenchments were built on Brooklyn Heights, but the outer defenses stretched too thin across wooded hills and farmland.

The Battle Begins

On August 22, British troops landed at Gravesend Bay, Long Island. Over the next four days, Howe carefully advanced, using deception and superior intelligence. Most crucially, he exploited the unguarded Jamaica Pass, a narrow road through the hills known only to locals. Loyalist farmers guided the British troops through the area at night, which allowed them to outflank the American left flank.

At dawn on August 27, Washington’s forces awoke to disaster. British troops under General Henry Clinton and Hessian mercenaries under General Leopold von Heister attacked from the front, while Howe’s men stormed from behind. The Americans, trapped between superior numbers, panicked and broke.

One soldier recalled the chaos: “We were attacked on all sides… the cannon played incessantly, the musketry poured in upon us like hail.” (McCullough, 1776)

The Maryland 400 and Lord Stirling

Despite the day's overwhelming defeats, instances of heroism also emerged. At the Old Stone House, near Gowanus Creek, Lord Stirling (William Alexander) commanded 2,000 men, including the famed Maryland Regiment. Facing nearly 10,000 British troops, Stirling ordered his men to charge.

The “Maryland 400” made six desperate assaults against entrenched British positions. Twice they recaptured the stone house, but each time were repelled. Of the roughly 400 Marylanders, only 96 survived.

Historian Thomas W. Field, writing in 1869, compared their sacrifice to Thermopylae:

“It was an hour more precious to liberty than any other in history.” (Battle of Long Island, 1869)

Their stand bought Washington’s army the time it needed to retreat across the marshes. Stirling himself was captured, but his valor became legendary. A contemporary newspaper called him “the bravest man in America.”

Washington’s Anguish

Washington, observing the rout from Brooklyn Heights, was devastated. Joseph Reed, his aide, recalled, “He wrung his hands, exclaiming repeatedly, ‘Good God! What brave fellows I must this day lose!’” (Reed, quoted in Freeman, George Washington: A Biography) The defeat was total: about 1,000 American casualties compared to 400 British losses. But the worst danger was that Washington’s entire army was trapped on Brooklyn Heights, cut off with the East River at their backs.

The Great Escape

Here Washington showed his genius, not in victory, but in survival. On the stormy night of August 29–30, he ordered a full evacuation. Using boats commandeered from local sailors, the Continental Army slipped silently across the East River to Manhattan. The retreat was nearly miraculous. A heavy fog rose that morning, concealing the last boats until every man was safely across. Washington himself boarded only after the final soldier had left.

In a letter to John Hancock, he admitted the difficulty, “I am sensible a retreating Army is encircled with difficulties… but when the Fate of America may be at Stake… I cannot think it safe or wise to adopt a different System.” (Washington to Hancock, Sept. 8, 1776, Founders Online) The Revolution survived by a thread.

The Aftermath

The British occupied New York City for the rest of the war, turning it into a base of operations and prison for thousands of American captives. Many prisoners perished on prison ships anchored in Wallabout Bay — grim reminders of the defeat. Historian David Hackett Fischer argues that the battle “demonstrated both the weakness and the resilience of the American cause.” (Washington’s Crossing, 2004) Certainly, while Washington lost New York, he preserved his army. The Continental Army lived to fight at Trenton, Princeton, and beyond.

Memory and Meaning

The Battle of Long Island remains a paradox: a devastating military loss but a moral victory of survival. It proved that the Revolution would not be won in a single glorious battle, but through endurance. It gave rise to legends: the Maryland 400, Lord Stirling, and Washington’s calm resolve. It showed that leadership sometimes means retreating wisely rather than fighting recklessly. Historian Thomas Fleming wrote, “The battle was lost, but the cause was not. In the gathering darkness, Washington’s genius saved the Revolution.” (Liberty! 1997)

Conclusion

On that summer day in Brooklyn, the Revolution nearly ended before it truly began. The British proved their power, but Washington proved his resilience. The sacrifice of the Marylanders, the anguish of Washington, and the providential escape under fog all became part of America’s founding story. As Thomas Field declared in his book, “The Battle of Long Island,” the stand at Brooklyn was “It was an hour more precious to liberty than any other in history.” From the ashes of defeat, the Revolution endured.

Sources

• Field, Thomas W. The Battle of Long Island: With Connected Preceding Events, and the Subsequent American Retreat. Brooklyn: Long Island Historical Society, 1869.
• Fischer, David Hackett. Washington’s Crossing. New York: Oxford University Press, 2004.
• Fleming, Thomas. Liberty!: The American Revolution. New York: Viking, 1997.
• Freeman, Douglas Southall. George Washington: A Biography. New York: Charles Scribner’s Sons, 1948.
• Graydon, Alexander. Memoirs of His Own Time; With Reminiscences of the Men and Events of the Revolution. Philadelphia: Lindsay & Blakiston, 1846.
• Knox, Henry. Letter to Lucy Knox, July 8, 1776. In The Gilder Lehrman Collection. New York: Gilder Lehrman Institute of American History. https://www.gilderlehrman.org/history-resources/spotlight-primary-source/henry-knox-british-invasion-new-york-1776.
• McCullough, David. 1776. New York: Simon & Schuster, 2005.
• Reed, Joseph. Letter on Washington at Brooklyn, August 1776. Quoted in Douglas Southall Freeman, George Washington: A Biography.
• Washington, George. Letter to John Hancock, September 8, 1776. In Founders Online, National Archives. https://founders.archives.gov/documents/Washington/03-06-02-0203.
• — — — . General Orders, August 1776. In Founders Online, National Archives. https://founders.archives.gov/documents/Washington.
• “Battle of Long Island.” History.com. A&E Television Networks, August 27, 2019. https://www.history.com/this-day-in-history/august-27/the-battle-of-brooklyn.
• “The Battle of Brooklyn.” TIME Magazine, August 27, 2019. https://time.com/5617055/battle-of-brooklyn/.

Bonnie K. Goodman, BA, MLIS, is a historian, librarian, journalist, and artist. She is the author of “On This Day in History…: Significant Events in the American Year,” and “A Constant Battle: McGill University’s Complicated History of Antisemitism and Now anti-Zionism.” She has a BA in History and Art History and a Masters in Library and Information Studies from McGill University. She has done graduate work in Jewish history at Concordia University as part of the MA in Judaic Studies and at the Hebrew University of Jerusalem as part of their MA in Jewish Education. She contributed to the “History of American Presidential Elections, 1789–2008,” edited by Gil Troy, Arthur M. Schlesinger, and Fred L. Israel (2012). She is the former Features Editor at the History News Network and reporter at Examiner.com, where she covered politics, universities, religion, and news. Her scholarly articles can be found on Academia.edu.