Battle of Long Island (1776): Washington's Defeat and Escape

The Battle of Long Island, also called the Battle of Brooklyn, was fought on 27 August 1776 on the western end of Long Island, New York. A British army under General William Howe outflanked and defeated George Washington’s Continental Army in the first major battle after the Declaration of Independence. It is usually described as the largest battle of the American Revolutionary War by the number of troops involved, and it was followed by one of the war’s most remarkable escapes.

Background

After the British left Boston in March 1776, Washington expected them to strike next at New York. The city controlled the mouth of the Hudson River and one of the best harbours in North America. He moved most of his army there and began fortifying Manhattan and Brooklyn Heights, the high ground on Long Island that overlooked the city across the East River.

The British gathered an enormous force. From early July General William Howe landed troops on Staten Island, and his brother, Admiral Richard Howe, arrived with a large fleet. By August the British had assembled some 30,000 soldiers, including several thousand German troops, mostly from Hesse-Kassel, together with hundreds of ships. It was the largest expeditionary force Britain had sent overseas up to that time.

Washington had perhaps 19,000 to 23,000 men in the New York area, many of them inexperienced militia, and he had to divide them between Manhattan and Long Island. His most able subordinate on Long Island, Nathanael Greene, fell seriously ill in mid-August. Command there passed first to John Sullivan and then to Israel Putnam, neither of whom knew the ground well.

The British landing and the American line

On 22 August the British began landing at Gravesend Bay on the south-western shore of Long Island, eventually putting ashore about 20,000 men. The Americans had around 10,000 troops on Long Island, most of them inside the fortified lines on Brooklyn Heights. Some 3,000 were posted in front of these lines along the Heights of Guan, a steep wooded ridge that crossed the island from east to west.

Several roads ran through passes in the ridge. The Americans guarded the western passes at Gowanus, Flatbush and Bedford, but the easternmost route, Jamaica Pass, was watched by only five mounted militia officers. Local Loyalists told the British about this weakness, and General Henry Clinton proposed a wide flanking march to exploit it.

The battle

On the night of 26–27 August a column of about 10,000 men under Clinton, accompanied by Howe and Lord Cornwallis, marched quietly eastwards and then north to Jamaica Pass. They captured the five officers guarding it without a shot. By around 9 a.m. on 27 August the column had reached Bedford, behind the American left, and fired signal guns.

Meanwhile, British troops under General James Grant had begun a diversionary attack on the American right along the coast road near Gowanus, and Hessian troops under General Leopold Philip von Heister pressed the centre at Flatbush. Once the flanking column appeared in their rear, the American troops in the centre under Sullivan were caught between two forces. Many were killed or captured, and Sullivan himself was taken prisoner.

On the right, General William Alexander, who claimed the Scottish title of Lord Stirling, found himself cut off. To give his men time to escape across Gowanus Creek, he led about 400 Maryland soldiers, under the field command of Major Mordecai Gist, in repeated attacks against a much larger British force near the Vechte–Cortelyou house, now known as the Old Stone House. Most of the Marylanders were killed, wounded or captured, and Stirling was taken prisoner, but many of the other troops reached safety. The episode is remembered as the stand of the “Maryland 400”.

By early afternoon the survivors were back inside the Brooklyn lines. Howe chose not to storm the works at once, preferring to begin formal siege approaches, a decision that historians have long debated.

The night evacuation

Washington, who had crossed over from Manhattan during the battle, now had about 9,000 men penned against the East River with the British digging trenches before them. If the British fleet entered the river, the whole force could be trapped. On 29 August a council of war agreed to withdraw.

That night, in rain and wind that at first hampered the boats, regiments of Massachusetts fishermen and sailors from Marblehead, under Colonel John Glover, and from Salem, under Colonel Israel Hutchinson, began ferrying the troops across to Manhattan. Units left the lines one by one, while others stayed to keep up the appearance of a full garrison. When daylight came on 30 August the operation was not finished, but a thick fog settled over Brooklyn and covered the final crossings. Washington is said to have been among the last to leave. Almost the whole army, with most of its equipment, escaped.

Key people

George Washington commanded the Continental Army and made the costly decision to defend Brooklyn with a divided force, but his handling of the evacuation was widely praised. William Howe, the British commander-in-chief, won a clear victory but was later criticised for not pressing his advantage against the Brooklyn lines. Henry Clinton devised the flanking march that decided the battle. On the American side, John Sullivan and William Alexander, Lord Stirling, were both captured and later exchanged; Stirling’s sacrifice of the Maryland troops became one of the best-remembered acts of courage of the campaign.

By the numbers

Timeline

• 1776, 2 July: British troops begin landing on Staten Island.
• 1776, 22 August: The British land at Gravesend Bay, Long Island.
• 1776, 26–27 August (night): Clinton’s column marches through Jamaica Pass.
• 1776, 27 August: The Americans are defeated; Sullivan and Stirling are captured.
• 1776, 29–30 August (night): Washington evacuates his army across the East River.
• 1776, 11 September: Peace talks on Staten Island between Lord Howe and a congressional delegation fail.
• 1776, 15 September: British troops land at Kip’s Bay and take New York City.

Consequences and legacy

The defeat opened New York to the British, who occupied the city on 15 September 1776 and held it until November 1783. Washington’s army was pushed out of Manhattan and then across New Jersey, a retreat that ended only with the surprise victory of Washington’s crossing of the Delaware and the Battle of Trenton. Thousands of American prisoners taken in New York suffered terribly on British prison ships moored in Wallabout Bay, where many thousands died over the course of the war.

Today the battle is commemorated in Brooklyn by a reconstruction of the Old Stone House in Park Slope and by monuments in Prospect Park and Green-Wood Cemetery, which covers part of the battlefield.

Why it matters

The Battle of Long Island showed that the Continental Army could not yet match British regulars in open battle. Yet the escape across the East River preserved the army, and with it the Revolution. Washington learned to avoid risking his entire force in a single engagement, a lesson that shaped his strategy for the rest of the war.