The Battle of Long Island was a significant engagement on August 27, 1776, in the waters around Long Island in what is now Brooklyn, New York. The battle began at about 2:00 PM and ended near sunset. It was the first significant battle fought in the American Revolutionary War after independence had been declared on July 4, 1776. The British used land forces to conduct an amphibious assault near Plandome Road to seize Kips Bay from Continental Army forces commanded by Major General William Alexander, who retreated across Gravesend Bay for protection but was defeated by reinforcements under Admiral Sir George Rodney’s successful counterattack.
On August 23, 1776, General George Washington ordered Major General William Alexander of the Continental Army to evacuate his troops from New York City and retreat. Commander in Chief George Washington did not want to risk being trapped on Long Island if the British fleet gained control of New York Harbor. So on August 24, Alexander began moving several of his regiments by water across Long Island Sound to Pelham Bay.
On this day in 1776, Major General William Alexander began evacuating American troops from New York City. He attacked the British at Kips Bay on 25 August 1776. They retreated to New York on 29 August 1776.
On August 29, 1776, Admiral Sir Thomas Graves commanding the Royal Navy Fleet of the East (now HMS Victory), sailed out of New York Harbor to attack the retreating American troops. However, after reaching Gravesend Bay, Graves found that he could not make contact with his intended target.
After making several attempts at finding General Alexander’s force in Kips Bay, Admiral Graves resolved to launch an assault on Plandome Road across Long Island Sound between Little Neck and Flatbush. This would allow him to cut off Alexander’s path of retreat back across Long Island Sound into New York City.
At about 10:00 AM, Captain Thomas into Phipps anchored the 150-gun HMS Ruby in Gravesend Bay while Graves continued to seek out General Alexander’s retreating army.
An hour later, HMS Juno was sent to Pelham Bay under Captain Charles Holmes. At 11:30 AM, Admiral Graves ordered the sailing ship, HMS Pelican, to follow Holmes into Pelham Bay. Thus, the two boats began their fleets crossing Long Island Sound.
The British fleet of six sail of the line soon ranged across Kips Bay and turned toward Plandome Road at about 2:00 PM, with Admiral Graves’ flagship carrying “the flag of Vice-Admiral Governeur Schuyler.
Thus the British had a superior force of eight ships to oppose Alexander’s six ships of the line. The British fleet also had three smaller vessels with them. For the Americans, they had one ship, USS “Peggy.” They also had Fort George at Brooklyn and Fort Putnam and Fort Lafayette in Manhattan that succeeded in firing on and damaging HMS Juno but failed to hit it with any shot.
The Americans remained on Plandome Road until about 3:30 PM, when they attempted to retreat across Gravesend Bay. Alexander’s troops had no choice but to withdraw in the face of the superior forces.
The British, in turn, followed Alexander’s troops out of Kips Bay and across Gravesend Bay, arriving at Plandome within about an hour. After the Americans had successfully crossed into Pelham Bay, they continued retreating toward New York City for an hour when they were attacked again by HMS Peony under Captain Nassau Guy. They fired on USS “Peggy” at long range, causing it to set sail for Plandome.
After successfully crossing the Narrows under heavy fire from HMS Juno and HMS Brandon, Alexander ordered his men back into Brooklyn after their attempt to retreat across Gravesend Bay failed again.
The British continued to pursue Alexander’s troops down the eastern shore of Long Island. In his report, Admiral Graves made the following observation:
After they stopped in Pelham Bay, Admiral Graves moved his flagship to a safe distance from the shore and sent a boat ashore with a flag of truce. The Americans stood their ground and refused to surrender even after being informed that they were surrounded by 16,000 British. General Washington returned to Manhattan to send reinforcements across the East River, while Major General William Heath commanded Fort Washington.
The British were fully expecting Alexander’s troops to continue retreating across Long Island Sound. To their surprise, they found out that Alexander had already returned to Brooklyn. He had also sent a sizeable contingent to Manhattan and another sizable one across the East River into Queens after General Washington’s orders. Graves then realized that he had been completely fooled and that the Americans were receiving reinforcements. After sunset, he decided to withdraw his fleet, exiting Long Island Sound through Hell Gate by 2:00 AM on August 30, 1776.
However, due to adverse winds off Fire Island, the British fleet could not re-enter New York Harbor until 12:30 PM on August 31. Admiral Graves’ fleet had successfully crossed the Narrows but had to undergo many delays. Graves could not leave until 3:00 PM, long after the American forces had already started to retreat toward Brooklyn. This resulted in an unplanned attack on East Rock that morning by General Washington’s troops.
Admiral Montague decided against sending troops back across Long Island Sound to join General Howe’s troops at Staten Island to mount a second offensive against the American forces. Instead, he decided to withdraw his fleet back through Hell Gate by 2:00 AM Tuesday, August 30. The British navy spent the night transporting reinforcements across Staten Island and New York Harbor to confront the Americans at Whitehall Point.
The Americans had resumed their retreat towards Brooklyn around 2:00 AM on August 30. General Washington had kept General Heath in charge of defending Whitehall Point.
A messenger was sent out to inform Graves that the American troops were still in New York City. The British fleet then returned to Staten Island, but they did not arrive there until 6:00 AM on August 30. They then launched an attack against the American forces across East River at Whitehall Point at about 11:00 AM. However, they soon found out that the Americans had retreated again by 1:00 PM after hearing that General Howe’s troops were defeated at Kip’s Bay.