After evacuating Boston, the British reorganized and focused their efforts on New York. When everything was ready, they made their first attempt on Long Island. This was preferred to New York, as it abounded with those supplies which their forces required.
During June through early August, the British forces concentrated around New York. At the time, New York was the largest city in the colonies. Lt. Gen. William Howe was the new Commander-in-Chief of the American colonies. He led a naval armada to Sandy Hook, New Jersey. This guarded the southern entrance to New York harbor. Adm. Richard Howe came and brought with him additional British troops and 150 more ships. Augmenting these forces, Maj. Gen. Henry Clinton brought even more troops and ships. This brought a British force of nearly 40,000 troops and several hundred warships. They were finally ready to attack the Patriots and hopefully end the rebellion.
Gen. George Washington anticipated that the British would move to and attack New York. His mission was to hold both New York City and Brooklyn. A defensive network around the harbor was soon established, which was a series of forts and interconnecting trenches. Brig. Gen. nathanael Green was given the job of the defense's architect. Greene concentrated his resources in a line anchored by 3 small forts along Guian Heights (also called Brooklyn Heights). The line was reinforced by felled trees. It offered a 3 mile barrier along a natural neck of strategic terrain that would have to be taken if New York was to be threatened by a British ground assault.
By August, a number of recruits joined the Patriots, bringing the total number of troops to around 19,000 men. Howe learned from local intelligence that the Patriots were deployed in defensive positions along Brooklyn Heights. He also learned of the weaknesses in the Patriots lines and planned to exploit them.
On August 20, Greene fell sick and was replaced by Brig. Gen. John Sullivan.
On August 22, early in the morning, Howe led a group of 20,000 troops in an amphibious assault against Long Island. The initial 4,000-man force left Staten Island and landed on the southwest side of Long Island without opposition between the two small towns of New Utrecht and Gravesend. The remainder of the force followed them during an intense naval bombardment. By 12:00 P.M., more than 15,000 troops and dozens of artillery pieces were ashore at Long Island. At the time of the landing, Washington was in New York City and was unsure of the landings were the main assault or only a diversion.
On August 23, a sharp skirmish occured between the British and the Patriot advance guard about 4 miles inland at Flatbush.
On August 24, Sullivan was replaced by Maj. Gen. Israel Putnam. Unfortunately, Putnam knew little about the terrain of Long Island. Being in charge of the island's defenses, this would come back to haunt the Patriots in the coming battle. He was tasked with overseeing two defensive lines perpendicular to one another. The main line contained about 6,500 troops and were deployed around Brooklyn and faced southeast. This line ran north for 1.5 miles from the mill dam-Gowanus Creek area that emptied into Gowanus Bay to Wallabout Bay. The remaining 3,000 troops were deployed to guard four strategic passes cut by major roads leading to the top and beyond the heights.
About 550 troops were on the far left guarding Gowanus Road overlooking Gowanus Bay. About 1.5 miles to the east were 1,100 troops guarding Flatbush Pass. Farther east for 1 mile were 800 troops guarding Bedford Pass. Still farther east of the left flank of Putnam's line were 500 riflemen. Their job was picketing a small line stretching toward Howard's Tavern at Jamacia Pass.
On August 25, additional British troops landed southeast of Denyse's Point. This brought the total number of British on Long Island to 20,000 men. Howe then split his force into two 10,000-man wings.
On August 26, in the evening, Lt. Gen. Leopold P. von Heister took post at Flatbush with his Hessian force. In the following night, the larger part of the British army, commanded by Clinton, marched to gain the road leading round the easterly end of the hills to Jamaica, and to turn the left of the Americans. He arrived about 2 hours before day, within half a mile of this road. One of his parties fell in with a patrol of American officers, and took them all prisoners, which prevented the early transmission of intelligence. Upon the first appearance of day, Clinton advanced and took possession of the heights over which the road passed. Brig. Gen. ?? Grant, with the left wing, advanced along the coast by the west road, near the narrows; but this was intended chiefly as a feint.
The guard which was stationed at this road, fled without making any resistance. A few of them were afterwards rallied, and Brig. Gen. William Alexander (Lord Stirling) advanced with 1,500 men, and took possession of a hill about 2 miles from the Patriot camp, and in front of Grant.
Howe was finally in position and ready to launch his offensive against the Patriots. Howe's plan was to send Brig. Gen. James Grant to the Patriot far right flank above Gowanus Bay to divert attention to the western end of the line. In conjunction with Grant, von Heister would move against and hold in place the Patriot center around Flatbush. While the Patriots focused their attention on their center-right, Howe would march east and then north with 10,000 troops beyond and behind Putnam's left flank. Howe would then roll up and crush the Patriots strung out along the high ridge.
On August 27, just after midnight, Grant led his 5,000-man column north along the Gowanus Road and began skirmishing with the Patriots.
At 3:00 A.M., Putnam was told of the British movement and he ordered Alexander to advance to the far right with reinforcements. Alexander deployed about 1,600 troops to meet Grant's troops. Grant stopped in front of the Patriot line and began firing his artillery. Meanwhile, Sullivan had reached the center of the line near Flatbush Pass, where he found von Heister's Hessians firing artillery. Sullivan sent troops west to reinforce Alexander.
At 8:00 A.M., Washington arrived on Long Island. When the British attacked the Patriot right and center, Col. Samuel Miles moved west toward the attacking British. This left the Jamacia Pass without any defenders. Learning that the pass was not defended anymore, Miles was ordered back. He arrived just in time to spot the tail end of Howe's column of baggage trains moving through the pass. Realizing the dangerous situation, Miles sent half of his men (250 troops) toward the main line to warn them and escape. With the other 250 troops, Miles attacked the baggage train. Almost all of them were captured, including Miles.
At 8:30 A.M., the British turning column reached Bedford. They had managed to march completely undetected behind Putnam's line.
At 9:00 A.M., Howe fired a pair of signal guns to alert Grant and von Heister to attack the front of the heights while Howe advanced against the rear. Unfortunately for Howe, only von Heister made their attack. He moved north up the main road in the middle of the battlefield. He ran into Sullivan's troops and attacked them. Within a few minutes, the Patriot line unraveled as the troops fled to the main Brooklyn line. Sullivan organized many of his men and made a defensive stand at Baker's Tavern. They were soon captured by von Heister's Hessians.
By 11:30 A.M., Alexander's troops were overwhelmed by Grant superior numbers. Grant had moved forward in a decisive attack that broke apart the Patriot line. Most of the Patriots tried to escape and fled toward Gowanus Creek. When Alexander learned that Cornwallis was blocking his retreat, Alexander launched a series of counterattacks with about 250 Maryland troops, commanded by Maj. Mordecai Gist. Unable to clear a large enough path, most of the Patriots, including Alexander, was captured.
After sweeping Putnam's troops off the Brooklyn Heights high ground, Howe's senior commanders wanted to continue their advance and attack the last line of Patriot defenses. Instead, Howe halted his troops, reorganized his command, and ordered entrenchments dug facing the Patriot defensive works. With control of the East River, he believed that Washington was trapped and had nowhere to go.
On August 28, severe rain storms prevented any fighting between Washington and Howe. Both sides stayed in place. Also, because of the high winds, Howe was unable to move his warships behind Washington's position.
On August 29, during the evening, Washington called a council-of-war to consult on the proper measures to be taken. It was determined that moving across the river was the only way to escape. Washington ordered that all boats that could be found to be gathered up. The plan was to use the boats to ferry his troops across the river to safety. This way, they could escape the British trap and withdraw undetected from Brooklyn Heights. A heavy rain and fog kept the patriot escape from being seen from Howe. Heavy winds continued to keep the British ships from advancing to Washington's position.
The withdrawal started soon after it was dark from two points, the upper and lower ferries, on the East River. The intention of evacuating the island had been so prudently concealed from the troops that they did not know where they were going. The field artillery, tents, baggage, and about 9,000 men were conveyed over East River, more than a mile wide, in less than 13 hours. Being only 600 yards away, Howe and the British army had no knowledge of the Patriot withdrawal that was proceeding.
On August 30, around 6:00 A.M., the last of the Patriots left the shore of Long island. The withdrawal had worked without the british finding out.
At 11:00 A.M., the heavy winds finally died down enough for the British warships to begin to move upriver.
At 11:30 A.M., the fog lifted. Howe ordered his troops to advance and take the Patriot works. When they arrived, they discovered that the Patriots were nowhere to be seen. Howe realized that he had let Washington and the Patriots slip through his grasp. The British warships were finally able to move upriver, just a few hours too late to stop the Patriots. If Howe could have captured Washington and his troops, this would have effectively ended the war.
Western Long Island
On September 11, 1776, the British received a delegation of Americans consisting of Benjamin Franklin, Edward Rutledge, and John Adams at the Conference House on the southwestern tip of Staten Island (known today as Tottenville) on the former estate of loyalist Christopher Billop. The peace conference failed as the Americans refused to revoke the Declaration of Independence. The terms were formally rejected on September 15.
On September 15, after heavily bombarding green militia forces, the British crossed to Manhattan, landing at Kip's Bay, and routed the Americans there as well. The following day, the two armies fought the Battle of Harlem Heights, resulting in a tactical draw. After a further battle at White Plains, Washington retreated across the Hudson to New Jersey. The British occupied New York until 1783, when they evacuated the city as agreed in the Treaty of Paris,.
On September 21, a fire broke out on Whitehall Street (widely believed to be at the Fighting Cocks Tavern) near the Battery in New York City. High winds carried it to nearly a quarter of the city's buildings, consuming between 300 and 600 buildings. The British accused the rebels of setting the fire, although native New Yorkers instead blamed the British.
In the wake of the fire, Nathan Hale, a captain in the Connecticut Rangers, volunteered to enter New York in civilian clothes. Posing as a Dutch schoolteacher, Hale successfully gathered intelligence but was captured before he could return to the rebel lines. Hale was captured on September 21, 1776, and hanged the next day on the orders of Howe. According to legend, Hale uttered before being hanged, "I only regret that I have but one life to lose for my country".
Eastern Long Island
While most of the battle was concentrated in western Long Island, within about 10 miles of Manhattan, British troops were also deployed to the east to capture the entire 110 mile length of Long Island to Montauk. The British met little or no opposition in this operation.
Henry B. Livingston was dispatched with 200 Continental troops to draw a line at what is now Shinnecock Canal at Hampton Bays to prevent the port of Sag Harbor from falling. Livingston, faced with insufficient manpower, abandoned Long Island to the British in September.
Residents of eastern Long Island were told to take a loyalty oath to the British government. In Sag Harbor, families met on September 14, 1776, to discuss the matter at the Sag Harbor Meeting House; 14 of the 35 families decided to evacuate to Connecticut.
The British planned to use Long Island as a staging ground for a new invasion of New England. They attempted to regulate ships going into Long Island Sound and blockaded Connecticut.
The exact number of American soldiers who fought in the battle is unknown, but estimates are that there were at least 10,000, mostly New York militia reinforced from Connecticut, Delaware, and Maryland. Perhaps 1,407 Americans were wounded, captured, or missing, while 312 were killed. A British report claimed the capture of 89 American officers, including Colonel Samuel Miles, and 1,097 others.
Out of 32,000 British and Germans (including 9,000 Hessians) on Long Island, they sustained a total loss of 377. Five British officers and 58 men were killed, while 13 officers and 275 men were wounded or went missing. Of the Hessian forces under Carl von Donop, two were killed, and three officers and 23 men were wounded.