In January 1776, George Washington appointed General Charles Lee to oversee the construction of defenses in New York, providing instructions that noted “you are to put that City in the best posture of Defence which the Season and Circumstances will admit of.” Lee recognized that the geography of New York, including its commodious harbor and rivers, greatly favored the British. Seeing this, he devised a strategy that hinged on ways to make New York “a most advantageous field of battle,” and make it as costly as possible for the British to take.
The American retreat across Gowanus Creek, from a painting by Alonzo Chappel. At the time, the tidal creek, surrounded by marshland, went nearly as far as Flatbush Avenue. From History of the United States, from the earliest period to the administration of President Johnson, Volume 1 by J.A. Spencer.
Fort George and The Battery, commanding the harbor at the tip of Manhattan, were strengthened, and a larger battery, the Bayard’s Hill Redoubt, was built on the tallest point in lower Manhattan; it was also referred to as the “Independent Battery” or by the nickname “Bunker Hill.” A new fortification was built on Governor’s Island, guarding the approach to the East River. When Lee later left for Charleston, the responsibility passed to General Nathanael Greene.
Fort George and the Independent Battery atop Bayard’s Mount. From Pictorial Field Book of the Revolution, Vol II by Benson John Lossing.
In northern Manhattan Fort Washington and Fort Cox were built along with several redoubts and defensive lines. A battery was also constructed at Horn’s Hook overlooking Hell Gate. Smaller fortifications were erected to protect the forts, and one of these batteries may have later been used as the foundation for as a blockhouse built during the War of 1812 (which is currently located in Central Park and known as Blockhouse 1).
The Blockhouse in Central Park. It still stands today in the northern section of the park. From The Annual Report of the American Scenic and Historic Preservation Society to the Legislature of the State of New York, 1911.
Since the high ground of Brooklyn overlooked Manhattan and the East River, it was an important location to defend. Charles Lee wrote to Washington with a plan to prepare “a Post or retrenched encampment on Long Island opposite to the City for three thousand men.” A string of forts and associated defensive structures was built to protect the heights. These included Fort Putnam, Fort Greene and the Oblong redoubt, a small redoubt on the old Ponkiesbergh, and Fort Box, which were all connected by trenches. The low-lying land aside the heights, with the Gowanus Creek on one side, and the Wallabout mud flats on the other, served as an additional defensive measure, as it created a natural bottleneck for anyone daring to attack it. By May, the lines at the heights were being continuously manned.
The redoubt on Ponkiesbergh, also known as the Cobble Hill Fort.
Freeke’s Millpond and Fort Box. A mill had been on the site since the 1660s, but the mills along the creek were set on fire during the battle. From Battle of Long Island: With connected Preceding Events, and the Subsequent American Retreat by T.W. Field.
These heights are part of a terminal moraine that was formed at the edge of the Wisconsin ice sheet, pushing massive amounts of rock debris forward, which created the hills that run in a diagonal direction across Staten Island, Brooklyn, Queens, and Long Island. The glacier and its melting water carved out passes between the hills, which were thickly wooded and provided a strong place for the Americans.
A sketch showing the approximate direction of the Wisconsin ice sheet and the position of the terminal moraine. Geology of New York City and Vicinity by Chester A. Reeds.
An additional fort was also built in Red Hook, which was proudly called Fort Defiance. The forward lines were along the Heights of Guan (now known as the Harbor Hill Moraine). Of the passes, four were key to the defense of Brooklyn: the Martense Pass (closest to the Narrows), the Flatbush Pass, the Bedford Pass, and the Jamaica Pass. It would be the Martense and Flatbush Passes that would be most heavily defended.
The British fleet had sailed from Halifax and in late June they began arriving off of Sandy Hook. General William Howe sent a party ashore near Gravesend to see if it would be suitable to land there, but a small group of Americans opposed them, and the decision was made to land on Staten Island, which was also a major Loyalist stronghold. Admiral Richard Howe arrived by mid-July, followed by the remnants of the fleet that were rebuffed at Charleston, and then a large contingent of Hessians.
The American defenses were tested by the British, who sent the warships Phoenix and Rose up the Hudson. The guns from Governors Island, Fort Defiance, and The Battery all fired upon the ships, although any damage was superficial. The return fire struck some residences, but the only casualties were some inexperienced cannoneers who accidentally blew themselves up. City residents were greatly unnerved by this, with one woman writing that she “never underwent such a fright in all my life.” With a battle inevitably coming, many New Yorkers fled the city.
By mid-August, over 400 vessels were anchored off of Staten Island, with an estimated 32,000 soldiers gathering there. On August 22nd, the British crossed the Narrows, landing at Denyse’s Ferry, near what is now Fort Hamilton. Others landed in Gravesend Bay, bringing the total number of British and Hessian soldiers on Long Island to 20,000. Washington, who thought that the main focus of the British would be York Island (Manhattan), was wary that this was a feint, but sent troops across the East River.
Denyse’s Ferry. The house, owned by Denyse Denyse, took cannon fire from the British during their landing. From Historic and Antiquarian Scenes in Brooklyn and its Vicinity by T. W. Field.
Although the army numbered as many as 20,000, a great number of the men were badly sick, including some generals. Nathanael Greene was stricken with camp fever before the battle and replaced by Israel Putnam. Of the rest, with men still needed to defend Manhattan in case of an attack there, perhaps only 7,000 soldiers (some sources say as many as 11,000 were available) would be available to be ferried over to Brooklyn to face the British force there.
Skirmishing began on the 22nd, initially breaking out along the Shore Road that followed the water’s edge up to Gowanus. British warships fired upon the heights, and attempted to go up the East River but were repelled, although in the process one of the shots hit Fort Defiance directly, knocking it out of service. By the next day, the fighting was centered around Flatbush, where the Hessians had set up their camp. The Americans hauled cannons up to the hills and fired them on the Hessians, and picked them off from the woods.
Both sides engaged in reconnaissance and probed the camps and fortifications of their opponents. General Washington inspected the lines on the 24th, putting General Putnam in charge. Unfortunately for the Americans, General Putnam failed to place enough soldiers to guard the Jamaica Pass. General Henry Clinton, who grew up in New York, inspected the American lines in the next days, and received considerable intelligence passed on by area Loyalists. He came up with an ambitious plan to have soldiers march to the Jamaica Pass and flank the American left, and convinced General Howe of its merits.
On the evening of the 26th, Generals Clinton and Howe, along with General Charles Cornwallis, led 10,000 troops on a march along the King’s Highway from Flatlands to New Lots and onto the Jamaica Pass via Howard’s Tavern. They left fires burning in their camps as the soldiers snuck away, with an advanced party to saw down any trees, and scouts to alert them of any potential American movements.
By 3 AM on the 27th, the flanking column reached Howard’s Tavern, and the generals took the proprietor and his son as prisoners, forcing the two to lead the British generals over the pass. To their surprise, they found the pass was only guarded by a small vedette, which was easily captured (General John Sullivan later claimed to have paid these five officers to guard the pass). The British and Hessians made room for their heavy cannon to be pulled up the hills, and filed past on their way to Bedford Village, where they were to gather and get what little rest they could before the battle began in earnest.
Howard’s Tavern, 1776. Also known as the Rising Sun Tavern, it stood at the corner of Broadway and Jamaica Avenue. From Historic and Antiquarian Scenes in Brooklyn and its Vicinity by T. W. Field.
Fighting broke out at the Red Lion Inn along the Shore Road late on the 26th, providing a convenient cover for the flanking march. An American regiment came across British soldiers foraging in a watermelon patch near the inn. Skirmishing throughout the night erupted into a full engagement by dawn. Washington thought the main British attack would come on the right of his lines, and the early morning din and a series of erroneous intelligence reports seemed to confirm this. The Americans didn’t realize that this attack was a feint, designed to allow time for the flanking march. General William Alexander “Lord” Stirling, with troops from New York, Connecticut, Pennsylvania, Delaware, and Maryland, moved to oppose General James Grant.
At the Flatbush Pass, General Sullivan was preparing for a strike by an overwhelming Hessian force when he heard the two signal cannons that alerted the British to launch their full attack. The troops defending the Bedford Pass had come across the rear of the British march and an attack upon it failed once the superior force was discovered behind the lines. These men fled towards the Flatbush Pass, and Sullivan, also realizing that the enemy was enveloping him, attempted to reposition his men. However, what was then his rear line fell apart after a ferocious bayonet charge from the Hessians broke through the defenses and overran the intrenchments, and his front quickly gave way. Sullivan ordered a retreat, but near Mount Prospect they were attacked again on two fronts and Sullivan was captured.
Battle Pass as it looked in 1776. Soldiers cut down the venerable Dongan Oak, which marked the border between Brooklyn and Flatbush, to curtail the British advance. The smaller of the hills had a small redoubt covering the pass. The taller one, Lookout Hill, is where the fabled 400 Marylanders under Lord Stirling began their cover of the American retreat. From Historic and Antiquarian Scenes in Brooklyn and its Vicinity by T. W. Field.
Battle Pass, in what was by then Prospect Park, 1866 (top); Photo of Battle Pass in 1892 (bottom). From The Eagle and Brooklyn, the record of the progress of the Brooklyn Daily Eagle, edited by Henry W.B. Howard.
With most of the American lines collapsing by mid-morning, the last resistance fell to Lord Stirling and his men, who had already been fighting for several hours. He stretched his line from a sandy hill called Blockje’s Bergh over to the heights commanding the road to Gowanus (in what is now Greenwood Cemetery), and this ground was hotly contested. Although at one point the British had nearly run out of ammunition, they were resupplied and reinforced by an additional 4,000 troops.
The statue of Minerva on the Altar to Liberty erected atop Battle Hill in what is now Greenwood Cemetery in 1919. This gives an excellent view of the vantage point from the tallest point in Brooklyn. From Dedication of monument and altar to Liberty on Battle Hill in Greenwood Cemetery by the Kings County Historical Society.
Following the capture of the Flatbush Pass, more British and Hessians were pouring in from the west and cutting off Stirling’s rear. He realized that there was only a slim chance for his men to escape, and he ordered a retreat across the swampy Gowanus Creek. He then took a contingent of Marylanders and led a series of daring attacks near the Old Stone (Vechte-Cortelyou) house. The sacrifice of the immortalized “Maryland 400” allowed many of the other men to escape to safety.
The Vechte-Cortelyou House. Built in 1699 by Claes Vechte, it was later owned by the Cortelyou family. It remained standing after the battle, and was a popular tourist site, even serving as a clubhouse for the Brooklyn Base Ball Club. The house was destroyed by fire in 1897 and the land came close to being heavily developed until public outcry prompted the city to dig up what remained and reconstruct the house on a site nearby. From The stone house at Gowanus, scene of the battle of Long Island by Georgia Fraser.
The battle was over by noon, and the British were the clear victors. Any Americans that were able to retreat were behind the line of entrenchments protecting Brooklyn Heights. Estimates of the casualties vary widely, although there were at least 1,200 dead and 1,500 wounded, captured, or missing on the American side (this total is likely higher since meticulous records were not yet being kept), and 350-400 total casualties for the British and Hessians.
Washington had brought over reinforcements from New York but instead of attacking the forts, Howe had his men dig in for a siege. This proclivity would continue on throughout the war. The British dug a line of trenches parallel to the ones protecting Brooklyn Heights. Over the next day the soldiers peered at each other from across the no man’s land. Periodically men would rise up and shoot at each other, but there was no concerted effort for an attack on either side.
A map drawn by J.W. Ewing in September 1776, showing the British attack. He depicts the stand of the Maryland 400 (A) against the British, coming in force from the south and west (B), and the retreat across Gowanus Creek (L-P). He also shows how close the British camp (R) was to the American forts (G) and camp (C). From The Campaign of 1776 around New York and Brooklyn by Henry Phelps Johnston.
Fortunately for the Americans, the wind had prevented Admiral Howe from sailing up the East River and cutting off Brooklyn Heights completely. A storm blew in and pelted both sides, rendering much of their ammunition useless. Washington called a Council of War on the 29th and a near unanimous decision was made to withdraw from Long Island altogether. Colonel John Glover and men from Marblehead, Massachusetts, along with other mariners from the state, had come over, and Washington appointed them to assist in ferrying soldiers across the East River, leaving from a point that is now at the end of Fulton Street.
Colonel Glover directing Americans in the retreat from Brooklyn Heights. From The Boys of ‘76, A History of the Battles of the Revolution by Charles Carleton Coffin.
This was an immense logistical undertaking, and great care had to be taken in order to not alert the British of what was happening. Indeed, the utmost secrecy was maintained throughout the night, and those remaining on the front lines made it look like they were fully manned. A thick fog descended in the early hours, which helped cover the retreat, and by the morning all of the Americans had been evacuated from their positions, with George Washington leaving in one of the last boats. The British didn’t figure out what was happening until after sunrise, when the Americans were safe, at least temporarily, on Manhattan.
Select Sources
Under the Guns: New York, 1775-1776 by Bruce Bliven
Gotham: A History of New York City to 1898 (The History of New York Series) by Edwin G. Burrows and Mike Wallace
Battle of Brooklyn 1776 by John J. Gallagher
Divided Loyalties: How the American Revolution Came to New York by Richard M. Ketchum
The Maryland 400 in the Battle of Long Island, 1776 by Linda Davis Reno
The Battle for New York: The City at the Heart of the American Revolution by Barnet Schecter