Ever since the combined British and Hessian armies had arrived in New York harbor, the Americans had been watching, waiting, and wondering: when and where would the enemy attack? Those questions were finally answered on Long Island on August 27, 1776. Hundreds of Americans were captured, killed, or wounded; the rest were forced to retreat for their lives, and it looked as though the enemy might finish them off any day. Only a miracle could save them.
Before the battle, the Americans held the northern part of the island. A line of wooded hills known as the Heights of Gowan formed a natural barrier between them and their enemies. There were only a few roads through the hills, and the Americans guarded these closely (except the one farthest to the east, which was called the Jamaica Road — and leaving that one unguarded turned out to be a huge mistake). At the western end of the island, around Brooklyn Heights, they had built some fortifications which they could retreat to in case their outer defenses were overrun.
The British and Hessians were camped to the south of the hills. Their forces were far stronger than the Americans’, and they were confident that they would win. But then they discovered something that made things even easier for them: the Jamaica Road was virtually unguarded. If they could secretly take part of their army though the hills by that road, then they would have the Americans surrounded.
During the night of the 26th, Generals Clinton and Howe led part of the British army eastward to the Jamaica Road and then northward through the pass in the hills. There were five American officers on horseback patrolling the pass, but the British captured them by surprise, so the American army still didn’t know they were being surrounded.
In the early morning, the British and Hessians to the south of the hills began attacking the Americans. But they weren’t really trying to beat them yet: they just wanted to keep them distracted until everything was ready for the big attack.
When the British troops on the north fired some cannons as a signal that they were ready, the attack began in earnest from both sides. Badly outnumbered and totally outmaneuvered, the Americans were soon retreating: indeed, many of them were running for their lives, in sheer panic. Michael Graham, a 41-year-old Pennsylvania soldier, wrote:
It is impossible for me to describe the confusion and horror of the scene that ensued: the artillery flying with the chains over the horses’ backs, our men running in almost every direction, and run which way they would, they were almost sure to meet the British or Hessians. And the enemy huzzahing when they took prisoners made it truly a day of distress to the Americans. I escaped by getting behind the British that had been engaged with Lord Stirling and entered a swamp or marsh through which a great many of our men were retreating. Some of them were mired and crying to their fellows for God’s sake to help them out; but every man was intent on his own safety and no assistance was rendered. At the side of the marsh there was a pond which I took to be a millpond. Numbers, as they came to this pond, jumped in, and some were drowned. Soon after I entered the marsh, a cannonading commenced from our batteries on the British, and they retreated, and I got safely into camp. Out of the eight men that were taken from the company to which I belonged the day before the battle on guard, I only escaped. The others were either killed or taken prisoners.
Some of the Americans fought on; for example, the American general Lord Stirling led a couple hundred Marylanders in desperate attacks against overwhelming odds in order to gain time for the rest of his troops to escape to the fortifications at Brooklyn. It worked to some extent, but those Marylanders were practically wiped out, and Stirling was captured.
When the British troops charged toward Brooklyn, they were ready to storm the American fortifications immediately and destroy or capture the American army on the spot. But General Howe stopped them: he decided it would be easier to simply start digging trenches that would allow them to approach the American lines in safety. This would take longer, but it wouldn’t result in as many British and Hessian casualties — and the Americans weren’t going anywhere. This decision turned out to be a big mistake for General Howe and a tremendous blessing to the Americans.
Heavy rain set in. For two days and nights it rained. The Americans stood in the mud within their fortifications, anxiously waiting for the enemy to attack. They were exhausted from lack of sleep and wet to the skin, and much of their ammunition was soaked and useless. The British toiled on, night and day, digging trenches and drawing steadily closer to the American lines.
And then, on the night of August 29th, the Americans simply vanished.