If you look at a modern map of the Battle of Long Island, the first thing you notice isn't the troop movements or the fancy red-and-blue lines. It’s the terrain. Specifically, the "Heights of Guan." To a tourist today, these are just the hilly bits of Prospect Park or Greenwood Cemetery. But in August 1776, those hills were a death trap. George Washington was a brilliant leader, but he wasn't exactly a master of Brooklyn's backroads. He leaned on a map that missed a single, vital opening: the Jamaica Pass. That one gap changed everything.
It was the first major battle after the Declaration of Independence. The stakes were basically "win or die." The British, led by General William Howe, had just been kicked out of Boston and they were coming for New York with the largest expeditionary force the 18th century had ever seen. Washington had his guys dug in along the coast and the ridges. He thought he had the high ground. He was wrong.
Why the Topography of Brooklyn Was a Nightmare
Brooklyn wasn't just a borough back then. It was a collection of small Dutch farming villages—Gowanus, Flatbush, Bedford—separated by a massive glacial ridge. This ridge acted like a natural wall. If you wanted to get from the coast to the American camps at Brooklyn Heights, you had to go through one of four "passes."
Think of these passes like narrow hallways in a house. The Americans guarded three of them: Martense Lane, Flatbush Pass, and Bedford Pass. They felt pretty good about it. But there was a fourth hallway way out to the east. The Jamaica Pass.
Washington’s map of the Battle of Long Island—at least the one in his head and the ones provided by his scouts—didn't account for the fact that the Jamaica Pass was almost totally undefended. Only five young officers on horseback were out there. They were captured within minutes. By the time the sun came up on August 27, the British weren't in front of the Americans; they were behind them.
It was a total mess. Imagine being a Continental soldier in the woods near what is now the Brooklyn Botanic Garden. You’re firing at Hessians (German mercenaries) in front of you, feeling okay, and then you hear bagpipes and drums coming from the forest behind you. That’s not a good day.
📖 Related: Ladies Cargo Khaki Pants: Why This 90s Throwback is Suddenly Everywhere Again
The "V" Shape That Defined the Conflict
When historians draw a map of the Battle of Long Island, they often use a "V" shape to illustrate the British flanking maneuver. While the Americans were distracted by a "feint" (a fake attack) at the Gowanus Road, the main British body—about 10,000 men—was swinging around the side.
Actually, "swinging around" is an understatement. They marched all night in total silence. No talking. No smoking. Just the sound of boots on dirt.
The Disaster at the Old Stone House
One of the most intense spots on any historical map is the Vechte-Cortelyou House, now known as the Old Stone House. This is where the "Maryland 400" made their famous stand.
While the rest of the American army was retreating (read: running for their lives) toward the forts on Brooklyn Heights, these Marylanders stayed behind. They charged a British position held by Lord Cornwallis. Not once. Not twice. They charged six times. They were outnumbered maybe ten to one. Most of them died right there in the marshes of Gowanus. But they bought Washington the time he needed to get the rest of his troops behind the inner fortifications.
Without that specific local geography—the marshy creek and that sturdy stone house—the Revolution might have ended right then and there.
Reading the Map: Where the Bodies Are Buried
If you’re trying to find these spots today, it’s kinda weird. You’re walking over hallowed ground while looking for a Chipotle.
🔗 Read more: Peace in a box: Why We are All Obsessed With Small Space Serenity
- Battle Hill: This is inside Greenwood Cemetery. It’s the highest point in Brooklyn. If you stand there today, you can see the Statue of Liberty. In 1776, you would have seen the British HMS Asia firing its cannons.
- The Marylanders’ Grave: There’s a nondescript lot on 3rd Avenue where many of those 400 soldiers are believed to be buried under the asphalt. It’s a sobering thought when you’re stuck in traffic.
- The Jamaica Pass: This is near the intersection of Broadway and Jamaica Avenue. Back then, it was just a lonely road through the woods. Today, it’s a chaotic intersection under an elevated train.
The Great Escape: A Map of the East River
The most miraculous part of the map of the Battle of Long Island isn't even the battle. It’s the retreat. After the beating they took on the 27th, the Americans were pinned against the East River. The British were preparing a siege. If the wind had stayed favorable for the British ships, they could have sailed into the river and cut off any escape. Washington would have been captured.
But the wind changed. Then a thick "providential" fog rolled in.
On the night of August 29, Washington gathered every boat he could find. Flatboats, rowboats, fishing smacks. He had a regiment of "Marbleheaders"—sailors and fishermen from Massachusetts—row 9,000 men across the river to Manhattan in total silence. They even wrapped their oars in rags to muffle the sound.
When the fog finally lifted the next morning, the British walked up to the American trenches and found... nothing. Just a few abandoned campfires. Washington was the last man on the last boat.
💡 You might also like: Finding the Right Happy Birthday Images for Mom From Daughter Without Looking Generic
Tactical Lessons from the Brooklyn Terrain
Military academies still look at this map because it’s a textbook example of how not to defend a position. Washington made several mistakes that any modern lieutenant would catch:
- Split Forces: He divided his army between Manhattan and Long Island, making it easy for the British navy to isolate them.
- Poor Intelligence: He relied on local militia who didn't properly scout the Jamaica Pass.
- Static Defense: He waited for the British to come to him rather than using the hills to his advantage for a mobile defense.
However, he also showed his greatest strength: knowing when to fold. The retreat was a masterpiece of logistics. It proved that the Americans didn't have to win every battle; they just had to not lose the entire army.
How to Explore the Map Yourself
If you actually want to see this history, don't just look at a screen. Get on the ground. The geography still tells the story.
1. Start at Battle Hill in Greenwood Cemetery. Look toward the harbor. You’ll see exactly why the British chose to land at Gravesend Bay. The view is unobstructed.
2. Walk the Gowanus Canal. It’s gross now, sure, but imagine it as a massive, muddy tidal marsh. That was the obstacle the Americans had to swim across to escape the British bayonets. Many drowned because their wool coats got waterlogged.
3. Visit the Old Stone House in J.J. Byrne Playground. They have a great diorama that explains the troop movements better than any 2D map.
4. Find the "Dongan Oak" Marker. It’s in Prospect Park. The Americans cut down a massive white oak tree to block the Flatbush Pass. The British eventually just walked around it, but the marker is still there.
The map of the Battle of Long Island is basically a map of a massive "oops" moment followed by a "holy crap, we're alive" moment. It’s the story of how the United States almost died in its crib because of a gap in the woods and some bad scouting.
If you’re researching this for a project or just because you’re a history nerd, focus on the "Lines of Defense" vs. the "Line of March." The gap between them is where the real story lives. You can find high-resolution digital scans of the 1776 Bernard Ratzer maps through the New York Public Library’s digital collection; they are the gold standard for seeing what the roads actually looked like before the grid system took over.
To truly understand the tactical layout, your next move should be to compare a 1776 topographical survey with a modern 3D terrain map of Brooklyn. Seeing the elevation changes in Prospect Park today makes it immediately obvious why the Jamaica Pass was such a glaring vulnerability. Check out the digital archives at the Museum of the American Revolution for the most accurate overlays of troop positions on modern street grids.