HistoricSiteMarkers
American Revolution

Site of the Dongan Oak

New York, Kings County, New York

Marker Inscription

At the Battle of Long Island, on the hill to the north of this site, the Americans had a redoubt with two guns, to guard the Old Valley Grove Road, called by the early settlers the "Porte", meaning gate-way through the hills, and which ran in front of...

The Story

This spot in what is now Prospect Park marks ground contested during the Battle of Long Island in August 1776, the first major engagement after the Declaration of Independence. American troops held a redoubt with two cannon on the rise nearby, guarding a pass through the hills — the old "gate-way" road the early Dutch settlers had used. To slow the advancing British, patriots felled the great Dongan Oak that stood at the gap, blocking the road.

Why it matters

The Battle of Long Island was the largest battle of the Revolution and nearly destroyed Washington's army, making his daring nighttime escape across the East River one of the war's turning points.

The story behind this marker

AI context

The era

In the summer of 1776, the ground that is now Prospect Park was rolling countryside on the western end of Long Island — a patchwork of Dutch farms, woodlots, and hills laced with old roads. The independence of the American colonies had just been declared that July, and everyone knew the British would answer with force.

The hills here were not just scenery; they were a barrier. A wooded ridge ran across the approach to the vital port at the mouth of the East River, and the roads that pierced it were the gateways an army would have to use. The early Dutch settlers had long understood this, giving one such gap a name that meant, simply, the "gate" through the hills.

When a massive British and Hessian force gathered in the harbor that August — the largest expedition the crown had yet sent across the ocean — those passes suddenly became the most important real estate in America. Whoever held the gates held the road to the city.

People & events

The marker sets the scene at the Battle of Long Island, fought on August 27, 1776. On the rise just to the north, American troops had thrown up a redoubt — a small earthwork fort — and mounted two cannon to command the old road through the pass, the "gate-way" the settlers had used for generations.

As the British pressed forward, the defenders reached for a desperate, practical measure. A great oak tree stood at the gap, and patriots felled it across the road to slow the advancing column — turning a living landmark into a barricade. The tree gave this ground its name, and its fall marks one of the small, human moments inside an enormous battle.

The stand at the pass was fierce but could not hold. The British had found a way around the American positions, and the day turned into a punishing defeat. Yet the details preserved here — the two guns, the earthwork, the barricaded gate — let you stand inside the fight at the scale of the men who actually fought it.

Its place in the American story

The Battle of Long Island was the largest battle of the entire Revolutionary War, and it went badly for the Americans. Washington's young army was outflanked and driven back, and for a moment it looked as though the rebellion might be crushed in its infancy, only weeks after independence had been declared.

What saved it was not victory but escape. Cornered against the East River with the enemy in front of him, Washington pulled his battered army across the water to Manhattan in a single desperate night, under cover of darkness and fog. The retreat kept the Continental Army — and the cause — alive to fight another day.

That is why a felled tree and a two-gun redoubt matter far beyond Brooklyn. This ground is where the war's largest battle was lost and where, through a narrow escape, the possibility of eventual American victory was preserved. The whole long struggle for independence turned, in part, on what happened at passes like this one.

If you visit

You'll be walking a battlefield hidden inside a beloved city park. Prospect Park today is lawns, ballfields, and shade trees, but the terrain itself is the artifact — those gentle rises and wooded slopes are the very hills that made this ground worth fighting over. Read the land, and the tactics start to make sense.

Look for the pass. The old gateway through the hills is still a recognizable feature of the park's landscape, and standing in the gap you can imagine why a single oak dropped across the road could buy defenders precious minutes.

This is an easy and rewarding stop on any tour of Revolutionary New York. Pair it with the harbor and the East River waterfront, picture the nighttime evacuation across that water, and a stroll in the park becomes a walk through one of the war's decisive days.

Written by AI to add context, grounded in the marker’s inscription and the historical record. The inscription above is the original, unaltered text.

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  • · Battle of Long Island

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American RevolutionMonument

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