After fighting broke out between British soldiers and American rebels in the spring of 1775, it took no time for both sides to realize the Hudson Valley would play a crucial role in the conflict. Three weeks later, the Continental Congress gathered in Philadelphia to organize a joint protest against British policies. The delegates immediately understood the need to build forts in the region. Later that summer, war planners in London similarly instructed their commanders to seize the Hudson and “cut off all communication by water” between the rebellious New England colonies and the rest of the continent, in order to bring the uprising to its knees.
For the British, seizing and securing the Hudson would require capturing the high promontories and hidden passes of the Highlands, which could be used to rain cannonballs down at enemy ships daring to pass through the narrow, windy gorge between the mountains. For the rebels, fortifying the Highlands would become a major logistics and engineering challenge that occupied the attention of military commanders like George Washington throughout the war.
On June 2, 1775, James Clinton and Christopher Tappen, two leaders of the rebellion in New York City, commissioned a sloop to take them upriver so they could scout the best locations for building forts along the Hudson. They quickly found the ideal spot: the narrowest part of the river, where a high cliff on the western bank and a large, elevated island to the east pinch the mighty stream into a sharp turn. The difficulty of navigating this notoriously turbulent stretch had led sailors to call it “World’s End.”

Construction first began on the island. A Dutch botanist named Bernard Romans was hired to oversee the building of a “grand bastion” to be named Fort Constitution—not after the United States Constitution, drawn up 12 years later, but the ancient, unwritten British constitution, which the rebels saw themselves as struggling to defend against imperial overreach.
Work went slowly, and Romans found himself at odds with the rebels who had hired him. They pointed out that Fort Constitution could easily be overpowered if the British managed to land a cannon on the high cliff on the other bank of the river—the West Point, as it now began to be called. Instead of continuing the project of building twin fortresses on each side of this strategic location, the Americans fired Romans and decided instead to build forts a few miles to the south, at the narrow, scenic point where Popolopen Creek enters the Hudson (the Bear Mountain Bridge stands there today). Two years later, in 1777, when the British finally sent a fleet of ships up the Hudson and those two forts were easily taken, the Americans would wish they had stuck with their initial plans.
Every few months, “Backstory” will follow along as the U.S. marks the 250th anniversary of the American Revolution—and the crucial events that happened here in the Hudson Valley.
Related: The Borscht Belt Historical Marker Project Honors Catskills History