The rebellious American colonies and the British Empire realized early in the Revolutionary War that control of the Hudson River Valley was the key to the success or failure of the fight for independence. In those years before superhighways, railroads and airplanes, waterways such as the Hudson were the great arteries of transportation for people and goods. New York was the linchpin between New England and the more southerly colonies, and the Hudson was the main street of New York.
Despite its meager population the Peekskill-Van Cortlandtville area became a focal point during the fight for freedom. Gen. George Washington established headquarters for the American Highland Command there for two years and maintained his own headquarters in Peekskill off and on for extended periods.
Washington considered this locale so important that it became a major assembly area for troops and militia as well as arms and supplies. The area was centrally located for movement of men and materiel up and down the river, east into New England or west and south via the King’s Ferry between nearby Verplanck and Stony Point.
One of Washington’s greatest fears was that the British would move troops up the river, seize control of the Hudson Valley and split the new nation in two. His fears were well founded. Since August 1776 British forces under the command of Gen. Sir William Howe had been pushing the Americans north from the New York City area – first from Long Island, then from Manhattan and into Westchester County, where the armies clashed at Pell’s Point and White Plains in October.
When winter released its icy grip on the Hudson River in early 1777 the British drive for mastery of New York and the Hudson Valley resumed when a fleet of more than a dozen ships and smaller craft under the command of Col. Bird sailed north from New York City on March 21. The British goal was Peekskill, which had been established by Washington the previous November as the command post and headquarters for the Hudson Valley. Fort Hill, rising north of present-day Main Street, and the surrounding area presented an inviting target with barracks, storehouses and mills. A short distance north lay the Continental Village supply depot.
Bird’s fleet appeared in Peekskill Bay around noon on Sunday, March 23. Within an hour 500 men landed at Lent’s Cove. After burning a house owned by the Lent family the British troops, accompanied by four light artillery pieces, marched up the Post Road and took up positions on Drum Hill, where they began firing at the settlement and the American positions on Fort Hill.
Brig. Gen. Alexander McDougall, in charge of the 250-member Highland Command, used advance knowledge of the British expedition to remove as much of his supplies as possible to nearby posts before the fleet arrived. Outnumbered 2-1, he quickly realized that a defense of Peekskill (then commonly known as Peekskill Landing) would be foolhardy. Carrying what additional supplies he could, he ordered the burning of what remained, along with the barracks, principal storehouses and a wharf, and retreated a couple of miles north to Gallows Hill to protect Continental Village.
As McDougall withdrew, the raiders continued the destruction he started. A British officer, while doubling the size of the American force and crediting his comrades with some of the work carried out by McDougall’s troops, provided the following account in the March 31, 1777, edition of William Gaine’s Mercury, published in New York: The 500-man British force landed without incident and the “almost unapprised” rebels, though “at least equal” in number, soon fled, first burning mills and supplies on Gregory’s Creek (McGregory Brook, near the present Zeph’s Restaurant on Central Avenue). The British then destroyed barracks, workshops and storehouses along with more than 150 wagons, tools, food, ammunition, uniforms, leather, bark for tanning and more than 400 hogsheads of rum. They took to their ships other materials for their own use. “The whole affair was carried on with the utmost spirit and harmony, and to the honor of the soldiers it may be said, that not one of them, among the streams of rum that run about in every quarter, was in the least disordered in his duty. … Nothing could exceed the cool intrepidity and precautions of the commanding officers throughout the enterprise, nor the alacrity and vigor of the whole party. Not a man was lost or hurt upon the occasion.”
Meanwhile, the American contingent at nearby Fort Independence (also known as Fort Constitution), under the command of Lt. Col. Marinus Willett, was preparing for its customary Sunday parade when orders arrived from McDougall to leave a small guard at the Hudson River outpost on Roa Hook and bring the rest of the force to Gallows Hill.
On Monday, March 24, 200 British troops marched up the Post Road (later known as Hillside Avenue and Oregon Road) to the Twin Hills, just south of the Van Cortlandt family’s Upper Manor House, where McDougall had posted an advance guard. Scouts informed him of the British advance but the general, as he explained in a letter to Washington, thought he had too few men to attack and risk a defeat that would expose the Highlands and the large Fishkill Supply Depot to a British invasion. In view of his responsibilities for the entire Highlands region, the general reasoned it was better to lose supplies and facilities, such as those at Peekskill, than to risk losing his army.
When Willett and his 80 men joined McDougall at the Gallows Hill barracks Monday afternoon the colonel observed a British detachment burning a house. He also observed that the detachment was separated from the rest of the troops by a ravine, and he implored McDougall to attack them. As the sun was setting Willett finally persuaded his cautious commander to let him do so. While other Americans created a diversion to the west, the zealous colonel ordered his 80 men to fix bayonets and attacked the eastern flank of the British. Willett’s troops overwhelmed the British with the unexpected assault, sniping at them from behind trees and stone walls. Aided by darkness the British fled back to Fort Hill. After waiting for the full moon to rise, the entire invasion force retreated to its ships and sailed back to New York the next day. McDougall returned to Peekskill and reoccupied the Fort Hill redoubts and the settlement.
Willett’s counterattack left nine British dead and four wounded. Four more British were killed while trying to burn American boats at Canopus Creek The colonel reported two men killed and four or five wounded.
Stung by Willett’s counterattack, the British did not return to the Hudson Highlands in force until the following October.