General George Washington, Governor George Clinton and Lord Stirling all knew about Anthony’s Nose. Not because it was part of someone’s anatomy, but because it was a prominent feature along the Hudson River, the highest place in Westchester County. Anthony’s Nose resembles a person’s nose when viewed in profile from the Hudson River, and so was a well known landmark.
Anthony’s Nose was also strategically important. The road at its base along the Hudson River (present day US 202) was a choke-point in the Hudson Highlands north of Peekskill. The only wagon road on the east side of the Hudson River, the Albany Post Road, ran from NYC to Albany, and passed along the river here. It could be easily defended from atop the steep rock face.
Henry Wisner (of Goshen) a delegate to the Continental Congress reported: “there is a hill to the north of Peekskill so situated, with a road winding along the side of it, that ten men on top, by rolling stones, could prevent as many thousand from passing…nothing more need be done than to keep great quantities of stones at different places where the troops must pass…”
During June-July 1776 hundreds of British ships assembled in the New York Harbor. They carried an estimated 15,000 British and Hessian troops who were threatening to attack Long Island and the city itself. At the time, General Washington had an estimated army of 10,000 in the city, mostly constructing fortifications and preparing for the inevitable attack. During early July British ships sailed up the Hudson into Haverstraw Bay, probing Patriot defenses and the ability of their fortifications to resist an assault up the Hudson River.
As word of these maneuvers traveled up the Hudson River Valley, news of the threat of a British invasion spread. If the British got control of the Hudson, communication between colonies would be blocked and the fight for independence would be over. Lord Stirling (General William Alexander), was the officer in charge of building fortifications that would stop British ships from passing through the Hudson Highlands. He inherited a battery on Constitution Island, in the river below Anthony’s Nose, which was well armed, but remained vulnerable to attack without fortifications on the high ground opposite Anthony’s Nose. Lord Stirling shifted construction efforts there.
During the Spring and Summer of 1776, Washington’s Army was totally committed to the defense of New York City and Long Island, so the job of stopping British ships from sailing beyond Anthony’s Nose largely fell to local militiamen, who already had their hands full with Loyalists. The Committee of Safety in Poughkeepsie appealed directly to neighboring patriot authorities for assistance. Officials in Litchfield County, Connecticut, quickly mustered 300 militiamen from the Sharon area and directed them to assist their neighbors. Men in Berkshire County Massachusetts were also alerted and 300 militiamen were mustered and ordered to march to defend the Hudson Highlands.
On the west side of the Hudson, General George Clinton (later Governor and Vice-President) mustered the Orange and Ulster County militia forces and were ordered to secure river landings and guard roads on the west side of the river. As the senior officer in the area, Clinton was put in charge of all militia forces in the Hudson Highlands on both sides of the river. Washington wrote to General Clinton at Fort Montgomery that the British intended to seize the passes in the Highlands. He ordered Clinton to secure these passes, particularly at the place where the Albany Post Road ran by Anthony’s Nose. Dutchess and Westchester militia reinforced and fortified the east side of the river.
The stage was set for a confrontation and Anthony’s Nose was prominently featured when it finally occurred on July 17, 1776.
During 1777 Washington ordered the construction of a large chain across the Hudson from the shore near Anthony’s Nose to the opposite shore below Fort Montgomery. Although meant to keep the British ships from passing, it didn’t work. The chain was sunk after several well placed British cannon shots. It was blown to bits and on October 6, 1777, the British sailed through the opening, destroyed Fort Constitution, attacked Forts Montgomery and Clinton and sailed up to Kingston and burned most of the city to the ground.
During 1778 it was ordered that the chain be restored under the direction of Count and Colonel Thaddeus Kosciusko. On March 28, 1779 it was still not completed, but on Nov 6, 1779 it was recorded that “it will soon be time to draw the chain (out of the river).”
During April 1780, the chain was again stretched across the river and taken out of the water on October 16 (after the defection of Benedict Arnold). On April 10, 1781 the chain was once more reinstalled across the river.
More detailed information about the participation of the militiamen who guarded the Hudson Highlands during 1776 can be found in my book, Guarding Peekskill: The Berkshire Militia’s Role.