 relatively safe place and home to the Patriot cause. He was not alone in fleeing the British occupied Long Island. One in six Long Islanders departed to Connecticut as refugees in 1776. One of Brewster’s initial actions after moving to Connecticut, was to assist other patriot refugees to escape Long Island by using his boat to crisscross Long Island Sound, ferrying out the patriot sympathizers in clandestine operations. One of his passengers was a signer of the Declaration of Independence, William Floyd.
The Black Rock harbor was the point of attack for the patriot cause. The deep-water, historic shipbuilding seaport was a depository for privateers, British prisoners, and launching ground for schooners, sloops and whaleboats. Black Rock became a focal point for battles and espionage during the entire war period from 1776 to 1783, during which the British occupied New York City, part of Westchester and Long Island.
Brewster carried out a number of different missions during the war. He acted as intelligence gatherer, lieutenant in the artillery, spy letter courier, privateer, and army officer commanding a fleet of whaleboats against the British. By the spring of 1776, Brewster joined the Continental Army as Lieutenant. By 1778 he had fleet of three whaleboats. Brewster was under direct orders from George Washington through Benjamin Tallmadge, organizer and leader of the Revolutionary War’s Culper Spy Ring, which began in 1778 and operated on Long Island, New York City and Black Rock. Codes and aliases concealed the identities of the spy members. Brewster was the only spy to sign letters under his real name instead of his secret agent code 725.
The spy ring provided valuable information to General Washington at the height of the American Revolution. Having reliable intelligence of expected British troop movements was essential. George Washington was unable to setup a spy network prior to the 1776 battle in New York due to his hurried retreat from the British. Outwitting the enemy in surprise attacks would prove more effective against the much more powerful British navy. Therefore George Washington’s most valuable strategic weapon was not his military force, but rather intelligence and Brewster was at the center of the spy ring.
From the moment General Washington lost the battle in New York in 1776, he set Black Rock as one of the front lines of the war and counted on intelligence from Brewster. If you could not defeat the enemy by numbers of troops, you would have to do so with information and strategy.
Today, we know of a total of fourteen letters of correspondence between George Washington and Caleb Brewster, thirteen of which are in the Library of Congress. There are nine letters from Washington to Brewster, and five letters to the General from Brewster. The very first letter from Brewster has not yet been found. In his first letter to Caleb Brewster, writing from White Plains on August 8, 1778, General Washington sets the tone for the espionage needs. Washington requested the Black Rock patriot to “have a strict watch kept upon the Enemy’s Ships of War, and give me the earliest notice of their Sailing from the hook. To obtain speedy and certain intelligence of this matter may be of great Importance to the French Fleet.”
After this first correspondence with Washington, the Black Rock spy gathered intelligence on the British military movements and wrote Washington that “the Ships of war are Left the Harbours in and about Huntington—Genrl Tryon and Delancee have their Quarters at the Fly at the Head of Flushing Bay with about Seven Hundred Troops that Returnd with them from the East End of the Island.”
Caleb Brewster and the Culper Spy Ring achieved major milestones. For example, the spy ring prevented advance British knowledge of the French arrival in America to help the patriot cause. It was also through such intelligence gathering, that the patriots revealed the identity of American’s most famous of traitor, Benedict Arnold. Brewster’s intelligence missions would also successfully warn General Washington of the burning