By Robert Foley
Caleb Brewster left the quiet life on his family farm home in Setauket, Long Island, at 19 years old for the adventure of a position on a Nantucket whaler. He then pursued a life at sea as a mate on a merchant ship. However, as soon as news of the American Revolution and of the shots of the Battle of Lexington and Concord reached his ship, he quickly returned home. It was war against British oppression.
It was May of 1775. He was 28 years old and the timing was perfect. The Continental Congress authorized our country’s first Navy soon after. Brewster’s skills in navigating whaleboats and merchant ships would prove essential in outmaneuvering British ships. His knowledge of the shoreline and his close relationships with other key patriot spies, his courage to enter enemy territory and retrieve spy letters, his whaleboat battles, were all noteworthy contributions to the patriot effort.
In December 1775, Brewster joined the Suffolk Country Minute Men, local self-trained colonists who independently organized militia companies known for being ready in a minute’s notice. They were among the first to fight in the American Revolution. Brewster was one of seventy Minute Men in that company. The patriots opposed the “intolerable acts” imposed upon by the British, which included immunity from prosecution. If British troops harmed local residents, they could avoid prosecution for criminal offence, which some at the time called the “murder act.”
Brewster’s hometown was soon under occupation. In 1776, when the British invaded New York City, Setauket, Long Island became a center for British commanders and would soon be under martial law. Residents could not travel to or from the city or bring any goods without a permit. Moreover, anyone who had signed a patriot document such as that of the Minute Men, stating the necessity of taking up arms against the British, was at great risk. Brewster fled to Black Rock, Connecticut, which was part of the town of Fairfield at the time. Brewster would find Connecticut to be a 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 mor