Caleb Brewster: Revolutionary War hero

Written by Petty Officer 3rd Alissa Flockerzi

The whaleboat glided quietly and effortlessly through the calm water, concealed by the dark night sky. A shadow loomed over the rowboat as the men prepared to overtake the massive shipping vessel. Manned by a crew of no more than 15, Caleb Brewster and his sailors brought down one British ship at a time during the Revolutionary War, their victorious triumphs echoing through the ages. In the fight for American independence, each battle belonged to Gen. George Washington and paved the way for future citizens of the United States of America.

Descendant of Mayflower passenger William Brewster, Caleb Brewster was born in 1747 at Setauket, New York, and had sailed on a whaler to Greenland and on a merchant ship to London before the Revolutionary War. Upon his return to America in 1776, he accepted a commission as an ensign in the 4th New York Regiment. He was appointed as a first lieutenant in the 2nd Continental Artillery in January 1777 and then to captain lieutenant from June 1780 to 1783. He fought in many raids, including the Battle of Setauket and helped capture Fort St. George at Mastic under Maj. Benjamin Tallmadge’s command.

Brewster is highly recognized for his brave and daring contributions to The Culper Spy Ring, which was essentially the beginning of the Secret Service we know today.

In 1778, Tallmadge was appointed head of the spy ring at the request of Washington who tasked him to establish a trustworthy espionage network against the British in New York City. Tallmadge chose close friends, such as Brewster and Abraham Woodhull, and neighbors from Setauket who proved to be so discreet that their identities were kept secret until the 20th century. Tallmadge began relying on a variety of individuals instead of a solo person, establishing a new model of espionage. Together, they were able to aid the war effort from 1779 to 1783 by supplying information on British activity.

A sign honoring Caleb Brewster's contributions stands at the site of his home. U.S. Coast Guard photo by PA3 Alissa Flockerzi.

A sign honoring Caleb Brewster’s contributions stands at the site of his home. U.S. Coast Guard photo by Petty Officer 3rd Class Alissa Flockerzi.

With the help of Robert Townsend of Oyster Bay, who collected information in New York, which was brought to Setauket on horseback by Austin Roe, the Setauket tavern keeper, Woodhull prepared messages to Washington and Tallmadge informing them of the number, disposition and movement of the British forces. The intelligence provided to Washington and his troops was vital. Brewster was the link between Connecticut and Long Island, moving across the Sound in his whaleboats at least once a week. A woman named Nancy Strong was aware of Brewster’s secret landing areas and would hang out a black petticoat and one to six handkerchiefs on her clothesline denoting the number associated with the landing place where Tallmadge would meet Brewster.

The Westchester, a hotbed of Tories, and the British-occupied Hudson River seemed impossible to pass through when carrying such valuable secrets. Brewster’s knowledge of the local waters allowed him to use a variety of well-hidden coves near Strong’s Neck and Setauket Harbor while escaping detection from the British soldiers occupying the town. His knowledge of Long Island Sound shoreline made him an ideal choice for the spy ring.

The sound was an incredibly dangerous place of constant fighting and guerrilla warfare during the Revolution. He could navigate the waters to attack a ship much larger than his small rowboat or he could avoid detection and attack from other parties. He made several trips, attacking British shipping vessels and carrying messages back to Tallmadge to deliver to Washington. He was in every raiding party that ever took place on Long Island. He was described as a man large in stature, possessing a keen wit and an unrivaled sense of humor.

After the war, Brewster married Anne Lewis, the daughter of the Fairfield, Conn., wharf owner where he ran most of his wartime operations. He worked as a farmer and blacksmith before serving as a captain to the government ship in charge of preventing smuggling. This ship, known as a revenue cutter, was part of the predecessor to the United States Coast Guard.

Brewster began serving as an officer in the Revenue Cutter Service in 1797, about the time the Quasi-War with France began. By 1801, he received his captain’s commission and began serving as skipper of cutter Active, out of New York. He remained in the service until a year after the end of the War of 1812.

All of cutter Active’s missions during the War of 1812 were carried out under his command. During the war, Active excelled at providing the best maritime intelligence to authorities in New York and to Commodore Stephen Decatur, whose warships were trapped by the Royal Navy up the Thames River.

Brewster remained with the service from 1793 to 1816, when he retired to his farm in Black Rock, Conn. He died there in 1827, widely known as an outstanding patriot and a hero.

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  • IS1 Sean Killian

    Any excellent part of forgotten history. A great tie into the historical television series “Turn” that is on AMC.