Courageous Colonial Spy

Footnotes to Long Island History


MARCH 3,1969


Thomas R. Bayles

      Caleb Brewster of Setauket was an important member of the American spy ring that operated out of Setauket during the Revolutionary war under the direction of Major Tallmadge.

       Austin Roe Setauket brought the secret messages from the chief spy in New York, Robert Townsend (alias Culper, jr.). These were turned over to Abraham Woodhull, who in turn gave them to Caleb Brewster, who carried them across the sound in one of his boats and delivered them to Major Tallmadge, who delivered them to Gen. Washington wherever he might be located.

       Caleb Brewster was born in Setauket in 1747, a great grandson of the Rev. Nathaniel Brewster, the first minister of the old town church in Setauket. His father was a farmer and as was too often the case in that day gave his son only a limited education. Caleb was an active boy and was anxious to explore the world beyond his native village, so at the age of 19 went on a whaling ship bound for the coast of Greenland under command of Capt. Jonathan Worth.

       His next voyage was to London in a merchant ship, upon his return found his country engaged in the Revolutionary war. He immediately volunteered his service and within a short time was made a lieutenant of artillery. He was held in such high esteem by his officers and the commander in chief for his integrity courage and patriotism that in 1778 he was employed as a secret agent by Congress. Through the rest of the war he devoted himself in procuring and transmitting important information of the British Army in New York and on Long Island.

       Brewster was among those who under Col. Parsons crossed the sound of Long Island in 1777, for the purpose of capturing a company of British soldiers who had taken possession and made a fort of the Presbyterian church at Setauket. This expedition was not successful, as while they were making their attack on the British, in the old church, word came that reinforcements were coming down the sound to aid the British so the attack was abandoned.

       For several years, Brewster was the trusted messenger of the secret messages from Setauket to the headquarters of Major Tallmadge, across the sound and his lightly armed whaleboats with good men traveled this route as often as was necessary. He sailed under his own name and made no attempt to keep secret which side he served on. In addition to this he captured several supply ships headed for the British army in New York, and also led his men on raids across Long Island, burning and wrecking whatever they could find belonging to the British. He had many encounters with the enemy, and was sometimes wounded but always came off victorious and was never caught.

       He was with Major Tallmadge in November 1780 in the expedition that came across the sound from Fairfield Conn., and landed at MT. Sinai; then marched across the Island and made a successful attack on the British Fort St. George at Mastic. They returned the same day with their prisoners and part on the force went back by the way of Coram where they burned a hay stack of 300 tons collected there by the British.

       On December 7, 1782, Capt. Brewster with the whaleboats under his command gave chase to several armed boats of the enemy in the sound, and after a desperate fight succeeded in capturing two of them. During this encounter, his shoulder was pierced with a rifle ball and he was hospitalized for some time, after which he was placed on the pension roll of the army for the rest of his life. He was engaged in several other important encounters with the enemy on the water after this and in 1783 captured the "Fox" an armed British vessel in the sound during a short but fierce encounter.

       In 1784 he married Anne daughter of Jonathan Lewis of Fairfield, Conn., where he continued to live when not in public service. He was long remembered for his great size his fine proportions vigorous constitution unrivaled with and his devil may care bearing. He died on his farm at Black Rock, Conn., at the age of 79.

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