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.