Monday, May 20, 2024
Historical Accounts, Maritime, Veterans and Wars

Caleb Brewster in the Revolutionary War

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 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 of Fairfield in 1779. Unfortunately, Washington was unable to respond in time because he was away inspecting the troops for several days.

Timing was essential for intelligence to be of any use. Delivery time was reduced to one week when Washington’s cavalry was stationed close by, in the Greenfield Hill section of Fairfield.  Having a mounted horseman ready to deliver messages that Brewster picked up from across Long Island shortened the total delivery time of spy letters picked up from New York. The new express delivery service utilized Washington’s cavalry, the 2nd Continental Light Dragoons, Sheldon’s Horse that had been commissioned by the Continental Congress on December 12, 1776 and named after Colonel Elisha Sheldon. The cavalry is still in existence today. The espionage ring provided messages and spy letters originating in New York, then carried 55 miles from Manhattan to Setauket by horse. Brewster would pick the letters up after crossing Long Island Sound by whaleboat. Upon returning to Connecticut, Brewster would pass the letter to a Sheldon’s horse courier in Black Rock, who would ride quickly to George Washington’s headquarters.

Apart from providing intelligence, Brewster was also involved with battles against the British. When Brewster arrived in Black Rock, where the first privateers were commissioned in Connecticut, it had been just months before in November, 1775, that the Continental Congress created the Letter of Marque and a list of “Resolutions” defining parameters for prize money. Privateers were authorized to capture enemy ships and its cargo.  This was called a prize of war since they could keep a percentage of the cargo. Brewster became a privateer in November of 1776, and was engaged in many boat fights. On November 13, 1780, he proudly wrote George Washington on capturing an enemy ship. “I took a prize coming home today. A fine large boat from New Haven.”

Brewster was also involved in many whaleboat wars. He was known as the “terror of the Tories”, especially for his successful nocturnal raids on Long Island, which would help protect Connecticut from British attacks. Brewster’s efforts were successful in lowering the frequency of British kidnapping and plundering expeditions carried out against the patriots in Connecticut.  Many of the British attacks against Connecticut were directed from forts built up by the British on Long Island. Therefore it was a strategy of General Washington, to target these enemy strongholds.

Of Brewster’s many expeditions the most documented ones occurred from 1779 to 1781. The attacks also involved much planning by Benjamin Tallmadge and sometimes George Washington, to execute a successful surprise attack. An important first important step was to avoid getting noticed by the vigilant Loyalist scouts while crossing the Long Island Sound. Brewster would keep his sail down and even coordinated his expeditions with the moon cycles to keep from being noticed.

The first attack organized by Caleb Brewster was against a headquarters of pro-British Loyalists on Lloyd’s Neck at Huntington harbor. The target, the firmly entrenched barracks called Fort Franklin, from which the enemy directed many attacks against the patriots in Connecticut. It was one of eight Long Island fortifications established by the British on Long Island. On a Sunday, September 5th, 1779, commanding a collection of sloops and whaleboats and one hundred and thirty of Tallmadge’s dismounted dragoons, Brewster reached Long Island at ten o’clock and attacked Fort Franklin so quickly that the patriots were able to capture five hundred Tories behind their barricades with little resistance and no loss of a patriot.

In a second attack, at Smith’s Point on the southern coast of Long Island near Mastic Beach, the target was Fort St. George, a fortification built by Rhode Island Loyalists. The mission also entailed destroying a stockpile of three hundred tons of hay, which was in reserves for the British army. Leaving on Saturday, November 18th, from Black Rock Harbor with a total of eighty men, Brewster crossed Long Island Sound. He left the whaleboats on the coast with someone to keep watch, then led the troops in a march over twenty miles across land and then successfully attacked the fort. Brewster burned the hay stockpiles without a man killed in the expedition. Washington congratulated Brewster and Tallmadge, saying of the hay, that it must be “severly felt by the enemy at this time,” as winter was approaching.

A third attack on Tuesday, October 9, 1781, was against a group of Tory woodcutters. The target was Fort Slongo in north, central Long Island, and involved one hundred and fifty dismounted dragoons. The attack was successful with no patriot troops lost in battle.

Caleb Brewster’s role in winning the War of Independence has not been fully assessed by historians. This is due to the fact that the existence of the Culper Spy Ring itself was hidden for approximately 150 years. The heroic story of Brewster and the other members of our nation’s first espionage ring has therefore not become part of the legends of the American Revolution. Their achievements and contribution in the War of Independence were at least equal if not exceeding those of the legendary patriotism of Paul Revere.  In fact, the intelligence used in defeating the British and the very horse ride (55 miles from Manhattan to Setauket, Long Island) was more extensive than the famous horseback rides of Revere. Today, the degree of importance of the ring and its spy members is still being studied, thus there are sometimes references to the spy ring is as a “tale untold.”

The existence of the spy ring was not known until the 1930s. After the Revolution ended, no one revealed the double life that the spies led, nor their secret agent numbers or aliases. It was not until September 1930, that a Long Island historian matched signatures of the spies to their actual names. The researcher, Morton Pennybacker, was studying a merchant from Long Island and realized that George Washington’s spy correspondence matched the writing style of what was once considered to be this obscure, local merchant.

Caleb Brewster’s achievements were as noteworthy as his distinguished ancestors. He was born in Setauket, Long Island on September 12, 1747. His grandmother, Sarah Ludlow, was the wife of Roger Ludlow, the English lawyer, magistrate, military officer, and colonist who helped found the Colony of Connecticut as well as the town of Fairfield. Caleb is related to the celebrated William Brewster, the Elder, and highly esteemed member of the Plymouth Colony, who arrived on the Mayflower passenger and was the only such passenger with a university education.

Caleb Brewster married in 1783 to Anne Lewis, daughter of Jonathan Lewis, a shareholder in the Middle Wharf in Black Rock. He became a blacksmith, often trading with the Black Rock merchant Thomas Bartram, and became Captain of the first United States Coast Guard revenue cutter ship for the district of New York from 1793 to 1816. Main Street in the historic Black Rock Harbor village was renamed after Caleb Brewster in 1901 and is now called Brewster Street.


Danenberg, Elsie Nicholas, Naval History of Fairfield Country Men in The Revolution, A Tale Untold, Fairfield Historical Society, 1977

Rose, Alexander, Washington’s Spies, The Story of America’s First Spy Ring, Bantam Dell, 2006

Radune, Richard, Sound Rising, Long Island Sound at the Forefront of America’s Struggle for Independence,

Mather, Frederick Gregory, The refugees of 1776 from Long Island to Connecticut, B. Lyon Company, printers, 1913.

Various articles by Historian Beverly Tyler, Education Chair of the Three Village Historical Society. Setauket, New York, Long Island.

Web site on Black Rock history:


Robert Foley
Robert Foley is an independent scholar working on Bridgeport history topics. He is an advocate of preserving primary source documents and using new media to generate awareness on local history.