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Battle of New York Account by Benjamin Tallmadge of Connecticut. - History

Battle of New York Account by Benjamin Tallmadge of Connecticut. - History

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Crossing the East River
This was the first time in my life that I had witnessed the awful scene of a battle [Long Island], when man was engaged to destroy his fellow-man. I well remember my sensations on the occasion, for they were solenm beyond description, and very hardly could I bring my mind to be willing to attempt the life of a fellow-creature. Our army having retired behind their intrenchment, which extended from Vanbrunt's Mills on the west to the East River, flanked occasionally by redoubts, the British army took their position, in full array, directly in front of our position. Our intrenchment was so weak that it is most wonderful the British general did not attempt to storm it soon after the battle in which his troops had been victorious.

Gen. Washington was so fully aware of the perilous situation of this division of his army that he immediately convened a council of war, at which the propriety of retiring to New York was decided on. After sustaining incessant fatigue and constant watchfulness for two days and nights, attended by heavy rain, exposed every moment to an attack from a vastly superior force in front, and to be cut off from the possibility of a retreat to New York by the fleet which might enter the East River, on the night of the 28th of August Gen. Washington commenced recrossing his troops from Brooklyn to New York.

To move so large a body of troops, with all their necessary appendages, across a river a full mile wide, with a rapid current, in the face of a victorious well disciplined army nearly three times as numerous as his own, and a fleet capable of stopping the navigation so that not one boat could have passed over, seemed to present most formidable obstacles. But in face of these difficulties, the Commander-in-Chief so arranged his business that on the evening of the 28th, by lo o'clock, the troops began to retire from the lines in such a manner that no chasm was made in the lines, but as one regiment left their station on guard, the remaining troops moved to the right and left and filled up the vacancies, while Gen. Washington took his station at the ferry and superintended the embarkation of the troops.

It was one of the most anxious, busy nights that I ever recollect, and being the third in which hardly any of us had closed our eyes in sleep, we were all greatly fatigued. As the dawn of the next day approached, those of us who remained in the trenches became very anxious for our own safety, and when the dawn appeared there were several regiments still on duty. At this time a very dense fog began tu rise, and it seemed to settle in a peculiar manner over both encampments. I recollect this peculiar providential occurrence perfectly well; and so very dense was the atmosphere that I could scarcely discern a man at six yards' distance.

When the sun rose we had just received orders to leave the lines, but before we reached the ferry, the Commander-in-Chief sent one of his aids to order the regiment to repair again to their former station on the lines. CoL Chester immediately faced to the right about and returned, where we tarried until the sun had risen, but the fog remained as dense as ever. Finally, the second order arrived for the regiment to retire, and we very joyfully bid those trenches a long adieu. When we reached Brooklyn ferry, the boats had not returned from their last trip, but they very soon appeared and took the whole regiment over to New York; and I think I saw Gen. Washington on the ferry stairs when I stepped into one of the last boats that received the troops. 1 left my horse tied to a post at the ferry.

The troops having now all safely reached New York, and the fog continuing as thick as ever, I began to think of my favorite horse and requested leave of volunteers to go with me, and guiding the boat myself, I obtained my horse and got off some distance into the river before the enemy appeared Brooklyn.

As soon as they reached the ferry we were saluted merrily from their musketry, and finally by their field pieces; but we returned in safety. In the hue; tory of warfare I do not recollect a more fortunate retreat. After ale the providential appearance of the fog saved a part of our army from being captured, and certainly myself, among others who formed the rear guard. Gen Washington has never received the credit which was due to him for this wise and most fortunate measure.

Battle of New York Account by Benjamin Tallmadge of Connecticut. - History

By Peter Kross

The American Revolution was a proving ground for American spy operations. General George Washington’s use of deception, covert activities, secret inks, and informers was a model for future spymasters.

Washington’s idea that with good intelligence a smaller force could defeat a larger one was a notion that was subsequently proven on the battlefield. Without the splendid espionage network begun by Washington, the tide of battle and the future shape of the United States might have been different.

Legend has it that George Washington never told a lie. The fact is that he told plenty of them in furthering the American cause against Britain. Washington was America’s first grand spymaster, using all the tricks of covert warfare he had learned while serving as a commander in the French and Indian War. He deceived the British on numerous occasions and ran one of the largest espionage operations in American history up to the 20th century.

Badly outnumbered by the well-trained British Army—one of the most efficient fighting forces in the world—Washington decided to use every means available to counteract his formidable foe. He realized that not only could American secret agents gather vital information on the disposition of the superior British forces, but they could give the enemy false information as well.

2. James Armistead

James Armistead Lafayette (R) at Yorktown, standing with Marquis de La Fayette (L).

During the Yorktown campaign, the Marquis de Lafayette found an unlikely secret agent in James Armistead, a black slave who got his master’s permission to assist the Continental Army. The Virginia-born bondsman began his service by transporting dispatches and intelligence reports across enemy lines. He then graduated to full-blown espionage in the summer of 1781, when he infiltrated Charles Cornwallis’s camp by posing as a runaway slave loyal to the British. He proved so convincing in the undercover role, that Cornwallis eventually enlisted him to work as a British spy. Armistead agreed and immediately began funneling the Redcoats phony information supplied by Lafayette, including a fraudulent report that referenced nonexistent units of Continental troops. He also kept his ears open for any word of enemy movements. In July 1781, he was one of the first sources to inform Lafayette that the British were marshaling their forces at Yorktown.

Despite having risked his life for his country’s freedom, Armistead was sent back to his master after the war and held as a slave for several more years. He finally won his release papers in 1787, thanks in part to Lafayette, who wrote a letter to the Virginia legislature on his behalf. As a sign of his gratitude to his former commander, Armistead later changed his name to James Armistead Lafayette.

TBR News Media hosts screening of ‘One Life to Give’

By Heidi Sutton

The 1,000-seat theater at Stony Brook University’s Staller Center was filled to capacity last Sunday night as the community came out in droves to celebrate the first screening of TBR News Media’s feature-length film, “One Life to Give.” And what a celebration it was.

“I have to say this exceeds our highest expectations. We are so thrilled,” said TBR News Media publisher Leah Dunaief, scanning the packed house as she welcomed the audience to “what has been a year’s adventure.”

“I am privileged to be the publisher of six hometown papers, a website, a Facebook page and, now, executive producer of a movie,” she beamed.

TBR News Media publisher Leah Dunaief addresses the audience.

Dunaief set the stage for what would be a wonderful evening. “I’m inviting you now to leave behind politics and current affairs and come with me back in time more than two centuries to the earliest days of the beginning of our country — the start of the American Revolution.”

“We live in the cradle of history and I hope that when you leave tonight you will feel an immense pride in coming from this area,” she continued. “The people who lived here some 240 years ago were people just like us. They were looking to have a good life, they were looking to raise their children.” Instead, according to Dunaief, they found themselves occupied by the British under King George III for the longest period of time.

Filmed entirely on location on the North Shore in 16 days, the film tells the story of schoolteacher turned spy Nathan Hale and how his capture and ultimate death by hanging in 1776 at the age of 21 led to the development of an elaborate spy ring in Setauket — the Culper spies — in an effort to help Gen. George Washington win the Revolutionary War.

Scenes were shot on location at Benner’s Farm in East Setauket, the William Miller House in Miller Place, the Sherwood-Jayne Farm, Thompson House and Caroline Church of Brookhaven in Setauket and East Beach in Port Jefferson with many local actors and extras, period costumes by Nan Guzzetta, props from “TURN” and a wonderful score by Mark Orton.

The film screening was preceded by a short behind-the-scenes documentary and was followed by a Q&A with Dunaief, producer and writer Michael Tessler and director and writer Benji Dunaief along with several key actors in the film — Dave Morrissey Jr. (Benjamin Tallmadge), Hans Paul Hendrickson (Nathan Hale), Jonathan Rabeno (John Chester) and David Gianopoulos (Gen. George Washington).

“It says quite a bit about our community that we could pack the Staller Center for a story that took place over two hundred years ago,” said Tessler, who grew up in Port Jefferson. “I hope everyone leaves the theater today thinking about these heroes — these ordinary residents of our community who went on to do some extraordinary things and made it so that we all have the luxury to sit here today and enjoy this show and the many freedoms that come with being an American.”

Director Benji Dunaief thanked the cast, crew and entire community for all their support. “In the beginning of this project I did not think we would be able to do a feature film, let alone a period piece. They say it takes a village, but I guess it actually takes three.”

From left, Jonathan Rabeno, David Gianopoulos, Hans Paul Hendrickson and Dave Morrissey Jr. field questions from the audience at the Q&A.

“Our cast … threw themselves 100 percent into trying to embody these characters, they learned as much as they could and were open to everything that was thrown at them — I’m blown away by this cast. They are just incredible,” he added.

“The positivity that was brought to the set every day made you really want to be in that environment,” said Rabeno, who said he was humbled to be there, and he was quick to thank all of the reenactors who helped the actors with their roles.

One of the more famous actors on the stage, Gianopoulos (“Air Force One”) was so impressed with the way the production was handled and often stopped by on his day off just to observe the camera shots. “I really enjoyed just watching and being an observer,” he said, adding “It was just such an honor [to be a part of the film] and to come back to Stony Brook and Setauket where I used to run around as a little kid and then to bring this story to life is just amazing.”

According to the director, the film has been making the rounds and was recently nominated for three awards at Emerson College’s prestigious Film Festival, the EVVY Awards, including Best Editing, Best Writing and Best Single Camera Direction and won for the last category.

Reached after the screening, Assemblyman Steve Englebright (D-Setauket) said the film was the essence of a sense of place. “I thought it was spectacular. I thought that it was one of the highlights of all of the years that I have lived in this community.”

He continued, “It all came together with local people and local places talking about our local history that changed the world and the fact that it was on the Staller Stage here at a public university that was made possible by the heroics of the people who were in the film both as actors today and the people that they portrayed.”

For those who missed last Sunday’s screening, the film will be shown again at the Long Island International Film Expo in Bellmore on July 18 from 2 to 4 p.m.

Filming for a sequel, tentatively titled “Traitor,” the story of John André who was a British Army officer hanged as a spy by the Continental Army during the Revolutionary War, will begin in two weeks.

Special thanks to Gold Coast Bank, Holiday Inn Express, Island Federal Savings Bank and Stony Brook University for making the evening’s screening possible.

Photos by Heidi Sutton and Rita J. Egan

Reflecting on those who made America’s independence possible

By Beverly C. Tyler

As we prepare to celebrate Independence Day, July 4, it is fitting to reflect on the actions of some of the men and women who helped win our independence.

The Revolutionary War had a great effect on the residents of Long Island. After the Declaration of Independence was signed July 4, 1776, many Long Islanders, especially in Suffolk County, received it enthusiastically. Their enthusiasm was short-lived, however, for on Aug. 27, 1776, the British took possession of New York City, following the Battle of Long Island in Brooklyn, and with its possession of all of Long Island. The residents were to be under British control for the next seven years.

“Since my arrival at camp I have had as large an allowance of fighting as I could, in a serious mood, wish for.”

— Benjamin Tallmadge

A large number of Long Island Patriots fled to Connecticut and became refugees, giving up their lands, homes and most of their possessions. Those who stayed lived under often harsh, military rule. The residents were forced to provide whatever His Majesty’s forces needed. Cattle, feed, grains, food, wagons and horses, especially cordwood for fuel was taken, and in most cases, not paid for. Long Island was virtually stripped of its mature trees during the first three to five years of the war to supply lumber and fuel for New York City.

In addition to suffering at the hands of the British, many Long Islanders were also considered fair game by their former friends and neighbors in Connecticut who would cross the Sound to harass the British, steal supplies, destroy material the British might use and take captives. The captives were often taken in exchange for the Patriots captured by the British.

Benjamin Tallmadge, Gen. George Washington’s chief of intelligence from the summer of 1778 until the end of the Revolutionary War, was born and spent his youth in Setauket, Long Island. Following four years at Yale College in New Haven and a year teaching in Wethersfield, Connecticut, Tallmadge joined the Continental Army. He took an active part in the Battle of Brooklyn and progressed rapidly in rank. As a captain in the 2nd Regiment of Continental Light Dragoons — Washington’s first fast attack force mounted on horses — Tallmadge came under Washington’s notice. By December of 1776, Washington had asked Tallmadge, in addition to his dragoon responsibilities, to gather intelligence from various spies on Long Island. In 1777 Tallmadge coordinated and received intelligence from individual spies on Long Island. (See History Close at Hand article published in The Village Times Herald May 10 edition.)

/>To memorialize one of the Culper spies, a polychrome statue of Benjamin Tallmadge sits on the peak of the Setauket School gymnasium. Photo by Beverly C. Tyler

Tallmadge was promoted to the rank of major April 7, 1777. In June Tallmadge’s troop, composed entirely of dapple gray horses, left their base at Litchfield, Connecticut, and proceeded to New Jersey where Washington reviewed the detachment and complimented Tallmadge on the appearance of his horsemen.

Washington gave the troops of the 2nd Regiment little chance to rest after they came to headquarters, and Tallmadge wrote, “Since my arrival at camp I have had as large an allowance of fighting as I could, in a serious mood, wish for.”

In September and October, Tallmadge took part in the Battle of Germantown. In November of 1777, when the American army finally went into winter quarters at Valley Forge, Tallmadge was ordered, “with a respectable detachment of dragoons,” to act as an advance corps of observation.

During these maneuvers into the no-mans-land area between the American and British lines around Philadelphia, Tallmadge again engaged in obtaining intelligence of the enemy’s movements and plans.

In January of 1778, the 2nd Regiment of Light Dragoons was ordered to Trenton, New Jersey, where the other cavalry regiments were assembling to spend the winter. Throughout the spring, Tallmadge waited for action. In June the 2nd Regiment was assigned to take up a position in advance of the American lines near Dobbs Ferry. In July Washington returned to the Hudson Valley with most of his army. With the arrival of the French fleet under Count d’Estaing in July, the pressing need for organized military intelligence could no longer be avoided. Officers, and especially dragoon officers, were encouraged to find intelligent correspondents who could furnish reliable information to American headquarters.

During the summer of 1778, Tallmadge was able to establish, with Washington’s approval, a chain of American spies on Long Island and in New York, the now recognized Culper Spy Ring, feeding information through Setauket, across Long Island Sound to Fairfield, Connecticut, and by mounted dragoon to Washington’s headquarters. Despite Tallmadge’s important role in the formation of the spying operation, his duties as field officer of the 2nd Regiment took most of his time during the summer and fall of 1778. The men and women who made the spy ring function lived in constant danger in both British and Patriot territory. We owe them the greatest respect and honor we can offer, especially on July 4.

As the war in the northern colonies settled into a stalemate, the British adopted a southern strategy, and shifted their military focus to the southern colonies in hopes of reviving their fortunes. With the war&rsquos center of gravity shifting to the south, and especially after Washington and his French allies&rsquo decisive victory at Yorktown in October of 1781, New York City, and with it the Culper Ring, became less important. The ring closed shop and ceased activities soon thereafter.

However, although Yorktown proved to be the last major battle of the Revolutionary War, the war did not officially end until Congress accepted the terms of the 1783 Paris Peace Treaty, and formally ratified it in January of 1784. Until then, George Washington remained skeptical of the British &ndash who held on to New York City until November of 1783 &ndash and their intentions. Accordingly, he ordered the Culper Ring reactivated in September of 1782, but there was not much to report. As Robert Townsend wrote on September 19th, 1782, the British had truly thrown in the towel, accepted American independence, and were just waiting for peace negotiations to conclude so they could leave.

After the war, Townsend withdrew into anonymity, and his wishes to remain anonymous were respected by those who knew of his espionage. He wrapped up his business activities in New York City, and returned to the family home in Oyster Bay, Long Island. He never married, although he fathered an illegitimate son upon a housemaid. Robert Townsend lived with his sister in Oyster Bay until he died of old age in 1838.

Abraham Woodhull got married in 1781, as the war was winding down. He had three children with his wife before she died in 1806. He remarried late in life, in 1824, before dying two years later in Setauket, in 1826. By then, he had become a man of stature in local politics, having served as magistrate of Setauket, judge of the Court of Common Pleas, and first judge of Suffolk County.

After the war, Caleb Brewster married a woman from Fairfield, Connecticut, and settled there with her, where the couple raised a family of eight children. He made a living as a blacksmith and a farmer until 1793, when he joined the United States Revenue Cutter Service &ndash forerunner of today&rsquos Coast Guard. He eventually retired to a farm in Black Rock, Connecticut, and died in 1827.

Benjamin Tallmadge served in the Continental Army until it was disbanded in 1783. He then returned to civilian life, and settled down to raise a family of seven children with his wife in Connecticut. He became a businessman and entered into a variety of business ventures, including serving as a bank president, and speculating in land in Ohio. When George Washington was elected president, he appointed Tallmadge as postmaster for Litchfield, Connecticut. In 1800, he was elected to Congress as a Federalist, and served in the House of Representatives until 1817. He died in 1835.

Where Did We Find This Stuff? Some Sources & Further Reading

John Bolton — Benjamin Tallmadge

By 1778 New York City had become the command center for all British Military Operations. Washington strategically planned a permanent spy ring in New York. He goes to Benjamin Tallmadge for assistance. Tallmadge becomes the ring leader and chooses the identification as John Bolton. John Bolton makes Setauket, Long Island the headquarters of his spy ring operation. He cleverly selects people around him to become spies. Some were farmers, shop keepers, and whomever else wouldn’t potentially raise suspicions.

Benjamin Tallmadge and Anna Smith Strong

Major Tallmadge approaches Caleb Brewster who operated a mercenary fleet of whaleboats on Long Island Sound. Brewster sends messages back and forth between Washington’s camp in Connecticut and a Setauket man named, Samuel Culper. A woman named Anna Smith Strong coordinates Brewster’s ferry schedule through secret signals hung on her laundry line.

1862 March 26: Details of the Battle of New Bern

The latest war news, this week about the Battle of New Bern, which had been fought on March 14, 1862. This is from The Prescott Journal of March 26, 1862.



The Capture of Newbern [sic]

F U L L P A R T I C U L A R S !


The following are the details of the battle at Newbern [sic] :

Commodore Rowan 1 was in command of the fleet of gunboats, and had sunken vessels, torpedoes, and other rebel obstructions to overcome and pass, but surmounted all with but slight damage to only two of his fifteen vessels. Two brigs, three barks, and ten schooners were sunk by the rebels, above two rebel batteries. The latter were silenced, the sunken vessels passed, and our flag hoisted over the silenced batteries as our force went along. This was on Saturday P. M., and night closed in.

A 10-Inch Columbiad Mounted as a Mortar, from “Harper’s Pictorial History of the Civil War𔄤

Sunday morning a heavy fog set in, but lifted, when our gunboats passed up safely and silenced Fort Thompson with its two heavy Columbiads. Then Fort Ellis with nine guns was captured after pretty brisk fighting, but the rebels fled soon in a panic, and our flag waved over another fort. Only one fort was left to be engaged and Newbern [sic] would be at the mercy of our troops this was Fort Lane—the rebels having enough of the boats, offered little if any resistance and fled. The rebels then fired a large number of scows filled with rosin and turpentine, inteding to float them down and burn our gunboats, but they got stuck and burnt away furiously. The gunboats then shelled the depot and track, but our troops had then crossed and a white flag was hoisted. Our navy did not lose a man.

Operations on land were briefly as follows : Our troops landed twelve miles below Newberne [sic], Gen. Reno’s brigade 3 in the advance. Most of the troops were so anxious to land that nearly every regiment jumped into the water and waded ashore. In less than two hours, after marching two miles, they found deserted rebel camps, with fires burning, and hot rebel breakfast untasted. A breastwork was only passed and the division bivouacked for the night, and early in the morning skirmishing began.

Foster’s brigade, 4 comprising the Massachusetts 24th, 25th, 26th, 23d, with the 10th Connecticut in reserve, were in line, and engaged a twenty gun battery of the rebels on their left flank, who showered grape, canister and shell upon them, also heavy musketry from their infantry.

The second brigade, comprising the 21st Massachusetts, 51st New York, 51st Pennsylvania and 9th New Jersey engaged them on the right, and General Clark’s third brigade 5 took a position in front. The 1st brigade bore the brunt of battle and the 24th Massachusetts soon had Maj. Stevenson and Lieut. Colonel Horton wounded, and the 23d Massachusetts lost Lieutenant Colonel Merritt by a cannon ball carrying away one side of his body. 6

The 10th Connecticut were ordered to support the 27th Massachusetts, which had suffered severely.

The 3d brigade together with the 2d executed a flank movement, and the order to charge bayonets was given.

Battle of New Bern, from “Harper’s Pictorial History of the Civil War𔄣

A hand to hand fight ensued of the most desperate character, when our troops drove the rebels out at the point of the bayonet, chasing them out of sight.

The rebels took possession of a railroad train and fled from Newbern [sic], burning some bridges, the Washington House, some private dwellings, and a number of whiskey and turpentine distilleries.

Slaves had commenced pillaging but were stopped.

A number of Unionists were found in the city.

1. Harper’s Pictorial History of the Civil War, by Alfred H. Guernsey and Henry M. Alden, Chicago: McDonnell, 1866-68 (available in the UWRF Archives E 468.7 .G87 1866).
2. Stephen Clegg Rowan (1808-1890) was a career navy man. At the start of the Civil War, he was captain of the Pawnee, and made gallant attempts to relieve Fort Sumter. He assisted in the Battle of Hatteras Inlet, the Battle of Roanoke Island, and provided support at the Battle of Elizabeth City and Edenton.
3. Brigadier General Jesse Lee Reno (1823-1862), a career military officer, led the 2nd Brigade. He will be killed on September 14, 1862, at the Battle of South Mountain. The city of Reno, Nevada, is named for him.
4. Brigadier General John Gray Foster (1823-1874), another career military officer, led the 1st Brigade. From 1862-1863 he will command the Department of North Carolina.
5. Brigadier General John Grubb Parke (1827-1900), an Army engineer, led the 3rd Brigade. William Smith Clark (1826-1886) was the lieutenant colonel of the 21st Massachusetts Infantry.
6. Robert H. Stevenson William L. Horton Henry Merritt.

By the end of that conflict he had risen to become one of George Washington’s chief intelligence officers, organizing the Culper Spy Ring out of New York City and Long Island.

This is his remarkable account of that period.

Tallmadge gives a year by year account of his experiences during the conflict from his joining the army and meeting English troops for the first time in 1776 through to Washington’s leaving the army and emotional final farewell to his officers at Fraunces’ Tavern.

He was trusted greatly by Washington and other generals, rising through the ranks and given command of large numbers of troops.

Tallmadge’s memoirs cover many of the important events that he personally witnessed during the seven years of conflict, including battles like Short Hills and Monmouth, expeditions against the British on Long Island that led to the Battle of Fort St. George as well as numerous skirmishes.

This edition sheds more light upon his espionage activities than what is given in the original memoirs. Henry Phelps Johnston, a Professor of History at the College of the City of New York, draws upon Tallmadge’s own correspondence with Washington, Heath, Gates, Clinton and other officers to further explain the Colonel’s position in the American Revolutionary Wars.

Of particular interest in the additional materials are those that relate to Tallmadge’s service between 1778 and 1783 as a spy master, the capture and trial of Major Andre and the betrayal of Arnold.

After the war Tallmadge was elected as a member of the Federalist Party to the House of Representatives. This edition of his memoirs was published with the assistance of the Society of the Sons of the Revolution. He died in 1835 in Litchfield, Connecticut.

Caleb Brewster in the Revolutionary War

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 18 th , 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.

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