Caleb Brewster Row Row Row's His Boat

Caleb Brewster Row Row Row's His Boat

Caleb Brewster was a member of Washington’s Culper Spy Ring.

Additionally, Brewster served in several battles in and around Long Island, receiving a wound during his time with the Continental Army which would haunt him the rest of his life.

“I certify that in the year 1778, whilst the American Army lay at the white plains, it became necessary to station an officer & a few men, on the Sound to keep open a communication with the City of New York by the way of Long Island, for the purpose of my secret corrispondence: that Capt: Lt Brewster of the 2d regiment of Artillery was chosen for this service—that circumstances made it necessary to continue him therein until the close of the War—and as far as I know or believe—that he conducted the business with fidelity, judgment & bravery, having received a wound whilst he was on that duty, of which, I am informed, he is not yet recovered” – George Washington, June 10, 1784


In the aftermath of the Revolutionary War, many soldiers (and most officers) were looking to receive compensation for the years of service they dedicated to their country. After all, these years were not spent working and, therefore, many of their businesses suffered.

The above letter was written by George Washington to justify Caleb Brewster’s request of repayment. Although he participated in several battles, most of Brewster’s work for the Continental Army was the ‘secret corrispondence’ to which Washington refers.

Caleb Brewster was a member of the Culper Spy Ring, Washington’s most successful network of spies gathering intelligence on the British. Since this was done in secret, Brewster needed Washington’s certification to verify his participation.

Culper Spy Ring

Caleb Brewster was an independent minded young man from Setauket, NY when approached by his old friend Benjamin Tallmage. Tallmage was able to recruit Brewster to join a special division of the Continental Army.

Tallmage was organizing the Culper Spy Ring. Brewster was to be the point man between Abraham Woodhull (head of information in Setauket) and the Continental army. He would row across the Long Island Sound by night, retrieve information, and return to Connecticut.

Then he’d row back to Long Island.

Then he’d row back to Connecticut.

Then he’d row back….

Brewster would then send a messenger (and often ride himself) to Tallmage on the west side of the Hudson. Sometimes, Brewster would deliver intelligence to directly to General Washington, not something often done by a Lieutenant.  

Battle of Fort St. George

More notably, Brewster joined Tallmage as a leader in the Battle of Fort St. George.

Fort St. George was built for the protection of many Rhode Island Loyalists who were evacuated when the British left that State. The Manor at St. George was fortified and turned into a garrison.

Brewster used the Spy Ring’s reconnaissance to determine the Fort’s vulnerability and a raid was organized. Less than one hundred men followed Caleb’s route across the Long Island Sound, traversed the forty miles to the south shore, and overtook the Fort without losing a single man.

As Tallmage’s report states, “The van of the detachment which carried axes to beat down the obstructions, were led by Lieutenant Brewster.” This means that Caleb was in charge of destroying the fortifications, allowing the rest of the soldiers in to fight the Battle.

While the Continentals brought their captives back to the north shore for removal to Connecticut, Brewster and Tallmage broke off from the group. The two went to Corum, NY where the burned ‘more than three hundred tons’ of hay. This hay was destined for New York City where it was needed to feed British horses and, therefore, a gigantic loss to the enemy. (Also, this is the closest Revolutionary War activity to the house in which I grew up so I kind of have to make a big deal about it)


Caleb Brewster remained in the Continental Army through the end of the war.

Brewster also patrolled the waters of the Long Island Sound with a whaleboat and several men. Caleb engaged in several minor skirmishes, generally disguising himself as a thief so as not to give away the Culper Ring.

However, in December of 1782 (more than a year after the ‘end of the war’ at Yorktown), Caleb led three whaleboats against a small group of British in the Sound. Brewster was shot through the chest and, though he survived, would suffer from the wound for the rest of his life.

Revenue Marine

Almost a decade later, Caleb Brewster was successfully placed on the invalid (disabled) list, which increased his pension.

Although he started a new Career as a blacksmith in Connecticut, Brewster was hired by the treasury department for his boating skills. He was hired by the Revenue Marine to enforce the Treasury Department’s tariffs.

Other than resigning for three years in protest of the policies of John Adams, Caleb Brewster would command a ‘cutter’ for the United States for almost two decades.

If you would like to learn more about the Culper Spy Ring, check out my article on Austin Roe or my review of the Spy Trail Tour in Setauket, NY.

To learn more about Caleb Brewster, the best casual reading can be done with the fantastic book ‘Washington’s Spies.’ I love this book (though I’m partial because much of it took place by my hometown) and can’t recommend it enough. Pick it up through the affiliate link below.

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