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The Black Rock section of Bridgeport played a key role in the American Revolution. George Washington describes what information he was seeking in one of his first letters to Black Rock’s Caleb Brewster.  In this first letter we see how focused Washington was in preventing the British from interfering in the arrival of the French in Rhode Island…“To obtain speedy and certain intelligence of this matter may be of great Importance to the French Fleet at, and the enterprize on, Rhode Island.”  The intelligence helped General Washington and Americans to defeat the British.  Caleb Brewster was instrumental in Washington achieving this goal.

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Caleb Brewster’s role in American Revolution spy ring (Map courtesy Three Mile Village Setauket Museum)

This map illustrates the role Caleb Brewster played in the first spy ring of the United States. Brewster spied on the British in Long Island and carried spy letters from New York City to General Washington. Brewster was a crucial link in intelligence that directly led to winning the American Revolution and revealing the identify of Benedict Arnold.

The spy ring itself consisted of an American spy stationed in Manhattan, another patriot who carried spy letters approximately 55 miles from Manhattan to Setuaket, Long Island. Caleb Brewster was the final link, and carried the letters back from Long Island to Black Rock, Connecticut.

When Brewster arrived in Black Rock (then Fairfield), the letters were picked up by the Dragoons, who rode by horseback to hand deliver them to George Washington at his headquarters. The Dragoons, otherwise known as “Sheldon’s Horse, The Second Continental Light Dragoons” were commissioned by Congress under the command of Colonel Elisha Sheldon on December 12 of 1776 at the direct recommendation of General George Washington. They are still in existence today and perform re-enactments.

We are currently working on a timeline to indicate exactly where General Washington was and which of the Dragoons members were involved.  Dragoons also worked with Brewster in raids on Long Island of British forts. The Dragoon cavalry involved was led by Benjamin Tallmadge who organized the Culper Spy Ring.