Caleb Brewster (September 12, 1747 – February 13, 1827) was a member of the Culper spy ring during the American Revolutionary War, reporting to General George Washington through Major Benjamin Tallmadge. He carried messages across Long Island Sound between Major Tallmadge and the ring's main spies on Long Island, New York, and in New York City. He also made direct reports to Washington concerning naval activities in the New York City area.

Brewster was born in Setauket, New York,^[1] a hamlet of Brookhaven.^[2] After the Revolutionary War, he was a blacksmith, an officer in the United States Revenue Cutter Service for 20 years, and a farmer. He was a descendant of Francis Brewster II, barber-surgeon of Castle Bristol, who died, presumably, on the Phantom Ship in 1646-1647 and was the son of Francis Brewster I of Wrentham Hall in Suffolk, yeoman, who died 1632 in Bristol, England.

Major Benjamin Tallmadge convinced General George Washington on August 25, 1778, that Abraham Woodhull of Setauket, Long Island, would make a good agent to gather intelligence in New York City, the British Army's headquarters and base of operations during the American Revolutionary War.^[3] Woodhull and Robert Townsend were the main agents in the Ring, alias "Samuel Culper, Sr." and "Samuel Culper, Jr." respectively.^[3] Brewster was recruited to carry messages between Woodhull and Tallmadge,^[4] running regular trips in whaleboats across the Sound on a variety of smuggling and military missions.

Brewster agreed to command the boat service only under condition that he be allowed to select his own boat crews.^[5] He chose several men from eastern Long island, including half-brothers David and Benjamin Dickerson who were on active duty in another command within the Continental Army. At one point, the Dickersons along with several others of Brewster’s crew were suddenly recalled to their original commands. General Washington stepped in personally to retrieve them via a personal note that highlights the importance of the operation: “To Brigadier General James Clinton, Headquarters, Nov 8, 1778, Dear Sir: I am informed by General Scott that some boatmen belonging to your brigade who were employed by Lt. Brewster in navigating from the main to L I have been remanded to their regiments, in consequence of which a service of a particular nature is very much impeded if not entirely stopped. The names of the men Gen. Scott tells me are David Dickinson, Focanah Hawkins, Benja. Dickinson, Jonathan Kinner & Joshua Davis. I beg that you will order them back to their late duty under a careful & attentive sergeant.”^[6]

Anna Strong's role in the Ring was to signal Brewster that a message was ready, according to widely accepted local and family tradition. She did this by hanging a black petticoat on her clothesline at Strong Point in Setauket, which Brewster could see from a boat in the Sound and Woodhull could see from his nearby farm.^[7][8][9] She would add a number of handkerchiefs for one of six coves where Brewster would bring his boat and Woodhull would meet him.^[10][11][12]

In February 1778, Brewster sent a message of his own through the Culper channel that described flat-bottomed boats being built in New York that could be used to ferry troops, and Loyalist privateers being outfitted.^[13] On another trip, he was waiting for Woodhull in Anna Strong's back garden^[14][15] when he surprised a passing British lieutenant. Brewster pulled him off his horse and had the opportunity to capture or kill him,^[15] but he refrained from doing either in order to avoid drawing suspicion on Anna as a member of the Ring, and instead pretended that he and his men were thieves.^[14][15]

Brewster also participated in military actions as a Continental Army officer serving under Tallmadge.

Brewster married Anne Lewis of Fairfield, Connecticut, after the war and moved to Fairfield with her,^[16] where he set up a blacksmith business.^[17] The couple had eight surviving children.^[17]

In 1793, he joined the United States Revenue Cutter Service, predecessor of the United States Coast Guard.^[17] He took three years off from the service because he disagreed with policies of President John Adams, and he commanded the revenue cutter USRC Active (1812) from 1812 to 1816.^[17] He retired to his farm in Black Rock, Connecticut.^[17]

Brewster died February 13, 1827, aged 79, and is buried in Fairfield Cemetery.^[17]

Caleb Brewster is played by Daniel Henshall in the TV series Turn: Washington's Spies, on AMC.

• Intelligence in the American Revolutionary War

• Baker, Mark Allen (2014). Spies of Revolutionary Connecticut: From Benedict Arnold to Nathan Hale. Charleston, South Carolina: The History Press. ISBN 978-1-62619-407-6.
• Brady, Kevin M. (2013). "Culper Spy Ring". In Frank, Lisa Tendrich (ed.). An Encyclopedia of American Women at War: From the Home Front to the Battlefields. Santa Barbara, California: ABC-CLIO. ISBN 978-1-59884-444-3.
• Brewster, Caleb. "Caleb Brewster Papers, 1755–1976". Fairfield Museum and History Center. MS 33. Retrieved March 17, 2013.
• Mather, Frederic Gregory (1913). The Refugees of 1776 from Long Island to Connecticut. Albany, New York: J. B. Lyon. p. 278. ISBN 978-1-55613-342-8.
• Naylor, Natalie A. (2012). Women in Long Island's Past: A History of Eminent Ladies and Everyday Lives. Charleston, South Carolina: The History Press. ISBN 978-1-60949-499-5.
• Nelson, David Paul (2011a). "Culper Ring". In Hastedt, Glenn P. (ed.). Spies, Wiretaps, and Secret Operations. Vol. A–J. Santa Barbara, California: ABC-CLIO. ISBN 978-1-85109-807-1.
• Nelson, David Paul (2011b). "Robert Townsend". In Hastedt, Glenn P. (ed.). Spies, Wiretaps, and Secret Operations. Vol. A–J. Santa Barbara, California: ABC-CLIO. ISBN 978-1-85109-807-1.
• Owen, David (2002). Hidden Secrets. Toronto: Firefly Books. ISBN 978-1-55297-564-0.
• Phelps, Mark Anthony (2013). "355". In Frank, Lisa Tendrich (ed.). An Encyclopedia of American Women at War: From the Home Front to the Battlefields. Santa Barbara, California: ABC-CLIO. ISBN 978-1-59884-444-3.
• Rose, Alexander (2007) [2006]. Washington's Spies: The Story of America's First Spy Ring. New York: Bantam Dell. ISBN 978-0-553-38329-4.
• Welch, Richard F. (2014). General Washington's Commando: Benjamin Tallmadge in the Revolutionary War. Jefferson, North Carolina: McFarland. ISBN 978-0-7864-7963-4.

• The Caleb Brewster letter correspondence including with George Washington