 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: http://www.blackrockhistory.org/