 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 18th, 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 