 of Fairfield in 1779. Unfortunately, Washington was unable to respond in time because he was away inspecting the troops for several days.
Timing was essential for intelligence to be of any use. Delivery time was reduced to one week when Washington’s cavalry was stationed close by, in the Greenfield Hill section of Fairfield. Having a mounted horseman ready to deliver messages that Brewster picked up from across Long Island shortened the total delivery time of spy letters picked up from New York. The new express delivery service utilized Washington’s cavalry, the 2nd Continental Light Dragoons, Sheldon’s Horse that had been commissioned by the Continental Congress on December 12, 1776 and named after Colonel Elisha Sheldon. The cavalry is still in existence today. The espionage ring provided messages and spy letters originating in New York, then carried 55 miles from Manhattan to Setauket by horse. Brewster would pick the letters up after crossing Long Island Sound by whaleboat. Upon returning to Connecticut, Brewster would pass the letter to a Sheldon’s horse courier in Black Rock, who would ride quickly to George Washington’s headquarters.
Apart from providing intelligence, Brewster was also involved with battles against the British. When Brewster arrived in Black Rock, where the first privateers were commissioned in Connecticut, it had been just months before in November, 1775, that the Continental Congress created the Letter of Marque and a list of “Resolutions” defining parameters for prize money. Privateers were authorized to capture enemy ships and its cargo. This was called a prize of war since they could keep a percentage of the cargo. Brewster became a privateer in November of 1776, and was engaged in many boat fights. On November 13, 1780, he proudly wrote George Washington on capturing an enemy ship. “I took a prize coming home today. A fine large boat from New Haven.”
Brewster was also involved in many whaleboat wars. He was known as the “terror of the Tories”, especially for his successful nocturnal 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