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Whaleboat War on Long Island Sound

Gentlemen — There are a couple of speakers I did not write about during the year, but that I will over the summer. 

Ed Hynes talked to Y’s Men in March about the Connecticut-Long Island Whaleboat War of 1776 — 1781. The “war” as he presented it was a few infrequent, tactical skirmishes toward the end of the Revolutionary War, something of a civil war fought between neighbors, former friends, even relatives.

The combatants were freedom seeking Patriots, descendants of the Pilgrim and Puritan first settlers of New England fighting against those aligned with the Crown, most of whom were Anglicans.

Their boats were the ones used by whale men to pursue their prey — about 25 feet long, with v-shaped hulls at both ends. They were rowed by four to ten men, and used to ferry fighters across the Sound to facilitate small, hit-and-run raids.

Prior to the first of the skirmishes the British army under General William Howe defeated Americans soldiers led by George Washington in the Battle of Long Island, in today’s Brooklyn, on August 27, 1776. The Patriots were routed in what was the biggest battle of the war, involving some 30,000 British soldiers and 20,000 Americans. This was also the first battle following the signing of the Declaration of Independence.

This defeat also gave Manhattan to the British. Washington fled south, and in December crossed the Delaware River and encamped for the winter of 1776-77 in Princeton to rebuild his army.

In October, 1776 Connecticut’s General Assembly ratified the Declaration of Independence and made opposition to the Patriot cause treason, punishable by death.

Following the British victory and Connecticut’s ratification many of its Anglican churches closed and their congregants moved to New York, which had been Anglican since the end of the 17th century, and to Long Island, while Patriots left New York for Westchester and Connecticut.

The Whaleboat War began in 1777 with a raid led by colonial Colonel Return Jonathan Meigs, from Guilford to the North Fork of Long Island. With 234 men, he raided Sag Harbor, burned 12 ships, destroyed over 100 tons of food, killed six Loyalists and took 90 prisoners — with no Patriot losses.

Mr. Hynes jumped forward two years to his next raid, in May, 1779. Tories from Suffolk County retaliated by attacking Fairfield and capturing General Gold Selleck Silliman. He was held prisoner for six months, until the colonials captured New York Judge Thomas Jones to enable an exchange. Interestingly, that raid was led by Captain David Hawley, a forebear of Y’s Man Joe Hawley.

The most consequential of the battles, two months later, and the only one involving a standing army, was led by British Major General William Tryon. He sailed from New York with 2,600 troops, wreaked havoc on New Haven, Fairfield and Norwalk, destroyed Patriot armaments, terrorized residents, and burned Fairfield to the ground, trying — unsuccessfully — to draw General Washington from the Hudson Highlands.

Caleb Brewster, who was a colonial spy, led numerous raids, including on in September, 1779, when he led 130 Patriots on a raid of Fort Franklin on Lloyd Neck. His surprise was so great that he captured 500 Tories without losing a man. 

In November, 1780 Major Benjamin Talmadge — for whom Brewster worked — led a raid on Brookhaven, Long Island, were his party burned a British fort and torched 300 tons of hay the British had gathered for the winter.

In the final raid Mr. Hynes presented, in July, 1781, a Tory party surrounded the Middlesex (Darien) Meetinghouse during afternoon services. One of the raiders, a man the worshippers knew, called for them to come out and surrender. As they did, their valuables were taken and 48 men were taken prisoner.

To this writer it is not clear that taken together these skirmishes were consequential. Yes, Fairfield was burned, people were killed, weapons were taken, and men were imprisoned, but as Mr. Hynes presented the story, it is not clear that the raids had an impact on the outcome of the war.

Photo by Ted Horowitz

Roy Fuchs