By John Reese
At the January 28 meeting of the Retired Men’s Association Larry Allen introduced the speaker, historian Ed Hynes, a resident of Stamford, whose talk was titled “Warfare on Long Island Sound During the American Revolution.”
Hynes vividly described the Revolutionary War’s “Whale Boat Wars” on Long Island Sound. He transported his audience to a time when the Sound was a treacherous no-man’s land, its dark waters traversed nightly by armed men in small boats seeking plunder, prisoners, and revenge. Drawing on newly discovered scholarship—including a 2021 doctoral dissertation that added 165 pages of fresh material to his research—Hynes illuminated one of the Revolution’s most overlooked theaters. The warfare on Long Island Sound, he argued, may have done more to pressure King George III toward peace than many larger, more celebrated battles.
The conflict was fundamentally a civil war fought between former neighbors. When Connecticut passed laws requiring loyalty to the patriot cause in 1775, many Loyalists fled to Long Island. When the British seized New York and Long Island in 1776, they expelled the Patriots, who retreated to Connecticut.
Connecticut became the epicenter of American privateering; its long coastline was dotted with shallow harbors where British warships could not follow, and the British had inadvertently trained many local sailors during the French and Indian War. The primary weapon was the whale boat—a roughly 25-foot vessel, typically manned by ten rowers, quiet and highly maneuverable. Two or three could overwhelm a much larger British vessel by approaching silently at 2 a.m., climbing the sides, and subduing the guards before locking the sleeping crew below deck. For every ship the British captured from the Americans, Hynes reported, the Patriots took seven in return—a ratio so lopsided that Lloyd’s of London continuously raised insurance rates.
To try to suppress this privateering there were attacks across the Sound. “Now you have people on either side of Long Island Sound,” Hynes observed. “They know exactly where everybody lives, they know who had silver and where they kept it.” The human cost of capture was staggering. In March 1777, Loyalist Stephen Hoyt crossed the Sound with 25 men and kidnapped Samuel Richards, a prominent 60-year-old from Norwalk, along with 14 men found sheltering in his barn. They were taken to the notorious sugar houses and prison ships of New York City. Richards was paroled four months later, but the conditions had so broken his health that he died shortly afterward. One survivor, Levi Hanford, later dictated a gripping account of his imprisonment; it was published in the New York Times in 1852. Hynes offered a startling statistic: while roughly 4,500 men died in combat during the Revolution, over 11,000 perished in British prisons from starvation and disease.
Colonel Return Jonathan Meigs led a celebrated retaliatory attack on Sag Harbor in May 1777, dragging whale boats across the North Fork of Long Island and surprising the British garrison at 2 a.m. Meigs captured 90 prisoners without losing a single man—earning a ceremonial sword from the Continental Congress.
The kidnapping of Brigadier General Gold Selleck Silliman from his Fairfield home in May 1779 demonstrated how personal the war had become. One of his nine captors had previously worked as a carpenter on Silliman’s farm. With no prisoner of equal rank to exchange, Patriots raided Long Island to capture Judge Thomas Jones, a prominent Loyalist. The two men—classmates at Yale in 1753—were exchanged in the middle of Long Island Sound in spring 1780. Jones’s family is why we call it Jones Beach.
The British responded with a scorched-earth policy. In July 1779, forces under William Tryon devastated New Haven, Fairfield, and Norwalk in rapid succession. Fairfield, then the region’s most prominent town, never fully recovered.
In July 1781, Loyalist raiders demonstrated chilling tactical sophistication in an attack on the Middlesex Meeting House. Captain Frost led 35 men across the Sound on a new moon, knowing that in Norwalk, high tide falls at midnight and noon during such phases. They hid in nearby fields, let the 10 a.m. service pass undisturbed, then surrounded the church during the 2 p.m. service. They stripped the women of valuables and released them, then marched 49 men and 40 horses to Contentment Island. Timing their arrival for 6 p.m. low tide, they walked across the exposed mudflats to the Fish Islands and waited for the tide to rise. Hours later, ships from Long Island collected prisoners, horses, and raiders alike. Two days later, knowing every able-bodied man from Middlesex was imprisoned, the British returned and plundered every farm.
The Norwalk Islands also served as a base for American espionage. Nathan Hale departed from there on his ill-fated mission. Major Benjamin Tallmadge ran the Culper Spy Ring from nearby. The shallow waters provided perfect cover—the British simply could not pursue.
Benedict Arnold’s attack on New London and Groton in September 1781 represented the war’s nadir. Arnold, who had grown up nearby in Norwich, used his knowledge of American signal codes to confuse the defenders. When the forts fired two cannon shots to warn of approaching enemies, Arnold ordered a third shot from his fleet—the all-clear signal. The confusion allowed British forces to overwhelm the defenders at Fort Griswold in what became a massacre. Both towns burned.
Yet 1782—after Yorktown had effectively ended the war elsewhere—proved the most violent year on Long Island Sound. “In 1776, most of these guys were fighting for principles,” Hynes observed. “By 1782, they were just fighting to kill the other person.” He described a battle between Loyalist Joseph Hoyt and Patriot Caleb Brewster, each commanding two whale boats, that left every single participant killed or wounded. When the war finally ended, Loyalists who had been most active in the raids were forced to flee to Nova Scotia; their neighbors refused to let them return home.
The presentation concluded with a stimulating question and answer period.
The RMA’s next presentation, “How Did He Get the Shot? The Photography of New York Times Breaking News Journalist Neil Vigdor” by Neil Vigdor, is scheduled for 11 AM on Wednesday, February 11, 2026. RMA presentations are held at Christ Church Greenwich, Parish Hall, 254 E. Putnam Avenue, Greenwich, CT 06830.
When he’s not on deadline writing for The New York Times, chances are Neil Vigdor is chasing the shot: fireflies, star trails, the moon, Manhattanhenge, the Thunderbirds or a snowy owl. Join us for a conversation with Neil about his adopted craft, photography. He will talk about the meticulous planning that goes into capturing “wow” moments, the creative process, the gear, tips — and journalism.
Neil Vigdor is a reporter for The Times covering breaking news, with a focus on politics. His role involves a mix of reporting on politics and the Trump administration, explanatory journalism, and contributing to live coverage. The breadth of his assignments extends to stories about crime, business, pop culture, and other topics. Previously, Neil was a member of The Times political team that covered the 2024 election and the 2022 midterms. He reported from every battleground state during the last election cycle, plus Iowa and New Hampshire. He also tracked voting legislation and kept tabs on threats against election officials. Before politics, Neil covered a wide range of breaking news stories for The Times, including the police killing of George Floyd, the Jan. 6th attack on the U.S. Capitol, several mass shootings, pandemic-related news, and more.
Neil graduated from Vanderbilt University in Nashville, Tenn. He covered Connecticut and national politics for The Hartford Courant and Hearst (including Greenwich Time), reporting on four national conventions and two inaugurations. When he is not reporting, Neil moonlights in celestial and street photography. His work can be viewed on his website at neilvigdor.photoshelter.com.
To stream the presentation by Neil Vigdor at 11 AM on Wednesday, February 11, click on https://bit.ly/30IBj21. This presentation will also be available on local public access TV channels, Verizon FIOS channel 24 and Optimum channel 79.
Note: The views expressed in these presentations are those of the speakers. They are not intended to represent the views of the RMA or its members.
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