The Pirates of Long Island SoundLong before movies popularized the image of them owning the clear blue waters of the Caribbean, pirates were operating right here in Connecticut, sailing through Long Island Sound and supposedly burying treasure in Milford.
What might surprise those picturing the terrorizing outlaws conjured in popular culture, however, is that they were welcomed, not feared, by merchants in shoreline communities such as New London and New Haven. The seamen who became known as pirates were then considered black-market traders necessary to the local economy due to British trade restrictions that Colonists believed to be unfair.
“What’s interesting is that every infamous pirate went up and down the Eastern Seaboard,” says pirate historian Gail Selinger, author of The Complete Idiot’s Guide to Pirates, of the era around the turn of the 18th century when Long Island Sound saw the majority of its pirate action. “The governor at the time, John Winthrop, didn’t particularly like them. But the merchants did.”
Connecticut merchants weren’t just buying from the pirates, says Selinger. They went as far as outfitting them with ships. “England wouldn’t let us trade directly with other European nations,” says Richard Radune, author of Sound Rising, which chronicles the Sound’s early strategic importance. “We basically ignored the British navigation acts and that included trade with anyone—even pirates. There was profit to be made by [Colonial] merchants who would take these goods and then sell them in their stores.”
While some pirates were engaged in trade deemed illegal under British law, others actually had official governmental authorization to operate during wartime in the interest of a particular nation. Once war ended, the activities of “privateers,” as they were known, instantly became illegal, says Selinger. Some returned to legitimate concerns, but unable to resist the lucrative opportunities of operating outside the system, many converted to piracy.
Captain William Kidd—the legendary pirate believed to have buried treasure all along the Connecticut coast—may not have been as nefarious as popularly thought. Selinger believes that he was really a privateer, commissioned in 1696 to defend British shipping. “King Charles had invested in William Kidd’s [activities], and he was supposed to go after pirates,” he says. “After months at sea, they didn’t find anybody and his crew mutinied.”
When Kidd later spotted a Dutch ship carrying French passes and goods, he attacked it. While the Dutch were neutral, France was an enemy of England.
“When he landed in the West Indies, he found out he and his ship were considered pirates [because he attacked the Dutch ship],” says Selinger. Wanting to prove his innocence—he had been, after all, commissioned by the King—Kidd sailed to New York, but not before leaving some of his fortune on Gardiner’s Island.
The Pirates of Long Island Sound
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Eventually, Kidd was captured and sent in 1699 for trial to England, where he was convicted. “He and his wife fought ’til the moment he was hanged that he did have French passes,” says Selinger. The passes would prove that the Dutch ship had been hired by the French.
In London, Kidd told authorities that if they gave him a ship under guard and allowed him to sail back to the Colonies, he would show them where he hid the remainder of the money and goods he had obtained through his endeavors, illegal or not.
Michael C. Dooling, author of An Historical Account of Charles Island, Milford, Connecticut, believes that Kidd hid riches in other locations besides Gardiner’s Island.
“He had claimed he’d hid $100,000 in treasure on various islands,” says Dooling. “According to one source, he stopped . . . and left some things with Thomas Welch in Milford.”
Legend has it that Kidd buried a portion of his ill-gotten booty on Charles Island, just off the coast of Milford’s Silver Sands State Park. No one has ever located it, however, despite many efforts.
If you’ve ever taken a cruise around the Thimble Islands, you may have heard about Kidd’s treasure there as well. “It’s said that Captain Kidd’s initials were carved in rock near a hotel there,” says Dooling. He’s also supposed to have hidden part of his hoard on Money Island—but there’s little evidence to support the claim. “In 1924, a New Haven fireman found a gold ring that was believed to have been crafted in the West Indies,” says Dooling. Could that have been a remnant of Kidd’s stash?
The Golden Age of Piracy began in the 1650s and lasted through the 1730s; in Connecticut most recorded piracy was between 1690 and 1720. The restrictive measures taken by the British government pushed merchants to find other means of engaging in trade so they could make money. “There was not a lot prior to 1680. It started to pick up around that time because you have growing settlements and growing colonies and trade was beginning,” says Radune. “The Golden Age of Piracy had to do with a number of factors, one of which was at the time, the governments (England) didn’t have the naval power to go chasing all over the world.”
As for pirates’ reputation for lawlessness and violence, there were occasional incidents in Connecticut. For instance, Fishers Island—technically in New York but located only two miles off the southeastern coast of Connecticut—was ransacked in 1690 by pirates who burned down the main house there. In a letter to the governor on July 25, 1682, Daniel Wetherell reported that about 40 pirates on two to three ships had been lurking off the coast of New London. They had attacked and took a ship with all its cargo. Pirates also went after the ship of a man named Jonas Clarke who was sailing to Long Island with cargo. “He managed to out-sail them and came into New London harbor where he asked for help. The officials were unsure what authority they had or what the governor would approve,” says Radune, so while they wouldn’t provide any men, they did give Clarke weapons to help fend off his attackers. According to the letter, Clarke seems to have gotten away—again, out-sailing the pirates.
Notorious pirate Thomas Veal was also known to have landed in Connecticut. Tying up just off New London, he and a cohort came ashore searching for weapons to purchase—and offering three times their worth, according to Radune. “In the meantime, a sloop from Virginia pulled into New London and recognized these two as pirates. By the time they could take any action, the pirates had fled.”
Later, John Prentice, the same man who had allowed Veal to come ashore, was sailing to Boston and came upon Veal and his crew loading supplies off the coast of Niantic. “The pirates raised sail and chased him,” says Radune. Prentice got away, but “three days later, he rounded the northern tip of Cape Cod and encountered Veal again. At this time, most ships would not fight pirates. They would try to get away. He decided he was going to resist.”
The two ships engaged in a gun battle at sea for about an hour. Who won? No one, really. “A thunderstorm erupted and Prentice was able to get away from the pirates and sail into Boston Harbor,” says Radune.
While piracy had allowed Colonial merchants to thrive, eventually the tide turned. “There were so many pirate ships in the water that regular commerce pretty much stopped. That’s when governors, kings and queens said, ‘Now we have to do something,’” says Selinger.
Around 1720, pirates who were engaged in illegal trade began having trouble getting their goods to the Connecticut merchants. With products not making it to rightful destinations, the support of piracy ended.
Although it’s been nearly three centuries since Long Island Sound has seen the likes of Thomas Veal, the pirate legacy is still alive. Each year Milford hosts a pirate fest that kicks off with “Captain Kidd” and a crew of brigands sailing into Milford Harbor to kidnap the mayor. Hundreds of eager pirate wannabes, young and old—often with an abundance of tricorn hats, billowy white shirts and eye patches—then take over the town for the day to celebrate “pirate life” with family activities, music, food and a scavenger hunt through downtown.
The romantic notion of ruthless, peglegged buccaneers remains popular, but it’s a far cry from the black market traders who were far more interested in doing business than walking a plank.
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