The Pirates of Charles Island

Tales of Old and Gold


Ronan Smith

Pirate Paradise: Charles Island in the afternoon.

     The sea and ocean trade has long been at the forefront of human history, and it is said that whenever a shark swims, there will always be a leech on its belly. In the case of oceangoing trade, that leech was, and in parts of the world still is, piracy. 

     Piracy and its actors, pirates, have been around for thousands of years, in many forms, having touched the lives of such diverse people like Julius Caesar, Captain Phillips, and even many 1600’s Milford residents. 

     Throughout the late 1600s and early 1700s was the time known as The Golden Age of Piracy, which took place in locations like the Caribbean, Bermuda, the Carolinas, and even as far as Nigeria and other parts of Africa. However, pirates did make it far more north than movies and popular depictions would have you believe, even as far north as Milford.

     In the evening, one 1699 day in Milford, a man came up from out of the docks in Milford Harbor and began walking down the street: It was the infamous pirate, Captain William Kidd. 

     While seeing ship captains in the harbor was an ordinary sight to the dockworkers and civilians at the time, Captain Kidd was anything but ordinary. He had just sailed in from Gardiners Island in New York and was making his way to Boston.

     It is said in the book, History of Milford, Connecticut, that “he put in at Milford about seven o’clock one evening, strode up the street, and boldly kissed a young lady.” 

     This was extremely taboo at the time, and still is in most cases, and likely could have gotten him attacked if he were not a man with a piracy reputation like his. This only added to his secret mystique as he would eventually leave Milford, but not without a stop on Charles Island. 

     Now what happened on Charles Island is still a mystery, but the leading theory is that he left some of his treasure from his piracy, possibly thousands of dollars of gold on the island. 

     An article written in 2013 for the Hartford Courant mentions the possibility stating, “Later, Kidd would claim that the treasure found was only part of his stash and that if he was not executed, he would lead authorities to the rest and give it to the English Crown.”

     After he was executed for piracy, it was said that his ghost came to defend the stash., a travel website, claims: “Kidd left a second curse that would befall anyone who might disturb his treasure before he returned, so it hasn’t ever been found.” 

     This could be why no remains of the treasure have been publicly found, and it may be why the island suffers so many misfortunes. From the colonial era when buildings would burn down and people would go missing, and even up to recent times, where the island was nearly destroyed by Superstorm Sandy in 2012.

     Other sources agree with these claims, including the famous Atlas Obscura, which says of Kidd and the island, “It is known that he buried treasure on Gardiner Island in New York, but it was thought that the canny pirate may have thought to divide his loot, with a portion stashed here.” 

     This would fit his depiction as a very clever and mischievous pirate, as nearly every good pirate of the time had to be. To maintain their money, ships, and people, cleverness took center stage.

     Adding to the mystery, there is another legend of treasure on the island, where some Connecticut sailors are said to have stolen some Aztec treasure, mostly gold, found in a cave in Mexico. This is very similar to the story of the Black Pearl in the Pirates of the Caribbean movie franchise.

     Out of five Connecticut sailors who supposedly discovered the riches, four died in quick succession and the last man, in a bid to remove the curse before it claimed him too, supposedly buried the treasure on Charles Island. 

     Milford is a city that, due to its age and location in the middle of Long Island Sound, will always be full of secrets, legends, and endless tales of the terrifying and mind-boggling. 

     Did Captain Kidd actually bury his treasure a mere arm’s length away? And if so, is it still there? Are the supposed curses by the pirates on the island real? We may never know, but it is an interesting scenario to think about; and if it is as true as sources at the time claim, there may be thousands of dollars and priceless historical treasures just a sandbar’s walk away.