Less than a mile off the coast of Silver Sands State Park in Milford, Conn., resides Charles Island — a 14-acre site that is one of the state’s “largest remaining breeding colonies of heron and egret.” Designated as an important bird area by the National Audubon Society, the island is now managed by the Department of Energy and Environmental Protection (DEEP).
Yet the island attracts much intrigue, and has for centuries, due to its connection to the mainland by a walkable tombolo — a sandy isthmus. Many people have trekked out to Charles Island at low tide (including yours truly as a teenager).
Since the 1600s, the island has been eyed as an untapped landmark for fame, fortune and even faith, housing a tobacco plantation, summer resort, fertilizer plant and a retreat center for Dominican Catholic friars. Most famously, however, Charles Island is rumored to clutch beneath its sandy shores Captain Kidd’s legendary, undiscovered treasure. And the island is considered one of most cursed sites in Connecticut.
This little, unassuming island has had many faces and is a setting for much folklore. This is its story:
‘Hard Luck Island’
To the Paugusset Tribe, who once inhabited Milford, Charles Island was called “Poquahaug,” most likely meaning “cleared land,” according to ConnecticutHistory.org. Prior to the European settlers, historians believe the tribe’s chief — Ansantawae — used the island as a summer wigwam for himself and his family. Then on Feb. 12, 1639, English settlers led by Edmund Tapp, William Fowler (unrelated!), Benjamin Fenn, Zachariah Whitman and Alexander Bryan purchased Milford, then known as Wepawaug, from Ansantawae. The price was six coats, ten blankets, one kettle, twelve hatchets, twelve hoes, two dozen knives and a dozen small mirrors, according to “The History of a New England Hometown,” which commemorated the 350th anniversary of Milford’s founding.
(Side note: Ansantawae’s signature is enshrined on Milford’s seal)
Poquahaug was included in the deed. Within 17 years, the island changed hands three times until Charles Deal — its namesake — acquired the property in 1657. He envisioned a tobacco plantation on the island, and was given approval by the local authorities as long as he did not “truck with Indians, English or Dutch” or “allow any wild sailors’ parties,” according to “The History of a New England Hometown.” However, the plantation failed to produce profits — and history has not recorded why.
The next major development on Charles Island would come nearly two hundred years later after John Harris, a wealthy New York merchant, built a 2.5-story, 35-room mansion complete with verandas and “surrounded by cherry trees, green lawns and flower gardens.” However, Harris’ stay was short lived, as the land was purchased by Elizu Pritchard, a button manufacturer from Waterbury, in 1852. Pritchard transformed the mansion into the “Island House” summer resort and a tourist destination. Excursion boats from New Haven carried day trippers — some from “as far away as Hartford” — for leisure and recreation, as the resort was equipped with a bowling alley, bar, swimming pool, an aquarium and other amenities.
But like other economic ventures on the island, the resort closed after the Civil War. Some historians suggest the island’s reputation declined as a “wholesome family resort,” while others believed it to be “too isolated to become prosperous.” Regardless, in 1868, the island transformed again, this time into a “plant which produced fertilizer from dead fish,” according to “The History of a New England Hometown.” The plant’s life was much shorter than the resort, after it was discovered to be polluting the local air and water to the locals’ dismay.
From the late 19th century to the 1930s, Charles Island was considered as a site for an amusement park and wireless station in World War I, but neither happened. Even a boxing match was canceled after the state militia and Milford Police Department caught wind.
Then in the 1930s, Dominican friars from New Haven (the same order who served St. Mary’s Parish for 135 years until December 2021) purchased the property and built a retreat for spiritual growth and reflection in the tradition of other Catholic orders — like the 1,000-year-old monastery of Mont Saint-Michel in Normandy, France; but again, like other ventures, the retreat was abandoned, though bricks and foundations still remain.
Nothing substantial has been constructed since, though the island was once considered as a site for a nuclear power plant, but was deemed too small. Today, the state owns the land — and now winged critters call the nicknamed “hard luck island” home.
Buried Treasure and Curses, Ahoy!
With all the failed enterprises on Charles Island, one might suspect the landmark is simply not viable for business or pleasure. However, some believe there are larger, more sinister forces at play for legend has it Charles Island has been “thrice cursed.”
The first was allegedly laid by Ansantawae, but stories vary on why he cursed the site of his once summer wigwam: one is that he regretted selling the island to settlers, and the other was in response to his daughter being kidnapped (though both scenarios are unsubstantiated by the historical record at present).
Another more akin to Disney’s “Pirates of the Caribbean” film series was by sailors who, in 1721, stole treasure from a Mexican emperor named Guatmozin. According to folklore, several of the men met an unknown, yet terrible fate; meanwhile the final survivor “hid the treasure in the basement of the old Milford Inn, but apparently a drunken customer came across it while searching the cellar for beer.” The story goes that in the dead of night, the sailor “rowed out to the island and buried the booty, thereby imposing the last mighty curse upon the already beleaguered island.”
However, the most famous curse was (apparently) uttered by Captain William Kidd, a late 17th century Scottish pirate. Once a royally commissioned sea captain tasked to hunt pirates, Kidd turned to piracy after failing to capture a “prize ship” during his legitimate career as a privateer. In January 1698, however, he took the Quedagh Merchant, an Armenian ship, which included gold, silk, opium, sugar and, reportedly, “other riches, rumored to have been worth 70,000 pounds.” The ship became his most valuable prize, but also led to his eventual downfall, as the Quedagh Merchant belonged to the British East India Company. After hearing accusations of piracy, Kidd traveled to New York City in the newly purchased ship — the Antonio — to clear his name with the colonial governor of New York. Instead, the pirate was arrested, shipped back to England and hanged on May 23, 1701.
Yet, before he was forcibly shaken off this mortal coil, Kidd buried his treasure of “iron chests filled with gems and gold” on Charles Island, at least according to legend. To prevent others from finding his loot, he cursed the island “believing if you curse the land, you’ll scare off any would be treasure hunters” (or so says this Milford Mirror article). So far, no one has found the riches.
Perhaps the island is actually the most cursed place in the world! Yours truly is not willing to find out, viewing Charles Island comfortably from the Silver Sands boardwalk — or maybe it’s time to invest in a metal detector (or buy a Powerball ticket).
Till next time —
Your Yankee Doodle Dandy,
What neat history do you have in your town? Send it to yours truly and I may end up highlighting it in a future edition of ‘Hidden in the Oak.’ Please encourage others to follow and subscribe to our newsletters and podcast, ‘Y CT Matters.’