Off The Trails: A Hiker's Guide to the Outdoors

Charles Island

Milford, CT

Difficulty: Easy

WARNING: CONSULT A TIDE CHART BEFORE ATTEMPTING TO REACH THE ISLAND. INCORRECTLY TIMING THE TIDES CAN LEAD TO SERIOUS INJURY OR DEATH. ATTEMPT AT YOUR OWN RISK.

If you ever stood on the shores of Long Island Sound in Milford, CT, then you’ve probably seen the island not to far in the distance called Charles Island. This 14-acre island is home for many locally endangered species. However it’s not the birds that gets locals fascinated, it’s the history and urban legends! Charles Island, once known as Poquehaug, is steeped in local legends involving pirates, curses and buried treasure!

Accessing the island can be challenging. At low tide a sand bar is exposed allowing beach goers to walk the half mile distance to the shores of Charles Island. Boaters and kayakers have their own challenges when getting to the island. Shallow rocks pose navigational hazards and create strong west to east currents that can easily overtake an experience swimmer or kayaker. For example, kayaking from the western side of Milford (near Stratford) to the island can take about 20 minutes. However, the return trip can take 90 minutes.

Charles Deal purchased the island in 1657 for use as a tobacco plantation. In the early 1850s, Elizur E. Pritchard of Waterbury built a summer hotel and resort near the center of the island. The hotel included a bowling ally, swimming pool, bars, fountains, cherry trees and gardens and was accessible by sandbar or steamboat. Sadly, the start of the Civil War was the demise for the resort which closed in 1868 and the buildings and a local fertilizer facility succumbed to fires in the 1880s. The 1900s came and went along with other plans for the island, which included an amusement park and a power station. The last occupants were in the 1930s when the island served as a catholic men’s retreat. The ruins of their stone structure are all that remain from the islands past.

However, the history of Charles Island is also steeped in legends. In 1699 the famous pirate Captain Kidd was sailing from New York to Boston to face piracy charges. On his way he stopped on Gardiner Island on the edge of Long Island to bury his treasure as an insurance policy before his trial. During his trial this treasure was recovered and used as evidence. Kidd talked about having hundreds of thousands of euros worth of treasure. However, his loot on Gardiner Island only totaled about 14,000 euros. So where is the rest?

Fast forward to 1889 in the attic of one of Milford’s oldest houses, a letter is discovered detailing Captain Kidd’s visit to the coastal town in 1699. The letter was written by a young woman named Patience Tuttle. She describes the pirate as being uncivil and vulgar. At one point in the letter she says “he came in ye room, put his arms about my waiste and kissed me.” Later she says “I overheard Jocobeth say yt Kidd was going on a long cruise, and yt he had left some things with him. I am going to tell Aunt Prudence all about it, and find out what they are.” The letter also details these items are buried near “Hog Rock” which was a landmark rock on the southern side of Charles Island. It’s unclear who “him” or “Jocobeth” are in the letter. Historians don’t even know for sure who discovered the letter or the exact house it was found in. They aren’t even sure if the letter is authentic, or an elaborate hoax; and no one knows where the letter is today and some even doubt its existence.

The story doesn’t end there. Legend says Kidd cursed the treasure, bringing misfortune to anyone who finds it. Sometime in the 1800s two treasure hunters were digging on the island near Hog Rock, when they struck an iron chest. Instantly, a flaming skeleton emerged from the ground and a headless man descended upon them from the sky. The hole erupted in blue flames. The two terrified men dropped their tools and took off. The next day they returned to find their tools gone and the hole filled in. No one has ever dug for treasure since.

Captain Kidd’s legend isn’t the only legend to place a curse on the island. Native American chief Ansantawae cursed the island after selling land in exchange for his kidnapped daughter. His curse stated no building will ever survive on the island, and so far, that has been true. In the 1700s a Mexican emperor had his treasure stolen by 5 men. The emperor cursed them as revenge. Four of the men mysteriously died, the 5th made his way to Charles island and buried the remaining treasure and the curse.

Captain Kidds treasure on Gardiner Island and his voyages from Oyster Bay to Boston are all well documented facts; and after settling in New York it’s likely Kidd spent some time in Milford and along the coast. Gold coins, rings and jewelry (both Mexican and Spanish) believed to be from the 16-1700s have been discovered along the Milford coastline and surrounding towns, giving credence that at least some of the legends are rooted in fact. Whether you believe in the legend of Captain Kidd, or the Mexican Emperor, one thing is true, the island isn’t giving up its secrets anytime soon. Stories like these get passed through the generations and help influence the local culture, and regardless if they are true or not they make a great ghost story.

Parking: 1 Silver Sands Pkwy, Milford, CT, 06460

AllTrails: https://www.alltrails.com/explore/trail/us/connecticut/charles-island-trail

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