Charles Island is part of Silver Sands State Park off the coast of Milford, CT. The island is named for it's first owner Charles Deal who bought it in 1657.

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The island's history is littered with tragedy and misfortune. Locals will tell you that these events are not bad luck or some big coincidence, they say the island is cursed.

In my opinion, there is only one storyteller that I can trust with a take like this, Mike Allen. Allen is a Connecticut researcher, historian and former news man for I-95. Mike is also the host of the famous podcast "Amazing Takes From On and Off Connecticut's Beaten Path." We asked Allen to join us on the I-95 Morning Show to help us unpack the story of Charles Island.

Mike Allen
Mike Allen

Allen joined the Ethan, Lou & Large Morning Show on Tuesday (3/7/23) and designed a timeline for our listeners. Below is some of what Allen shared with us:


Charles Deal purchases the island for the purposes of starting a tobacco plantation. Deal was able to thrive there for some time but after about 15 years it failed despite the popularity of tobacco products. It is unclear why the plantation eventually folded.

The Next Century (Roughly)

According to Mike Allen, the property "laid fallow" for the next century. However, it is during this period that people believe a pirate paid a visit to the island leaving behind  his treasure. Captain Kidd was a Scottish Pirate who many people believe left of portion of his riches on Charles Island. According to legend, Captain Kidd cursed the island before he was captured.


A wealthy British man named John Harris builds a sprawling estate on the island to use as a summer retreat. Allen said "after 15 years he mysteriously disappears, no one knows where he went, why he went but he just left and the house was there."


Allen told us that in 1838 some people were digging on the island, searching for Captain Kidd's treasure. They supposedly found a box and "were greeted by a headless ghost that chased them off the island." Allen made clear that this story is local lure and there is no documentation to backup the ghost story.

Youtube/Billy Kyle
Youtube/Billy Kyle


A wealthy Waterbury manufacturer named Elizur Pritchard decides to open a resort on Charles Island. Ignoring the stories of the island being cursed, Pritchard carefully landscaped the property and made opulent additions. Pritchard called it "Island House Resort" and it was a success for awhile. Seven years after opening the resort, Pritchard died of a heart attack while crossing the tombola. A tombolo is a sand or gravel bar connecting an island with the mainland or another island.


Susan Pritchard, Elizur's daughter takes over the "Island House Resort." According to Allen, things were running smoothly until after the Civil War. It is right around this time period when business falls off dramatically and Susan is forced to close up shop. The resort's life span was less than 15 years.


A prize fight was to be held on the island featuring Ed Tooley, a marquee name in boxing during this period. Tooley was supposed to fight for the Lightweight Championship of the World but things did not go as planned. Tooley's boat capsized while en route to the island. Tooley was rescued and he survived but the fight went on without him. Organizers replaced Tooley's fight with another bout and when the fight did not meet the standards of the crowd, they rioted. Allen told us "the Governor had to put out the militia, the National Guard at the time and they had actual soldiers come down. New Haven sent 200 police officers and they were all lined up where the tombolo comes on shore. They arrested all of them when they came off."


The Dominican Brothers put a summer retreat on Charles Island. During construction, six workers drowned on Easter Sunday. The retreat closed after six years.

Youtube/Billy Kyle
Youtube/Billy Kyle


A hurricane destroyed all the of structures left behind by the Dominican Brothers.


Two boys walking on the tombolo were swept away by the current. The boys drowned and died.

After all of the calamitous events at Charles Island, the State of Connecticut purchased it and made it part of Silver Sands State Park. Since the state has owned the island, there have been 10 rescues per year of near drowning or drownings. 


A man 34 year old from Hamden man was walking on the tombolo with his 9 year old son when the current grabbed hold of them both. The young boy was rescued but the father lost his life.


A 28 year old man from Bridgeport was walking on the tombolo with his friend when they were dragged in by the current. One of the men was rescued the other drowned and died.

Youtube/Billy Kyle
Youtube/Billy Kyle

If you follow the detailed timeline, going all the way back you'll notice none of the businesses or residences survived past the 15 year mark.

Mike Allen
Mike Allen

Mike Allen also told us he has visited Charles Island and he did walk the tombolo. He made that trip prior to researching the topic and you have to wonder, would he walk the tombolo again, knowing what he knows now?

Captain Kidd was not the only person to put a curse on the island. You can hear the entire story below in our complete segment of "The Place You Live."

Don't forget to check out Mike Allen's Podcast, "Amazing Takes From On and Off Connecticut's Beaten Path" on Apple or wherever you get your podcasts.

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