New Call-to-action
Outdoor Activities

The Thrice Cursed Island: A History of Charles Island

Charles Island
Written by Nikki Pretter

If you’re looking for adventure in CT, look no further than Charles Island. With pirates, curses, and a vanishing road, it’s got everything a good mystery needs!


Charles Island in the Long Island Sound has been a family favorite for generations. Accessible via a sandbar at low tide, it carries with it a certain air of mystery and magic that has long appealed to kids (and kids-at-heart!). But did you know that the island’s history may well have some pirates in it?

The Story

The English settled the Milford area around 1640, and from that point until 1657 the island was known as Milford Island (makes enough sense). It was bought in 1657 by Charles Deal, giving it the name that stands to this day.

According to legend, the infamous pirate Captain William Kidd came to Milford in 1699 before going to Boston, where he was then arrested and sent to England for a trial and execution.

It is said that he buried much of his treasure at Gardiners Island in the Long Island Sound, but it is also believed that he hid some of his riches on Charles Island when he visited the area in 1699. The legends say that it is located under a boulder known to locals as Hog Rock on the island; but after more than 300 years, nothing has been found.

So why is it that people know Charles Island as the “Thrice Cursed Island?” Well, because it was cursed three times. Duh.

The first curse was supposedly places on the island by the Paugussett tribe of Native Americans after they lose the land to European Settlers. The tribe believed that the island was a sacred home to spirits. They cursed any building erected on the island and anyone who would try to inhabit it.

The second curse was placed by Captain Kidd after he hid his valuables before being captured (which was a common practice among pirates). If you curse the land, then you’re going to scare off wannabe treasure hunters who don’t want to deal with zombie pirates.

The third curse was believed to be placed on the island by another group of sailors in the 1700s who, like Kidd, buried their valuables somewhere on it.
Centuries have gone by and, despite the three supposed curses, people still search for the treasures that the island is said to hold. To this day no one has been able to find any of the loot.

About Charles Island

Charles Island is 14-acre island located right off the coast of Milford. The island is so close to the shore that it is accessible by sandbar when the tide is low. Even if the tide is high, it’s easy enough to swim to; many people like to paddleboard or kayak out to it.

Many people make their way out to the island (whether by foot, boat, or fin) each day, especially during the summer. And it’s easy to see why: The island is beautiful (regardless of its claims of pirate treasure) ad offer a unique look back at the mainland of Connecticut, which young kids tend to get a kick out of.

The sandbar is also a unique way of teaching children about the tides. Take them out to the island and back, and wait around long enough for the water to wash over the sandbar: Your kids will be amazed by the disappearing road, which will seem like it was taken straight out of an Indiana Jones movie.

Though the public is free to trek out to the island and enjoy the views, much of the island is today off limits. No, not because of any treasure—but because much of the grounds are now a part of a nature preserve owned by the State. These grounds serve as the breeding and nesting grounds of a number of local endangered birds, so it’s important not to go traipsing through the underbrush (where you might step on an egg!).

If You Want to Go

If you’re in the mood for an adventure, just head to Silver Sands State Park to find your way out to Charles Island. The park is open daily from 8am to sunset. The island itself is only accessible when the tide is low, so plan your trip accordingly: You don’t want to get stuck out there when the tide comes back in!

About the author

Nikki Pretter

Leave a Comment