Connecticut Water Trails Program

Connecticut Coastal Paddling

New Haven County

Milford

Charles Island

Site Location:  Milford, Connecticut

Basic Information:

Charles Island is a 14 acre (57,000 m²) island located roughly 0.5 mile (1 km) off the coast of Fort Trumbull - Milford, Connecticut, in the Long Island Sound.

Charles Island comprises some fourteen acres and is located in Long Island Sound off the coast of Milford, Connecticut. It is accessible from shore via a tombolo (locally referred to as a sandbar), which is exposed at low tide.

According to early local histories, the Sachem Ansantawae resided there during the summer months. European discovery of the island occurred in 1614 when Adriaen Block sailed through and mapped Long Island Sound. The island appears on his hand-drawn map found in The Netherlands National Archives.

The island was also at one time the home to a monastery. Unfortunately a strong hurricane hit the island which destroyed the building and washed most of it out to sea.

Though an island during high tide, during low tide it is accessible by foot using a rocky tombolo that stretches from the beach to the island. Visitors are cautioned about the strong undertow and twice-daily flooding of the sandbar as a result of the tides. Currently (2005) the crossing window is at least two hours. However, Milford locals note that earlier in the 20th century the window was much greater, but erosion has reduced the size and width of the island and sandbar.

Type: Island

Water Type: Freshwater / Saltwater

Season:

Site Contact Information:

Site Coordinates:

Longitude 73.054828 ºW  Latitude 41.190931 ºN

Site History:

After the Milford area was settled by the English in 1639 the island was referred to as Milford Island. No one has successfully lived on the island for any length of time since Ansantawae, chief of the local Paugussett tribe, used the island as his family's summer vacation spot prior to 1639. That was the year he sold it to the early settlers in exchange for six coats, 10 blankets, one kettle, 12 hatchets, 12 hoes, 24 knives and 12 small mirrors.  After Charles Deal bought the island in 1657 it became known as Charles Island. Deal made a failed attempt to raise tobacco on the island – one of the first such efforts in Connecticut.

Over the years, a succession of enterprises were begun and abandoned. Dreams of a tobacco plantation by Charles Deal in 1657 did not come to fruition. The plant that produced fertilizer from dead fish failed to flourish. A hotel was started in the 1880's, but eventually closed. Finally a retreat for Dominican priests from New Haven was tried and subsequently given up. The nickname "Hard Luck Island" evolved as a result of these ill-fated enterprises.

Local records indicate that Captain William Kidd visited Milford in 1699 when he was en route to Boston (where he was subsequently arrested for piracy and murder). Before Kidd’s arrival in Boston, he off-loaded and buried treasure on Gardiners Island off the eastern tip of Long Island. The treasure was retrieved after his arrest but questions remain as to whether all the treasure was in that cache and whether he may have buried more of it along Long Island Sound. Since it is known he visited Milford on his last voyage, it has been speculated that he may have buried some of his treasure on the mainland or on Charles Island.

In 1835, the first permanent residence was constructed on the island by John Harris. After his death the island was owned by several different owners and in 1852 it was purchased by Elizur Pritchard of Waterbury, Connecticut who turned the large house into a summer resort known originally as Charles Island House and later as Ansantawae House.

After the Civil War the resort closed and the island was leased to the George Miles Company as a base for their fish fertilizer operations. After the Miles Company left the island it was relatively unused until the 1930s when the Dominican Order opened a religious retreat on the island. The Aquinas Retreat consisted of a chapel, small cabins for the retreatants, a central dining hall and religious shrines located along paths throughout the island. The retreat closed in the late 1930s and some remnants of it remain on the island.

The State of Connecticut now owns the island and it is part of Silver Sands State Park. It is designated a Natural Area Preserve for the local bird population of herons and egrets. White-tail deer are common as well. The waters around the island have bluefish, snapper blues, sand sharks, and horseshoe crabs.

A Cursed Island

The island was allegedly cursed three times. The first curse was brought in the late 17th century by an Native American chief in response to his daughter's kidnapping, whose tribe fought for the island which they felt was sacred--and "spirited"--ground. The Wepawaug Indians regarded the island as sacred ground.  After the settlers defeated the Indians, the chief proclaimed, "Any shelter will crumble to the Earth, and he shall be cursed." Some feel this is the reason why no building has ever lasted on the island for more than a short period of time.

The second curse was supposedly brought by Captain Kidd in 1699 when he allegedly buried some of his treasure there. The iron chests were filled with gems and gold. Captain Kidd cursed anyone who attempted to dig up his treasure with certain death.

The third curse was supposedly brought in 1721 by five sailors who stole Mexican emperor Guatmozin's treasure from a cave and brought it back to Milford, Connecticut. Guatmozin proclaimed a curse on the stolen treasure. After four of the five sailors suffered terrible tragic deaths, the last sailor hid the treasure in the basement of the old Milford Inn. After it was accidentally discovered by a drunken customer searching the cellar for beer, the remaining fifth sailor rowed out to the island and transported it to Charles Island in the dead of night and buried the booty, bringing the third curse along with him thereby imposing the last mighty curse upon the already beleaguered island

No one has ever found any of the treasures buried on the island, but local legend says that two treasure hunters came very close in 1850. They found an iron chest that was buried at the island. As they attempted to open it, a "screeching, flaming skeleton descended from the sky". It lurched into the pit where the treasure lay, sending forth a shower of blue flames. The treasure hunters were so terrified that they dropped their tools and fled the island. The following day, the two returned to the island only to find that their tools were gone and the digging site had been smoothly covered up, as if they had never even been there. Some say that the two men spent the rest of their lives in an insane asylum while others say that they were beheaded by the spirits of the Paugussett Indians, who made the treasure invisible.

Many people who have visited the island in recent years have reported seeing glowing ghosts in trees and hearing the sounds of disembodied voices and music of festivities from the past. Some think that the ghosts may even be phantom monks, who continue to make their processionals through the monastery ruins.

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