Tucked up in the hills of northwestern Connecticut is a ghost town called Dudleytown. Settled in the eighteenth-century the hamlet’s history is rife with stories of Indian massacres, murder, suicide, fatal accidents, disappearances, and insanity. So much mysterious calamity plagued Dudleytown—also nicknamed Dark Entry—that by the nineteenth-century the settlement had been abandoned. Today, all that remains of Dudleytown are crumbling stone walls, cellar holes and a few foundations, all hidden in the deep, dark woods.
Some people think that Dudleytown’s trials and tribulations could be directly tied to a curse that followed the Dudley family. Before any Dudleys came to America, two of them had already lost their heads to the executioner’s axe in Merry Old England. Edmund Dudley was executed in 1510 for supporting a plot to overthrow King Henry VIII—who seemed to be quite fond of beheading people. Like father, like son, as John, Edmund’s son, also went to the chopping block years later for again trying to overthrow the crown. Finally getting the message, John Dudley’s son Robert fled England. Eventually, the Dudleys arrived in America. Joseph Dudley was born in Saybrook, Connecticut in 1674 and it was three of his sons that brought property in the hills of Cornwall that became known as Dudleytown.
Other settlers followed the Dudleys into the woods and it wasn’t long before tragedies began falling upon them like autumn leaves. Some Dudleytown residents died at the hands of Indians during the French and Indian War. In 1774, an epidemic wiped out an entire family named Carter. Another Carter family, relatives, moved to upstate New York, devastated by the loss of their kin. There, Indians tomahawked to death the head of the family, Nathaniel Carter, as well as his wife and infant; the Indians kidnapped the other three Carter children and brought them to Canada.
In 1804, a Revolutionary War veteran, General Herman Swift, went insane when lightning struck and killed his wife Sarah as she stood on their front porch. In 1872, Mary Cheney, the wife of the famous journalist Horace Greely, killed herself; she had been born in Dudleytown.
Toward the end of the nineteenth-century few residents remained in Dudleytown, but the curse of the Dudleys was still at work. After John Brophy’s wife died of consumption (tuberculosis), his two children disappeared into the woods. Brophy then set fire to his house, burning it to the ground, and walked away from Dudleytown; he was never heard from again.
In 1920, Dr.William Clark from New York City built a summer home in the now abandoned Dudleytown. With some friends he established the Dark Entry Forest Association with the intent of maintaining the former settlement and woods as a nature preserve. A few years later, Dr. Clark was called to the city on an emergency, leaving his wife alone at their house in Dudleytown. When he returned home, he found his wife cowering in a corner. She had gone insane and spent the rest of her life in a mental asylum. No one knows what happened to her but some people say that “something” from the forest attacked her.
Today, Dudleytown remains part of the Dark Entry preserve. It is private property and trespassers are prosecuted. Yet, the curious continue to sneak into the woods to find evidence of the Dudleytown curse . . . or worse.
Stay tuned to find out what they have discovered.