By THOMAS D’AGOSTINO

A deserted settlement deep in the woods of western Connecticut has been the subject of writings, short stories and even movies. Owlsbury was once the more common name for what we today call Dudleytown. The abandoned settlement is said to harbor demons, evil spirits, negative energy, and a host of other foreboding horrors that have caused people to either shun the area, or at present, risk being arrested while searching for the now forbidden ghost town. There are many narratives regarding the area and the negative energy that abounds within. Many have sworn to the old tales while others brush them off as legends created to scare the meek.

Dudleytown is nestled on a plateau in the middle of three mountains and a hill. The original owner, Thomas Griffis, took deed to the area in 1738. Abiel and Barzillai Dudley, both soldiers in the French and Indian War, took title to a parcel of land in 1747, “on the road from the meeting house to Mr. Griffis.” This would soon become known as Dudleytown. The Dudley family was said to have brought a family curse over from England where several of their ancestors were executed for various plots against the government.

At one point thirty-five families called Dudleytown their home. Names like Carter, Jones, Tanner, Dibble, Rogers and others unknowingly made history by settling in the small town. The chief product was charcoal, for the area was heavily wooded. 

It cannot be precisely discerned when the horror stories about Dudleytown began to circulate. The 1938 Federal Writer’s Project book on Connecticut gives the abandoned village but a small paragraph within its pages and not much more. It mentions the trail where hikers traverse to “the dead end and mystery of Dark Entry...no other road, other than a pack horse trail ever penetrated this forbidding region.”

The writer continues;

“Tradition tells of a man, who with his wife, built a cabin in this wilderness. After an absence of two days, in which he tramped to the village for supplies, he returned to find his wife a raving maniac, driven mad by some terrifying experience which she was never able to relate.” 

The narrative most likely concerns Dr. William Clarke and his wife. The doctor bought a piece of land in Dudleytown and built a cabin as a summer retreat. He became one of the founders of the Dark Entry Forest Association, a group of people who bought land in and around Dudleytown to preserve the former settlement and woods around it. The entry in the book also states that there are graves deep in the woods of those who have gone in and died of starvation or an accident. The writer refers to the place as Dark Entry or Owlsbury but never once mentions it as Dudleytown. The term Dark Entry referred to a forty foot tunnel that ran from the road to the cellar of a home. Unfortunately, both are long gone but the name has stayed on, creating ominous visions for those who read of the lost town.

One very famous account is that of Richard Brophy, the last inhabitant of Dudleytown. Brophy left his land in 1901 after his house burned to the ground. Before that, his sons disappeared after they were caught stealing sleigh robes, and his wife died of consumption shortly after. It is alleged that the man showed up at the local tavern half insane and jabbering about half man-half animal cloven hoof beasts chasing him off his property. After that, he was never heard from again.

People suffered strange calamities while living in the cursed village. One of the Dudley brothers was found hacked to death near his home, another mysteriously fell from a ladder, one more died while visiting a neighbor’s home. These and many more were attributed to the curse and the demons, both visible and invisible that were said to inhabit the land.

Tales of people going insane ran rampant. Abiel Dudley was one of those who went mad, but he also was about ninety years old when he was considered feeble of mind. William Tanner was another Dudleytowner who was considered to have become feeble-minded. He lived to be one hundred and four years old. Several other accounts tell of Dudleytowners going mad after witnessing what they called wild half human beasts. Dr. William Clarke’s wife was another as previously stated, but records indicate she died in a New York hospital from a physical illness.

Part II next month.