Legend holds that Dudleytown is the earthly receptical of a curse that began in 1510, when Edmund Dudley was beheaded after he was revealed to be conspiring to overthrow the King of England. His son, John Dudley, tried to marry his son to Lady Jane Grey, thus entering the royal family...and all three were executed. Shortly afterwards, John Dudley's other son returned from France, bringing the plague with him and unleashing an outbreak that killed thousands of people. John Dudley's third son decided to get out while the gettin' was good and left for the Americas in 1630. Once there, he had sons, who would later settle in Connecticut...
Or, an alternate version is that Governor Thomas Dudley of the Massachusetts Bay Company was related to Edmund Dudley, and was the uncle of four Dudley Brothers who settled in Connecticut. In this version of the story, Thomas Dudley is a horrible tyrant who executes those who are not Puritans...
But regardless of the exact version, four brothers, Abijah, Barzillai, and Abiel, founded Dudleytown in the late 17th or early 18th century. Depending on which version of the story you are going with, these four brothers carried a curse with them, or one of Thomas Dudley's victims cursed him and all who dwellt near him (including his nephews), damning the land on which he lived, which would become Dudleytown. In the Governor Dudley version of the story, he is murdered - hacked to death and his body left on his land - and the murderer is never found.
The three Dudley borthers lived the rest of their lives in Dudleytown, Abijah and Barzillai dying of natural causes, apparently. But Abiel...oh, Abiel went insane! He lost his mind, and shorlty afterwards lost his fortune and even his home, dying a pauper
While Abiel was still alive, Nathaniel Carter bought Abiel's house (the unfortunate fellow could no longer afford it) in 1759, thus activating the curse*. After displacing poor, mad Abiel, the Carter family moved out of Dudleytown in 1763 and went to reside in Bimghamton, New York...but somehow left their 13 year old son behind. The result, rather unexpectedly, was that the son survived the rest of the family when a Native American raiding party attacked the Carter's New York homestead in 1764, gruesomely killing and scalping Nathaniel Carter, his wife, and even their infant child. In 1774, Nathaniel's borther, Adoniram, and his entire family died of cholera, thus adding more lives to the Dudleytown curse.
And the horror kept on coming. In 1792, Gershon Hollister is said to have been murdered at the home of William Tanner. Afterwards, Tanner reported seeing strange animals in the forest as well as demons, and this eventually drove him insane. In 1804, a General by the name of Swift was at home with his wife, when she walked out to the front porch and was killed after being struck by a bolt of lightning. Mary Cheney was born in Dudleytown in 1811...and the curse followed her after she left, leading to disaster in her hsuband's career and sickness on her part, and she finally committed suicide in the 1830s. An unspecified plague hit the town in 1813, killing all of one family (the Jones family) and killing off many others.
As the 19th century wore on, crops failed, farm animals routinely vanished without explanation, and unexplained deaths continued. Come the end of the 19th century, only the Brophy family (transplants from elsewhere who arrived in 1892) remained. First the Brophy sheep began vanishing, then his sons vanished (though it is worth noting that they were wanted by local law enforcement...so, "on the lam" might be a better description than "vanished"). After a few years, Mrs. Brophy died of unknown causes. He was sometimes seen around Cornwall, muttering about "demons"...and then his house burned to the ground and he vanished, as well.
Dudleytown remained abandoned to whatever demons Mr. Brophy had encountered until 1930, when Dr. William Clark, a pathologist from New York, decided to build a summer home at that location. Things were quiet until 1937, when Dr. Clark left on a business trip, leaving his wife behind. When he returned home, he found her in an upstairs room, cackling to herself, having gone quite mad. She never recovered, eventually dying in an asylum.
Dr. Clark was the last resident, but the Clarks weren't the last people to encounter evil at Dudleytown. Local folklore tells of a satanic biker gang that enters the Dudleytown area to hold rituals. People report being attacked by demonic creatures with cloven hoofs and strange green eyes. People report seeing shadow people, floating balls of light, dark human forms rising out of the cellar pits, having weird images show up on film (or in digital pictures), and that animals seem to be strangely absent from the area. And, as is so often the case, stories persist that a TV news crew arrived to film a story around Halloween, only to have their equipment fail while they were present.
*For the life of me, I can not figure out why the curse is said to begin with one of the Dudley ancestors...when A) they weren't actually related, and B) the alleged displacement of an unfortunate madman seems to be reason enough to cause the curse without the convoluted stuff from the previous centuries.
Commentary: As ghost stories go, this is one of the greats. Dudleytown is creepy, famous, and a real place...all of which make for a good story. The story of the curse, the demonic creatures having been sighted by residents, and the fact that the ruins are still there (though entry is prohibited by the current landowners, and people do get arrested for trespassing, so, really, stay out), it all makes this particular tale all the more delicious as ghost stories go.
Unfortunately, for all of the giddy creepy thrill that the story supplies, it really doesn't stand up to any sort of scrutiny. As at least one source has pointed out, the story of the curse and the early deaths/madness actually doesn't hold up very well, even using just the information provided in the common versions of the story itself - pretty much everyone who is said to have died or been driven insane by the curse was quite elderly at the time...and, well, therefore would be expected to be experiencing dementia or death (for example, Abiel was 90, and the symptoms of his madness are pretty consistent with dementia). Moreover, the number of people who are said to have died in various versions of the stories are, actually, well short of what you would expect for a rural 18th/19th century community, indicating that being in Dudleytown might actually have been good for your health. So, ya'know, not so scary, that.
A short but accurate and useful write-up of Dudleytown's history if provided on it's Wikipedia entry (accessed October 23, 2013):
Dudleytown was never an actual town. The name was given at an unknown date to a portion of Cornwall that included several members of the Dudley family. The area that became known as Dudleytown was settled in the early 1740s by Thomas Griffis, followed by Gideon Dudley and, by 1753, Barzillai Dudley and Abiel Dudley; Martin Dudley joined them a few years later. Other families also settled there.
As with every other part of Cornwall, Dudleytown was converted from forest to farm land. Families tilled the land for generations. Located on top of a high hill, Dudleytown was not ideally suited for farming. When more fertile and spacious land opened up in the mid-West in the late 19th century, and as the local iron industry wound down, Cornwall's population declined.
During the early 20th century, old farms in Cornwall were sold to New Yorkers seeking a better life in the countryside. Much of the Dudleytown area land was acquired by the Dark Entry Forest Association, which planted thousands of trees. During the 1930s, New York's Skidreiverein Club spent their winter weekends skiing on trails they built in Dudleytown; in the summers, they canoed down the Housatonic River.
Then, even the mysterious or horrifying deaths turn out to be more mundane than legend would hold. Records show that Gershon Hollister was not, in fact, murdered, but instead died due to an accident during a barn raising. Mary Cheney did not kill herself, but died of a lung disease, likely tuberculosis, and she had never been to Dudleytown - her death is especially easy to trace, as she married Horace Greeley. Harriet Clarke did commit suicide, but in New York, not Dudleytown. General Swift lived in another location near, but outside of, Dudleytown (also, Swift was, like Abiel, quite elderly when he "went mad" so it was probably just dementia again). Mrs. Clark was not driven insane, and in fact continued to live in the area after her husband's death in 1943. And so on and so forth...
What's more, the verifiable history of Dudleytown is rather different than the legend holds. There's no known relation between the Dudleys of Connecticut and Edmund Dudley. Similarly, if you match up the time the periods during which the Dudleys of Dudleytown lived (the mid-to-late 18th century) with the life of Thomas Dudley...that he was their uncle seems remarkably unlikely...and they didn't settle in the area until after others already had, so their uncle would not have lived there, and in fact he died of natural causes at his home in Roxbury in 1653. Also, the Dudley brothers were actually Gideon, Barzillai, and Abiel, there wasn't an Abijah.
What's more, there is plenty of evidence that the town was deserted not because of weird supernatural goings-on, but because of the difficulty in obtaining freshwater, poor conditions for agriculture (rocky ground and a placement that resulted in shade from the hills and trees pretty much all the damned time), and variations in the local iron industry all provided potential causes for abandonment. Add to this that Dudleytown was never really a town (stories of it having been a more substantial settlement are false), but rather part of Cornwall, and, well, many residents probably just moved to other parts of the town or county when land became available.
One Reverend Dudley, the author of the Legend of Dudleytown page linked to below, traces the origin of the ghost stories to the 1938 publication of the book They Found a Way, though it is conceivable that elements of the story already existed in local folklore, but even that isn't too terribly odd a thought. After all, frequently shadowy location with an abandoned town? If you don't make up a ghost story for that, then you are just being a lazy sod.
Still, even knowing all of this, I still love this story. It still creeps me out, and if I ever find out that I will be visiting Connecticut, I will try to get permission to visit this site.
Sources: Wikipedia, The Legend of Dudleytown, Cornwall Historic Society, Prairie Ghosts, Ghostvillage, Damned Connecticut, ghosttowns.com (wildly inaccurate information, but a fun read), The Illustrious Internet!, The Ghosts Of Ohio (because, of course, a website about Ohio will cover Connecticut), Exciting Earth, paranoid ramblings from the Illustrious Internet