The Legend of Dudleytown
The article that Dark Entry Forest, Inc. doesn't want you to read

By Robert Winkler
About the Author

A note on free speech
Dark Entry Forest, Inc. tried to suppress publication of this article—both on the Web and in my new book, Going Wild: Adventures with Birds in the Suburban Wilderness (National Geographic). They failed. This article is dedicated to all who cherish and defend the exercise of free speech. —Robert Winkler, July 4, 2004

he remnants of Dudleytown lie on a hill in northwest Connecticut, near the village of Cornwall Bridge. Settled in the mid-1700s, Dudleytown was all but abandoned by the early 1900s. Today, stone foundations and cellar holes, surrounded by New England’s ubiquitous stone walls, stand as solemn memorials to the small, troubled community that once existed there.

Rocky soil and cold winters—banes of the New England farmer—have been blamed for Dudleytown’s demise. But a legend has grown up with the thick forest that now covers the once-pastoral landscape: from the start, Dudleytown was cursed.

The curse has been traced to an English nobleman, ancestor of the Dudley brothers who settled the town. Back in England, old Edmund Dudley got his head chopped off for plotting against King Henry VII. Someone or something put a curse on Edmund that followed his family to the New World and took root in Dudleytown.

How else explain the disproportionate number of horrors that befell tiny Dudleytown’s residents? According to some local historians, the town’s stony remains have witnessed madness, suicide, fatal accidents, natural disasters, and vanishings.

In what is often cited as the first manifestation of the curse, one of the Dudley brothers went insane. Other strange incidents: At a barn raising, a man fell to his death (or was it murder?). Lightning struck and killed a Dudleytown wife, right on her porch. A sheepherder watched helplessly as the curse destroyed his family. His wife died of tuberculosis, and his children disappeared. When his house burned down, he wandered into the woods, never to return.

According to the chroniclers of Dudleytown, New York Tribune editor Horace Greeley should have followed his own advice (“Go West, young man”), and taken his wife. They claim that Mrs. Greeley, better known as Mary Cheney, hanged herself in Dudleytown in 1872.

It should be noted that Rev. Gary P. Dudley, a Texas resident and the author of The Legend of Dudleytown: Solving Legends through Genealogical and Historical Research (Heritage Books, 2001), disputes the foregoing. In tracing the genealogy of his name, he found virtually no historical basis for Dudleytown’s cursed reputation—no genealogical link to Edmund Dudley, no mysterious illnesses or deaths. As for Mary Cheney, he says she never set foot in Dudleytown.

By most accounts, including Rev. Dudley’s, the final resident of Dudleytown seems to have been Dr. William Clarke, a New York City physician. Dr. Clarke built a vacation home in Dudleytown in the early 1900s; Mrs. Clarke was yet another wife visited by tragedy.

The traditional story places her in Dudleytown at the time. While her husband attended to an emergency in the city, leaving her alone overnight, she descended into madness. But as Rev. Dudley’s tells it, Mrs. Clarke committed suicide—in New York, not in Dudleytown.

Before moving out of Dudleytown, Dr. Clarke founded Dark Entry Forest, Inc., an association of property owners that designated Dudleytown a nature preserve. As Dudleytown fell to ruin, the land reverted to forest.

The locals avoid Dudleytown, and according to legend, so do wild animals. Except for the owls. In the ever-present darkness that shrouds Dudleytown Hill, owls are said to hoot throughout the day. Hence Dudleytown’s nickname: Owlsbury.

One soggy afternoon in mid-October, I decided to investigate Dudleytown. Following directions in a guide to nature walks in Connecticut, I drove with a slightly reluctant companion to the 750-acre preserve’s main entrance at the end of Bald Mountain Road in Cornwall. There, we saw something frightful indeed: a slew of No Parking and No Trespassing signs in front of a locked gate.

As we assessed the situation, an SUV came barreling down a nearby driveway. Out jumped a woman who warned that if we dared park there, someone would photograph my car and call the police. Before disappearing down the street, she raised the specter of towing, fines, and arrest.

When we got over the shock, I took out my maps and saw that we could enter Dudleytown from the Mohawk Trail, a bit farther north. From there, it's a 1.5-mile hike to Dudleytown, but with our false start, we wouldn’t get there until after dark. I wanted to experience Dudleytown at night, but I’d planned to see it in daylight as well. We agreed to return the following weekend.

Meantime, I did some digging and learned why Dudleytown’s neighbors don’t cotton to strangers. The legend has long attracted paranormal investigators, journalists, hikers, the occasional birder, curiosity seekers, and just plain folk inclined toward the supernatural. But in 1999, after the release of “The Blair Witch Project” (the hugely popular movie about haunted woods in Maryland), goings on at Dudleytown got out of hand. Web sites, meanwhile, were spreading the legend far beyond its traditional word-of-mouth audience.

Complaining of drinking parties, campfires, littering, disorderly conduct, and vandalism, the members of Dark Entry Forest, Inc. placed Dudleytown off limits. A press release they sent to local papers noted that, in a single year, police had been called to the area 79 times.

One case involved five teenagers who got lost in Dudleytown at 1:30 a.m. They used a cell phone to call 911, and the police dispatched a search team that included state troopers, firefighters, dogs, and a helicopter. While conducting their rescue, the team scared up a second, separate group of six teenagers. Each trespasser was fined $77.

Such high jinks explain why a sign in the Mohawk Trail parking lot warns hikers to keep out from October 25 to November 4. The trail crosses Dark Entry Forest, Inc. land, including a corner of Dudleytown. In deference to the neighbors, The Connecticut Forest and Park Association closes this leg of the trail for several days on either side of Halloween.

We pulled into the lot on the afternoon of October 20. It was sunny and cool, and come evening, we’d see a nearly full moon. Driving north on Route 7, I had marveled at the fabled Litchfield Hills in their autumn colors and at the crowds of tourists on Main Street in Kent.

The blue blazes of the Mohawk Trail follow Dark Entry Road, which climbs steeply and passes several houses and many towering trees—including one with a bulging, fistlike trunk—before narrowing into an uphill path that hugs Bonney Brook. As we trudged along the road, golden-crowned kinglets flitted about the treetops, their energetic three-note calls punctuating our breathless conversation.

We saw a myrtle warbler and two or three hermit thrushes; heard a pileated woodpecker, chickadees, titmice, and nuthatches. The birds gave no signal that we should abort our mission.

After plunging into the forest, we passed a huge fallen hemlock rotting away on the opposite bank of Bonney Brook, its red carcass folded over blackish rocks. Soon we reached a broken stone wall that crosses the brook. Once it had been a dam—Witches’ Dam, some now call it. Nearby, we heard a hollow moaning that we traced to a thin stream of water spouting into a rocky pool.

A half-mile beyond, we crossed the brook and entered Dudleytown, which the trail guide of The Connecticut Forest and Park Association refers to only as “an abandoned community.” By then, we were far from major roads. It was so quiet we spoke in hushed tones as we poked around the doomed settlement’s stone ruins. Yet we still heard kinglets.

We weren’t alone: loud voices, startling in the sylvan silence, preceded the appearance of two young couples. I think we gave them a start, too, standing there calmly as they came around a turn in the trail.

They expressed interest in spirits, and noticing my binoculars, asked if I had seen any birds. They found it hard to believe I had, even after I pointed out a hairy woodpecker over their shoulders. Apparently they subscribed to the “wild animals shun Dudleytown” part of the legend. Intent on getting out of Dudleytown before dark, they moved on.

Although the trail closes at sunset, we stretched the rules and stayed until dark to get the full effect. Some have experienced vortexes and cold spots in Dudleytown. Others have seen apparitions or recorded them on film (though cameras and other battery-powered equipment don’t always work there). A few claim to have been chased, even slapped, by ghosts. My companion and I cannot count ourselves among the chosen few.

Still, I was impressed that Dudleytown lived up to its nickname. We did hear owls in Owlsbury—a late-afternoon love duet performed by male and female barred owls. Almost simultaneously, we heard the croaks of two common ravens—Edgar Allan Poe’s “ghastly grim and ancient” wanderers. They passed directly over us, cackling to each other as they flew to night’s Plutonian shore.

On the way out, we made some wrong turns but never strayed far from the trail—with a little backtracking, we picked it up again. Flying squirrels squeaked in the moonlight; a Canada goose honked. I pretended that the blue trail blazes painted on the trees had turned scarlet and dripping wet in the darkness. “Shut up,” said my companion.

We heard distant wailing—maybe a coyote—and in the gloom of Dark Entry Road, my companion almost stepped on a junco, which had been lying on its side. It fluttered up and disappeared into hemlock saplings. Had it become intoxicated from feasting on fermented berries? Was it a tired migrant? Or had it succumbed to Dudleytown’s spell?

Whether Dudleytown is haunted, I can’t say. I do know I’ll be returning to walk along its stone walls, to climb nearby Echo Rock and Coltsfoot Mountain, and to stand among the tall trees of Dark Entry Forest. If the psychic static emanating from gatekeepers and gatecrashers isn’t too intense, who knows what I’ll find?