The Many Mysteries of Rogues Hollow Road

A headless horse is among the phantoms said to haunt this formerly rough-and-tumble holler near Doylestown, Ohio.

• Rogues Hollow was a nineteenth century mining community known for its rambunctious residents.
• According to legend, a low-hanging branch decapitated a horse along the trail, and its spirit returns.
• The bridge over Silver Creek is one of Ohio’s many “crybaby bridges.”

Rogues Hollow is a geologic depression and former town located south of the village of Doylestown in northeastern Ohio, a few miles southwest of Akron. Though long defunct, the road and bridge of the same name has long been a magnet for legends. Today, Doylestown celebrates its unique heritage with the Rogues’ Hollow Festival, an annual event which takes place the first Friday and Saturday of August.

Though one of many “crybaby bridges” scattered throughout rural Ohio, Rogues Hollow’s notorious history makes it unique. Rogues Hollow was formed after centuries of erosion by the meandering of Silver Creek, and the area was settled in the early 1800s when coal deposits were discovered. In 1958, Russell Frey printed a collection  of area history called Rogue’s Hollow: History and Legends. He described the mining community as rough-and-tumble, full of taverns, violent episodes, and tormented spirits.

One old legend is of the Chidester Mill ghost. The ghost was believed to belong to a mill worker who fell into the wheel and was crushed to death beneath the churning waves. The ghost guarded the area jealously, and supposedly started a fire in the Chidester House because an outsider expressed interest in purchasing it.

According to Frey, the legend most associated with Rogues Hollow was not a crybaby bridge, but a headless horse. The Ghost Oak Tree once stood at the top of a hill near Route 65. One branch hung so low, riders had to duck to avoid being smacked in the head as they passed.

According to legend, one unfortunate horse ran into the branch (weighted down by ice) at full speed, and it severed the animal’s head. From then on, riders reportedly saw a devil or impish creature sitting on the headless horse beneath the tree.

A more modern legend is the crybaby bridge. At the bottom of the hollow, a bridge crosses Silver Creek. According to legend, a car traveling across the bridge slid on ice and plunged into the creek. Its occupants were killed instantly, but their baby was stranded in the car and slowly starved to death. Today, it’s cries can be heard in the surrounding woods. Other variations on the tale claim a woman threw her newborn baby off the bridge.

More ghost stories circulate about the old foundations and mines of Rogues Hollow. Eyewitnesses report seeing the gray, whispy figure of a woman in a frontier dress, and hearing an old train. Today, Rogues Hollow is a park and historic site maintained by the Chippewa-Rogues Hollow Historical Society. The park is closed at night, but visitors can enjoy this unique piece of history during the day.