Old Denton Jail

A 19th-century jail on Maryland's Eastern Shore, believed to be haunted by the ghost of executed murderer Wish Sheppard.

The Old Denton Jail, officially the Caroline County Jail and Sheriff's House, is considered the most haunted site on Maryland's Eastern Shore. Built 1906-1907 in Colonial Revival style, the elegant granite structure overlooking the Choptank River was designed as both the Sheriff's residence (first floor) and jail (upper floors). The building's paranormal reputation stems primarily from the ghost of Aloysius "Wish" Sheppard, executed August 26, 1915.

Wish Sheppard was a 19-year-old African American from Federalsburg convicted of assaulting 14-year-old Mildred Clark. He confessed but later recanted, claiming coercion under threat of mob violence. The night before his death, two Black preachers (Rev. J.H. Fitchett and Rev. F.T. Johnson) and four women held religious services in his cell, singing and praying for him. Sheriff James Temple erected wooden fencing to obstruct the public view, but hundreds gathered anyway—on balconies, in boats along the Choptank River—to watch the hanging. A Baltimore photographer captured the execution on commemorative postcards showing Wish on the gallows and his dangling body afterward. His mother claimed Wish and Mildred were friends who "spent time together." County officials helped her claim his body secretly to prevent desecration, burying him in an unmarked grave. This was only the second legal execution in Caroline County history (the first being Shelby Jump in 1829).

The mysterious handprint appeared on Wish's cell wall after the execution. According to legend, he gripped the doorway resisting his final walk, though eyewitnesses dispute this—describing him as calm and composed. Sheriff Charles Andrew tried repeatedly to cover the handprint with paint, plaster, and even cement, but it always bled through. During 1980s renovations, workers simply walled over the original cell rather than destroy it. Years later, kitchen remodelers discovered "a wall behind a wall with a door in the middle"—Wish's original cell door and the indestructible handprint.

The Caroline County Jail has been haunted since the 1940s according to sheriffs and wardens. Staff, inmates, and even the warden call the resident spirit "Shep." Paranormal activity intensified after renovations, shifting from tormenting prisoners to affecting staff.

Control Room incidents are common: guards report phantom footsteps ascending the spiral steel staircase only to find no one there; a black spot once appeared on security monitors, expanded toward the camera, then completely obscured it before vanishing. Officers have witnessed shadows walking hallways and "a man in black with what looked like a top hat."

The most terrifying account came from Warden Charles Andrew: staff in the 911 dispatching office saw the glowing red eyes of Wish Sheppard peering through an internal window.

Other documented phenomena include: file cabinets slamming in empty rooms, security alarms triggering without cause, furniture rearranging overnight, books falling like dominoes from shelves, and the elevator operating independently in early morning hours with no passengers—doors opening to empty cars visible on monitors. Cold rushes of air pierce staff members on stairs and in the booking area with no open doors or windows to explain them. A phantom bell from the secured prison yard rang during evening meetings when no one could access it.

Inmates historically reported chains dragging up and down metal steps at night. One prisoner claimed the ghost attacked him, leaving visible scratches despite locked doors. Another named Annie Thomas complained repeatedly about the chains. Some reported missing watches that later appeared broken outside the jail.

Staff have developed rapport with Shep. One worker calls out "Wish, if that's you, let me know" and receives responsive knocking on pillars. Lieutenant Brown observed: "Shep was treated badly all his life. He's just stuck here, reminding us to be nice to one another." The warden noted: "Shep is just there. He isn't angry or up to something. He just lets us know that he's there." Most activity occurs between 2-3 AM.

The jail sits near the Courthouse Green, site of three documented lynchings: David Thomas (1854), Jim Wilson (1862), and Marshall E. Price (1895)—all extracted from this same jail by mobs. The combined history of legal execution, mob justice, and supernatural phenomena makes the Old Denton Jail one of the most actively haunted locations on the entire Eastern Shore.