Wish Sheppard’s Handprint on the Jail Cell Wall

Denton Jail
Denton Jail – now expanded to as Caroline County Jail – Haunted by Wish Sheppard

One of the Eastern Shore’s most famous ghost stories is about the hand-print that Wish Sheppard left on the jail cell wall just before he was pulled from the cell and taken out behind the jail to be hanged in front of hundreds of people.

The Caroline County Jail has been haunted by the ghost of Wish Sheppard since the 1940s – at least the testimony from the Sheriffs and jail wardens say so. Even today when we do our Denton ghost walks, there’s always someone on the walk who either works in the jail or knows someone who does. And they will pour fourth the stories of file cabinets in empty rooms slamming shut, gates blowing in the wind, security alarms going off, furniture rearranging, books and items on shelves dropping like dominoes.

The scariest testimony I every heard was from Warden Charles Andrew who recently retired. He was the son of a Sheriff and the grandson of a Sheriff. Charles has seen the hand-print and he talked about many strange happenings. But the scariest tale Charles told wasn’t about the hand-print. It was when the staff at the 911 dispatching office seeing the red eyes of Wish Sheppard peering through an internal window.

Aloysius “Wish Sheppard”

In July of 1915, Aloysius “Wish” Sheppard was arrested for raping young Mildred Clark of Federalsburg. Later that year, he was convicted and sentenced to death by hanging. Wish Sheppard lived in Federalsburg with his mother and was approximately 19 years old at the time. He confessed to the crime, but later recanted stating he was coerced into confessing – threatened with being released into the hands of an angry mob if he didn’t confess. And the mob was angry.

Originally, the hanging was set to be held inside a barn near the Denton jail and courthouse, with no public witnesses, only a few close to the case. However, the venue was changed to “outdoors” once rumors surfaced about a mob, hungry to watch the rapist hang, intending to burn the barn down the night before the scheduled execution. He was hanged from gallows erected on a slight slope behind the Caroline County Jail in Denton just along the Choptank River.

Hundreds attended the hanging and observed the gory event from the ground, from boats on the river, some even hung from the trees. The event has been memorialized in two commemorative postcards both entitled “The Hanging of Wish Sheppard” – one showing the condemned man on the scaffold and the other showing the scaffold with trap door open and the rope pulled taught with the obvious (though not visible) body at the other end.

Hand Print on the Jail Cell Wall

The hanging of Wish Sheppard in 1915 was the first legal execution in Caroline County in nearly one hundred years … and it was the last.

As the tale goes, Wish Sheppard vehemently resisted his final walk to the gallows. Having one hand gripping the cell bars and the other flatly pressed against the cell wall, the guards had to pry his body out of the jail cell to be marched to the gallows. (This resistant behavior has been refuted by eye witnesses – but it makes a good story.) Regardless of how Wish left his cell, a hand print remained on his cell wall. After the execution there were many attempts to cover over the hand print both with paint and with plaster – but it always resurfaced. Over the years prisoners and guards have reported strange occurrences and spooky incidents attributed to Wish Sheppard haunting the Caroline County Jail in Denton.

Retired Sheriff Louis Andrew (father of Charles mentioned above) has been interviewed numerous times regarding the Wish Sheppard haunting of the jail house in Denton. Sheriff Andrew moved into the Sheriff’s living quarters in the Jail when he was ten years old and his father became the Sheriff for Caroline County. In those days the Sheriff and his family lived at the jail and provided for the prisoners. In 1961, Louis Andrews succeeded his father as Sheriff and though he never saw Wish Sheppard or had any direct contact with paranormal occurrences, he can recount dozens of experiences relayed to him by prisoners and guards at the jail.

The Haunted Jail

Sheriff Andrew has recounted how he tried to paint over the hand print numerous times and it would always eventually resurface through the paint. He even put cement across it once, but the hand print returned. Prisoners would awaken the Sheriff in the early hours of the morning scared to death, saying they saw the ghost of Wish Sheppard or heard footsteps or chains clanking or a shadowy figure walk by. The Sheriff would have to go all around the jail with his flashlight showing the prisoners that no one was there. On one occasion a prisoner claimed the ghost came into his cell and attacked him. The cell door had been locked all evening, and no one else was in the cell. But the prisoner had scratches all over his arms and face. The door to the Wish Sheppard cell would never open easily. The cell wasn’t used.

After Renovations, Torment Shifts

The Jail was remodeled in the early 1980s. According to Sheriff Andrew, during the renovations another wall was erected over the one with the hand print and the jammed door to Wish Sheppard’s cell was simply kept in place and the renovations went on around it. The renovations seemed to bring an end to the torment of prisoners by whatever ghostly presence dogged the Jail. But, the torments were redirected to jail staff and guards. Many workers report seeing the figure of a man in the security monitors. When a guard goes to investigate, there’s no one there. Others report that the elevator will operate by itself in the wee hours of the morning, with no one riding on it. A cold chill has been known to fill the rooms. Footsteps are still heard in the halls and lights still go off and on mysteriously. Most who work in the jail are used to it and say to themselves, “It’s just ol’ Wish Sheppard checking things out.”

Wish Sheppard - just before his execution.
Wish Sheppard – just before his execution.


A photographer captured a rare photo of Wish Sheppard sitting in a chair prior to an interrogation. The photo was printed on postcards and sold in the public market. Few exist today. The image on the post was scanned from an original postcard courtesy of Sonny Callahan who lives in Denton and is an avid post card collector. We sincerely appreciate Sonny’s generosity in allowing us to share an image of his postcard.

Denton Ghost Walk
The Caroline County jail is on the Denton Ghost Walk and the story of Wish Sheppard is told in more detail.