My Time in the Denton Jail


The Denton Jail in Caroline County, MD is one of the five most haunted sites on the Eastern Shore – in my opinion. I gauge this by considering the number of haunted stories from unrelated sources spread over many years, and that the site is still active today.

The jail was built in 1906 . The old part of the building looks  a little like a house with a front door and porch. It was a house of sorts because the Sheriff lived there with his family when the jail was built. They lived on the first floor and inmates were housed in other parts of the building. The Sheriff’s wife attended to the inmates’ needs for food, laundry, etc. The jail is an active county correctional facility and has gone  major renovations in the last 109 years. It’s gone from one Sheriff with no deputies and a handful of inmates to a correctional facility with room for 150 inmates.

My Tour of the Denton Jail

A few weeks ago, I was cleared by the Warden to get a tour of the jail to help with my research, and to also have the opportunity to interview several of the staff who had worked there for many years.  The topic of our interviews?  The ghost of Wish Sheppard, who is believed to haunt the jail.  In fact, he’s haunted it for one hundred years, messing reaching out to inmates and staff.  It was a thrilling two hours for me. Seeing the inside of that jail was amazingly helpful, but just as helpful was the time spent with staff members hearing them recount their experiences.

“Wish Sheppard” (full story here) was executed on August 26, 1915. It was one of two legal executions in Caroline County – the first being Shelby Jump, a white farmer who shot his brother Peter in 1829. Aloysius Sheppard  – known as “Wish” – was a 19-year-old African American boy from Federalsburg when he was charged with raping a fourteen-year-old Caucasian girl named Mildred Clark. He was convicted sentenced to death by hanging, and was hanged on grounds behind the jail that bordered the Choptank River.

The Famous Handprint on the Jail Cell Wall

After Wish was hanged, a handprint appeared on the wall next to the steel door on the outside of Wish’s cell. Some said that Wish gripped the doorway when he resisted being taken to the gallows. This is unlikely because he displayed no other agitated behavior prior to being hanged, and there were many eyewitnesses who said as much. The Newspapers reported that hundreds were gathered to watch the execution.

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

Caroline County Sheriff, James Temple tried to play down the spectacle by obstructing the public view of the execution by having wooden fencing put up around the jail-side of the gallows. But people eager to still watch, positioned themselves on balconies or got in boats and watched the execution from the Choptank River.  One Baltimore photographer came down to shoot pictures of the execution.  He shot one of Wish just before he was taken out to the gallows. (It’s the one shown above). He also took two others – one of Wish and his executioners on the gallows with the rope around Wish’s neck, and the other of the same executioners – still on the gallows – looking down at Wish’s dangling body.  These two pictures appeared juxtaposed on a commemorative postcard with a heading, “The Hanging of Wish Sheppard”

Yes, people.  These were dark days.

Eyewitnesses quoted in Voices of the Land: a Caroline County Memoir state that Sheriff Temple couldn’t bring himself to put his hand on the lever that dropped the floor of the gallows sending Wish to his death. Typically there were four officials on the gallows. Three would place their hand on the lever and the Sheriff would be the fourth hand. They’d all release the lever together so that no one person had to claim responsibility for ending the life of the executed person. The responsibility was shared.  But the Sheriff lost his nerve. An eyewitness said he didn’t appear willing to do it. We’ll never know why. But there are some hints.

Wish had been in trouble before.  In 1912, he was in court for stealing five cents, and was found guilty. In 1913, he was caught stealing a bike and $15 and he went to jail for 18 months. It was just shortly after returning home from that stay that he was arrested again. When the investigation for the rape of Mildred Clark began, the Sheriff went to Wish Sheppard’s home and told his mother that he (the Sheriff) wanted to ask Wish some questions.  When the mother saw her son, she told Wish that the Sheriff wanted to talk to him, and Wish sought the Sherif out to see what he wanted. That was the last time Mrs. Sheppard saw her boy alive. They say Wish confessed to the rape … but later recanted. Most everyone who saw Wish said he was calm and shy and evidently accepting of his terrible fate, including a few children who saw him through the jailhouse window observing the gallows being erected. The kids even talked to him and one of them recounted the conversation when he was a much older man. Allee Allaband, who was born in Tuckahoe Neck told the story.

I talked to Wish Sheppard the afternoon before he had his last supper…Wish had to know what they were constructing because of the people going up and down the hill, but he didn’t seem impressed. Think he had reconciled himself to the fact he was going to be hanged.

The Denton journal reported on August 28, 1915 that on the night before his death, Wish was attended by two black preachers, Rev. J. H. Fitchett and Rev. F. T. Johnson, and four black women. Holding religious services in his cell, they sang and prayed for Wish. The chorus was heard as it floated across the Shoptalk river as far as a mile away.

When Mrs. Sheppard was told about the charges, she said that people must have misunderstood.  Wish was friends with Mildred.  They spent time together. After his death, Mrs. Sheppard was assisted by county officials with claiming Wish’s body in secret so that she wouldn’t be assaulted or the grave desecrated.  He was placed in an unmarked grave  – and the location has long been forgotten.

 Wish is remembered every day at the jail

The original door of the jail cell where the handprint was
The original door of the jail cell where the handprint was

The handprint that he left on the jail cell wall never faded.  Sheriff Temple tried to paint over it. The handprint bled through the paint. The next sheriff – Sheriff William Andrews – also tried to paint over it, and even added plaster. But the handprint eventually bled through again. Sheriff Louis Andrews succeeded his father, William as Sherrif and he placed concrete over the print, but it still bled through. The door adjacent to the wall never worked properly according to Sheriff Louis Andrews. It wouldn’t lock or stay locked. They finally stopped housing prisoners in there. In the

The door adjacent to the wall never worked properly according to Sheriff Louis Andrews. It wouldn’t stay locked. They finally stopped housing prisoners in there. In the 1980s, the jail was expanded and renovated. The door and wall with the handprint were not removed – they were simply “walled over” with a new wall. Today, that wall is in the commercial kitchen. When they were remodleing the kitchen a few years back, they tore down that wall and everyone was surprised to see a wall behind a wall the a door in the middle of it. It was the same entrance to  Wish’s old cell and the wall with the handprint. Unfortunately, the handprint was on the other side of the wall and the door couldn’t be opened. But everyone stood in silence when it was revealed. They all knew what that door was.

And they even took pictures (and shared them with me) … remembering Wish and that awful time so long ago.


According to Sheriff Andrews, the inmates at the Denton jail were tormented by Wish. They’d see him in the hallways; they’d hear him climbing the stairs; they were attacked in their cells and showed scratches and gash marks. A couple of them said Wish grabbed their watches and took them, and the watches showed up broken outside the jail. The sheriff reported that the inmates were often terrified and would call out to him in the night. And he’d come with his lantern – and later a flashlight and point out that there was nothing present. Nothing to be afraid of.

The Sheriff even recounted the story about a famous female inmate named Annie Thomas who was charged with murder. She was on the second level of the jail and chastised the Sheriff one morning for trying to scare her in the middle of the night. She asked him, “Why’d you try to scare me last night, dragging those chains up and down those metal steps?”

Years later in the late 1990s the jail underwent another expansion and the 911 center was added to the building. Dispatchers told about hearing file cabinet doors slam in locked rooms after dark when all the employees had gone for the day. They’d also hear strange noises, doors swinging – sometimes slamming.  But everyone agrees that all the haunted activity happens at night – usually between 2 and 3 a.m.  It seems that after those renovations to the jail building  in the 1990s, Wish turned his focus to haunting  staff, rather than  inmates.


A jail is a unique environment when assesing possible paranormal activity because you KNOW that no one is there. The facility is secured and your job is to monitor the empty spaces.  So if some unauthorized “something” appears to be in those controlled empty spaces it is a REALLY BIG DEAL. One can’t easily explain it away as being a passing stranger or someone showing up whom you didn’t expect.

I interviewed staff members ranging from the warden, to correctional offices, admin staff and building engineers. Most had  30 years in tenure, and they all had stories about Wish Sheppard. Lots of stories focused the Control Room, which is a large windowed area in the center of the jail with expansive views of the hallways and wings, and camera monitors that show the live activity all around the jail. The control room is a secure area occupied by one or more corrections officers.  But all the stories happen in the early morning hours when the inmates are locked in their cells and staff is at a bare minimum – and sitting in the control room unless there’s a reason to leave.

Footsteps on the control room stairway

To access the control room, one must walk up a set of steel spiral stairs which are located a few feet behind the officers sitting at the panels and monitors. Several corrections officers have heard footsteps come up those stairs and turned to find no one there. Imagine what that sounds like – steps coming up a steel spiral staircase just a few feet away.  But no one is there.

Black spot that charges the camera

One instance was particularly disturbing to the guards in the Control Room. A guard on the lower level looked at one of the monitors and saw a black spot in the corner of the room that was on camera. He called up to the guard on the control room mezzanine and said, “Do you see this?”  The officer on the mezzanine said he did see it and switched to a larger view on a big 30” monitor to get a better look.  The black spot started to get bigger.  It moved toward the camera until it finally blocked the camera and the monitor went completely black.  They immediately investigated and found nothing amiss.  No one present. No more images on the camera. The camera was working fine.

Apparitions, Shadows and the Elevator

The guards report seeing shadows walking the halls, loud unexplained noises, doors violently rattling and occasionally a touch that will make the hair on the back of their necks prickle and stand up.  One guard said that once saw a man in black with what looked like a top hat walking along the one of the halls outside the control room.  The elevator also operates by itself (which shouldn’t happen).  When all of the inmates are in their cells for the evening, they’ll hear the elevator start to move, hear the door open — and actually watch the door open on the security monitor, and they’ll see that there is no one there.  No one gets off. No one is on the elevator.

As an observer who got to hear the stories first hand, and was able to walk those halls and sense the energy of that place – including the control room I can attest to feeling the strangest energy I’ve ever felt … but then, I’ve never been in a jail before. It’s a strong energy. A thick presence – neither good nor bad. And yes, one easily gets the that feeling of being watched…but not by the guards and not by the inmates.

Elevator door where shadow of Wish Sheppard was seen on camera
Elevator door where shadow of a spirit believed to be Wish Sheppard was seen on camera.  Photo courtesy of Ron Orendorf.

The Kitchen and the Covered Door to Wish’s Cell

I asked to be shown where the door with Wish Sheppard’s handprint was. They took me to the kitchen and showed the wall that now covered the door and the handprint.  There was a big commercial steamer against the wall.  They warden remarked.  You know, ever since they put the steamer in front of that door it’s never worked right. [laughs] And it’s a brand new steamer.”  It worked fine until we moved it there.” Evidently the commercial steamer developed problems with the circuit board once it was moved in front of Wish’s jail cell door.

Phantom Rings the Bell from the Prison Yard

Miss Faye who has worked at the jail for 34 years said, “I was in a staff meeting in the control room. All the staff was in there and all the inmates were locked in cells. It was after 10pm. The bell rang from the prison yard.  This is how someone signals that they want to enter the jail. But no one could have been in the yard at that hour. The inmates were locked down and the staff was in the control room.” She said she ignored the bell figuring it must be a malfunction.  But rang again. So an officer went out to check the door to the yard – and the yard, but no one was there. 

Cold spots and Rushes of Cold Air

Lt. Brown the Operations Commander who has worked at the jail for for 26 years said that he was alone in the area known as “Booking” when he felt a cold rush of air from behind him. There were no open doors or windows. He spoke to Wish Sheppard – affectionally known by the staff as “Shep.”  He said, “Shep, leave me alone. I haven’t done anything to you.”  The warden reminds the staff to not be afraid. She says, “Don’t worry about the dead. It’s the living the that will hurt you” 

Others have felt that cold rush of air on the back steps of the building going from the second floor to the first.  Staff says you can feel it and expect to feel it whether it’s in the middle of summer or dead of winter, that cold air comes at you at you’re coming up the stairs. It’s a piercing cold.


The Denton Jail Attic
The Denton Jail Attic – Photo courtesy of Library of Congress public domain images

If you’re disappointed that you can’t go inside the jail to feel Wish’s presence, don’t worry. Three of the jail staff said that when they sit on the green benches outside the old entrance, and sometimes Wish will talk to them. There are half columns against the brick wall of the jail and they’ve heard a loud knock coming from those columns. Sometimes they knock back and are answered with more knocks. This is in an unoccupied area of the jail.  Also, Wish sometimes messes with the lights in the attic. 

The attic is purely storage and the Ron Orendorf, who oversees building maintenance stated that no one would ever have a need to go up in the attic at night and the light bulb by the outside center window has been burned out for years. But some people report seeing a light on in the attic in the hours after dark .. and sometimes there appears to be a shadowy figure moving around. The staff has offers no explanation or worries.  It’s just one more thing in a vast collection of unexplained events that occur at the old Denton jail.

Front of the Jail with green benches where Wish "knocks"
Front of the Jail with green benches where Wish “knocks”


I asked the staff when they were all together, “If you had to say “Shep is this kind of guy or that kind of guy, how would you describe him? Is he angry, mischevevious – is he trying to scare you to death? ”  Most of them were silent on the matter. But finally Lt. Brown spoke up. “Shep, is just there.  He isn’t angry or up to something. He just lets us know that he’s there.”

The Warden says she’s never had a personal experience, but there were so many interruptions and disturbances when they were trying to get the kitchen done that she did speak to him and say, “Shep will you PLEASE stop messing with us so we can get this kitchen done!” After that, she says, everything fell into place. She even reached out again and asked for his help when the  septic system kept acting up.  Though her plea was said in jest, she did ask Shep to help fix the unexplained problems with the septic system malfunctioning.  She said that after her plea, the problems seemed to resolve themselves. 

Jeff Porter, who has been working for the jail on and off for 30 years said it best, “Shep was treated badly all his life. He’s just stuck here, reminding us to be nice to one another… not letting us forget the past injustices.”


Sources – Interviews with Warden Ruth Colbourne and her staff; Interview with the late Sheriff Louis Andrew;  Interview with former Warden Charles Andrew; Denton Journal, August 28,1915, Voices from the Land by Mary Anne Fleetwood.

Denton Attic photo courtesy of the Library of Congress, Prints & Photographs Division, HABS MD,6-DENT,2A–19

Photo of Elevator Door inside the jail – Courtesy of Ron Orendorf.  

 Photo of jail door courtesy of Ruth Warden Colbourne