Old Princess Anne Jail

A stone-walled jail rebuilt after prisoners burned the original, now a police station where officers and dispatchers report encounters with a frightening female apparition.

The Grey Eagle, as locals call it, stands as Somerset County's only nineteenth-century structure with three-foot-thick Port Deposit granite walls. Built in 1857 after prisoners burned down the original jail and escaped, authorities determined stone walls would prevent another breakout. The imposing building served as the Somerset County Jail for 130 years until 1987, housing some of the Eastern Shore's most dangerous criminals behind its impenetrable walls.

The jail's darkest chapter unfolded on October 18, 1933, when a mob of over 2,000 white residents stormed the building to lynch George Armwood, a 22-year-old Black man with cognitive disabilities. Despite 25 officers throwing tear gas, the mob used fifteen-foot timbers as battering rams to breach the doors. Captain Edward McKim Johnson was knocked unconscious. Deputy Norman Dryden was forced to surrender his keys. They found Armwood hiding under his mattress, placed a noose around his neck, and dragged him down the steel stairway by his feet. Before hanging him, the mob cut off his ears and ripped out his gold teeth. His body was then tied to a truck, dragged through town, hanged from a tree in front of Judge Duer's house, and finally burned at the courthouse corner. Despite 42 witnesses testifying before a grand jury and state police identifying nine leaders by name, no one was ever convicted. Armwood was Maryland's last recorded lynching victim, though his guilt was never proven in any court.

When the decrepit building faced demolition in 1999, the Town of Princess Anne chose restoration instead. The 2003 renovation transformed the Grey Eagle into the Princess Anne Police Department headquarters, but workers encountered something disturbing. Tools flew across rooms on their own. Windows opened and closed without anyone touching them. Phantom footsteps echoed through empty corridors. Disembodied voices filled the air. The activity became so intense that construction crews refused to work alone in the building, and almost no one would stay after dark.

Police officers and dispatchers who now work in the building have their own encounters. Televisions switch on by themselves. Shadows appear on walls with nothing to cast them. Most disturbing are the phantom voices that appear on recordings during investigation interviews—voices that weren't present when the interviews were conducted. One day, a dispatcher working alone brought her children to the station. Her son explored upstairs, then came back down visibly shaken. He told his mother he had encountered "a lady" who appeared to be "sick"—a frightening woman in a part of the building where no one was present. The apparition is believed to be a former inmate who died in custody.

In 2012, a guest on the Princess Anne Ghost Walk photographed the jail with her smartphone and noticed something in the window. When the image was enlarged, a face appeared with stunning clarity—not a blurry orb or streak of light, but distinct features including a hairline, eyebrows, nose, cheeks, and mouth. The phantom face appears to be that of a small boy, visible in the lower center pane of the center window. What makes this even stranger is that no flooring exists behind that window—only a steel staircase below, leaving the second-floor window open to the first floor. No living person could have been standing there.

Paranormal researcher Mindie Burgoyne, author of the Haunted Eastern Shore books, explains that "a lot of jails are haunted, but think of all the negative energy that's inside a jail." The Princess Anne tour is described as her most disturbing walk, with content so harsh that children are not permitted to attend. George Armwood isn't the only spirit at the Grey Eagle, but he is among the most active. The racially-charged violence that occurred here left a particularly nasty kind of energy behind—one that forever changed this building and continues to make its presence known to anyone who dares work within its granite walls after dark.