The Eastern Shore, like most places with a long history, has its share of legends that are scoffed at in the light of day, but aren’t as funny after the sun goes down.

In the old days, Shore folk talked of will-o-the-wisps or jack-o-lanterns. These mysterious marsh lights would appear at night, hover and dance in the near distance, luring the observer towards them. They were said to protect treasure, but to follow one was to court a watery grave. Children and lost travelers were particularly susceptible to their glamour. Science suggests decaying bacteria beneath the marsh’s wet soil release gasses create the heatless blue or white illuminations, which is far less disturbing hypothesis than is the beckoning of evil fairies or the souls of stillborn children that were once believed to be the culprits behind the phenomenon.

empty brown boat on body of water

In 1712, a woman from Talbot County was prosecuted in Maryland’s last witch trial. Charges against spinster Virtue Viol included using sorcery to “waste, consume and pine the body of a certain Elinor Moore…” and to “…lame & render speechless” the same. She did this “most wickedly & diabolically” and “to the great displeasure of Almighty God & against her majesty’s peace…” Despite such fiendish charges, an Annapolis jury, perhaps tiring of the colonies’ witchcraft-fever, acquitted the Eastern Shore woman.

brown house on hill

Ghosts abound.

Haunted houses, and other ghostly landmarks, pock our Shore. Most folks who have been around here a while know about these places and are never surprised when reports of supernatural occurrences circulate.

Many private homes with ghostly reputations were once commercial concerns, such as hotels or funeral parlors, and a lot of old residential properties have been transformed into businesses like restaurants and retail space. Real estate, regardless of its use, sometimes seem not to have shaken off past owners long expired from this mortal coil.

empty house

On Kent Island alone: Generations of staff members from the various restaurants that have operated out of one particular location know about the apparition named Sarah. As the abandoned Love Point Hotel deteriorated, its reputation for being haunted blossomed. On Romancoke Road, near Batts Neck and the Elks Lodge, there have been reported sightings of a well-dressed headless horseman in white shirt and black tie. One old Islander identified the haunt to Trudy Truitt Guthrie as “Mr. Griff Hubbard. I would have known him anywhere.”

Even without his head, apparently.

Shallow of People Inside Room With Fireplace and Armchair Painting

An ex-employee of a popular local bed and breakfast inn tells tales of the early days of the establishment’s opening to the public:

“I have a lot of personal experience with the ghosts (there). The one that gave me crazy goose bumps was one night when (another employee) and I were closing up and we had gone into that tiny ladies room to change out of our lovely uniforms we used to wear and into our party clothes. We were walking back thru the living room through the door that stayed open all the time. It had a lamp stand against it so no one would close it and led into the foyer area with the grand stairs, Well, we went through that door chattering away about all the money we made that night and how quickly we could make it to (the local tavern) No Place. By this time we are in the bar area when T. turns around because she forgot something in the ladies room, and son of a gun, that door to the living room was closed. It only took a few seconds to walk through there and we were only 10 feet from the door and we heard nothing. Actually I think T. even asked me why I shut the door to the living room. I responded that I hadn’t shut it and she started back peddling. As I turned the knob to open the door…it was stuck! Wouldn’t open. T. and I looked at each other like WTF???? Now the hair is standing up on my arms and I reach for the knob a second time and the door flies open. By the way, I think T. was hiding behind me the whole time!  We walked into the room and the lamp stand was in the middle of the floor and when I walked over to put it back where it belonged I felt the breathe on the back of my neck. That did it…We ran like hell. (We) started changing in the Pennyworth room which was the original Library next to bar area after that.

“And of course, I can’t count how many times at end of day when I would walk around and check on all the rooms the pipe tobacco smell that would be so potent you knew someone was standing right there smoking it. It was creepy.”


And aliens?

Soon after the Bay Bridge opened in July of 1952, Unidentified Flying Objects tried to steal its thunder. Over several nights during that sticky hot summer, UFOs were spotted from the Lower Shore to the seats of power in Washington D.C. Though no mention of the events can be found in local newspapers, the Washington Post and Baltimore Sun both featured articles on their front pages. These mysterious events were seen by hundreds, if not thousands of people, including air traffic controllers, commercial airline pilots, and military personnel.


Even gory urban legends make an occasional appearance. For years Queen Anne’s County teenagers heard about a young couple who “ran out of gas” near Piney Creek. The boy went to get gas, but never returned. The girl fell asleep in the car despite an odd scratching on the roof that went on throughout the night. In the morning it was discovered a homicidal psychopath had hung her eviscerated boyfriend over the vehicle and the scratching was his fingernails.


Certainly, the most celebrated phenomenon in the modern era has been the reports of a mysterious 30 to 40 foot long Chesapeake Bay serpent, affectionately named Chessie. Seen at various times and places, the Chessie frenzy was concentrated in the waters surrounding Kent Island during the 1980s. After numerous reports over a couple years, the creature was videotaped early one summer evening in 1982 by a family on Love Point when it broke the surface of the water near a group of swimmers 200 feet offshore. The three minute tape has been scrutinized by various experts with no clear consensus as to what it shows. It was enough to draw national attention, however, and several media organizations, including network newscasters cast the spotlight on a Chessie, who possessed either the bad manners or good sense not to again accommodate the cameras.


By 1985 Chessie was spotted with a companion and entrepreneurs were offering Chessie Cruises. After a while, sightings tapered off, although there are still occasionally new reports. Naysayers speculate witnesses are actually seeing such natural phenomenon as detached oil spill containment equipment or displaced marine animals, and a 1980 photograph was ultimately identified as a stray manatee. Others believe Chessie could be anything from a mutant eel to a surviving prehistoric monster to an escaped giant anaconda.

Whatever Chessie is or was, he or she is a star in the Eastern Shore’s pantheon of legends.


Feature image courtesy Daniel Jensen. Other photos courtesy of Brian Minear, Nathan Wright, Zoltan Tasi, Cluttersnap, and Nicole Harrington via Unsplash.com


Books by Brent Lewis are available on Amazon.com


Remembering Kent Island: Stories from the Chesapeake and A History of the Kent Island Volunteer Fire Department published by Arcadia Publishing & The History Press:




  1. I too have a lot of personal experiences with ghosts, in fact I studied under the top exorcist in Baltimore for six years… but that’s another story. I am continually amazed by your knowledge of our counties early history, especially when considering how misled humanity can become in the “signs of their times”! Kudo Brent, love reading your posts!

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