The Cayman Islands, 1939.

Imagine walking down a dirt road late at night.

Maybe you’ve been caught at a family member’s house too late, or work ran overtime. It’s a pitch-black night, a moonless evening.

After all, there’s only one power plant on the island, and it only services a small section of George Town from sunset until 10pm.

As you trudge through the dense bush (it hasn’t been cleared to make way for modern hotels or condos yet), what do you hear?

Are there suspicious noises that turn your head?

Was it just the wind?

Did you see that spectral figure dressed all in white, or was it only the underside of a silver thatch palm?

Caymanians of old tell many stories like this, of times when the veil between our world and the spirit world was thinner. Of quiet, moonlit nights when the spirits of their ancestors would contact them.

As Halloween approaches, we gathered some of these spine-tingling stories. So, if you’re faint of heart, read on with caution!

The accounts below are taken from two sources:

1. Duppies Is, Robert “Bob” Fuller’s 1967 collection of duppy stories told to him by members of the North Side community.
2. The Cayman Islands National Archives’ Memory Bank collection, a library of transcribed interviews with elderly Caymanians undertaken from the 1980s through the early 2000s.

All information is courtesy of the Cayman Islands National Archives’ collections.

Portents of Death

Many sources reported experiencing premonitions of deaths in their family or community, known locally as ‘tokens’.

As Fuller, says: “A number of old timers could foretell deaths from the fact that they often saw and recognized wraiths.” Wraiths are spirits of recognisable persons often seen soon before, at the exact time of, or after their deaths. 

Thomas Watler of Red Bay, who was 58 at the time of his 1991 interview, spoke of his father’s premonitions:

“…so many people believe in extra sensitive perception [extra sensory perception]…[It] was more or less like that, because he would always have a dream about the graveyard, and…someone in the family would die…Back in ’46…there was no telephones or anything, and the only communication was telegrams and things like that. Well, he got up one morning and told my mother, he said, ‘Somebody in the family is dead; I dreamed about the cemetery’, and about an hour later, we had a telegram, his father had died.”

Ira Thompson, a well-known taxi-driver whose collections of artefacts are the foundation of today’s National Museum permanent collection, had this to say:

“I was reaching for the knob of the front door when I chanced to look through the screen window to my left and there looking in was the head of a boy so contorted that I couldn’t possibly have recognized him. I have never seen such agony in all my life. The face only remained for a second or two before it vanished…Later I heard that a young friend of mine had been electrocuted while working on a light pole.”

In 1919, Fred Mac, a respected builder on the island, was away working in the sea trades. He describes lying awake one night in his cabin and looking up to see a woman hanging by her neck in the doorway of his cubbyhole. Using a different passageway, he moved his mattress to the deck, but as he looked up again, the woman was hanging from the beam above him. Spooked, he told the captain that a tragedy must be happening back home. The captain was amused and thought nothing of it. A storm in the area meant it took 16 days to sail home, and when they finally returned, they found an island still in shock. On the very night that Fred had seen the apparition, Vaney Bush had hung herself.

Leila Yates, a well-known nurse who delivered nearly 1,000 babies, was 87 at the time of her interview. She recounted her supernatural experience, which she had never spoken of before.

She was called one night around 11pm to see a child who had suddenly taken ill. While they were waiting for the doctor to arrive, she went to the outhouse (there was no plumbing at the time). While walking back, she heard a noise in the bushes that sounded like cattle or a horse trampling the brambles. She asked the person she was with what it was, but they said there were no cattle on the property. She inspected closer and saw the sister of the child, who had died two and a half years before, standing still in the bushes, dressed in a long white gown. Leila ran ahead but didn’t tell anyone what she’d seen. When she returned to the house to continue waiting for the doctor, the ailing child’s aunt told Leila that the child was dead. It had only been about 10 minutes since she’d seen the apparition.

The May Cow

Most Caymanians know the legend of the May Cow. Originating in Cayman Brac, the duppy is similar to Jamaica’s Rolling Calf. Usually described as a beast dragging chains with fiery red eyes, the May Cow was thought to be the spirit of a person who was excessively cruel in their life.

Physical descriptions of the beast vary. While some say it took the form of a bull, others describe it as more humanoid. Ernest Panton says it was a large, “black as tar” creature that was covered in hair (with some smooth bald patches) and red stripes. Eleanor Grant Bodden’s uncle described the May Cow as having “white spots and black dots and yet he was white all over and he was shaggy, yet he was smooth as a [carboy].”

It is said that the beast’s primary haunt was the Bluff, Cayman Brac’s 140-foot limestone cliff. The men who would go up to the crag looking for mangoes would sometimes encounter the May Cow tearing through the foliage. They’d be forced to climb trees and pelt him with green mangoes until he disappeared.

Headless Apparitions

Several people reported sightings of headless duppies, some human, and some animal.

One interviewee remembered seeing a man and horse appear in front of him; when asked how he knew they were duppies, he replied that neither had heads.

Bob Fuller recounts:

“At the time that the Galleon Beach Hotel was being constructed they rented a house for their English workmen which later they found to be haunted. One of the men was shaving one evening when he noticed something in his mirror indicating that a short man was in back of him. Moving to one side he beheld the reflection of a person without a head. Thinking that someone was trying to scare him he quickly turned around. There was no one there, not even the headless duppy.”

Bill Ration (McCoy), an undertaker for over 40 years at the time that Fuller interviewed him, recalled:

“…a man and a woman were found deep in the bush at North Side. They had been dead for several days when I got there. They were in bad shape. He wasn’t so bad but she was practically gone from her breast up. I worked several days trying to get them out of the bush through a narrow path, putting them in caskets and taking them to East End where they were buried…When I was coming back from East End tired and late that same man was in the road. He yelled, “Stop”. I didn’t and he disappeared. When he did a headless woman jumped out of the bush at the horse and shook her fist at me. He was the same man I had just buried. Of course, I couldn’t be sure about her.”

In another story, a man was driving in Frank Sound after having dropped his ailing aunt to the hospital in George Town. His car suddenly slowed down and wouldn’t accelerate. When he looked next to him, a headless duppy was sitting in the passenger’s seat. It sat there for about two miles while the driver, who was terrified, desperately tried to speed up. Then finally, the car jolted forward and when he looked over again, the ghost was gone.

There are many similar stories of hitchhiker duppies in the Frank Sound area. Sometimes they jumped into moving cars, other times they hopped onto the back of someone’s horse or bicycle. “Practically everyone who used to cross from Frank Sound to North Side in those days had it happen to them if they drove at night.”

These are only a few of the spooky encounters Caymanians of old have reported. There are also stories of being ‘carried away’ by spirits deep into the bush where no one can find you, being punched or choked by malicious spirits, and encountering faster-than-human duppies.

If this has left you a little scared to traverse the dark Cayman roads at night, here are a few tips the elders recommend:

— Never walk alone at night with rum or hard-cake (cassava or corn cake). Duppies love these and will follow you. If you must carry them, be sure to pour out a few drops of your rum to appease the spirits.

—Bring corn with you when walking at night. If you sense a duppy following you, drop grains of corn every few minutes to distract them.

—Many duppies don’t like being asked who they are and will disappear if you ask them for their name.

—If you sense or see a duppy, turn your shirt inside out so it can’t follow you home.

So, walk the roads with caution and be sure to check your passenger’s seat twice tonight.

Happy Halloween!