The approaching Halloween event marks the beginning of the Holiday Season — and I seriously love the holidays! Temperatures begin trending a little cooler and less humid, Tropical Event Season starts ramping down, and costumes and Halloween décor appear in the stores. As someone once sang, “It’s the most wonderful time of the year!”

Now is a good time to look at some of our islands’ spooky ghost stories, and there are a few worth mentioning. And not all of them involve Robert the Doll. So on the eve of All Hallows, let’s look at a few of the Keys’ most spooky stories.

Ernest Hemingway once said that he wanted to live in his Key West home even after he was gone. I guess it isn’t a bit surprising that people have seen Hemingway’s ghost in his study or peering out of a window around midnight. If you had lugged a full-length urinal several blocks on your back from the original Sloppy Joe’s location to your backyard, would you want to ever leave?

Allegedly, Ernie’s isn’t the only ghost at the Hemingway house. His second wife, Pauline, also loved the house, and visitors have reported seeing her inside. So if you visit this historic site, and you hear the sound of a typewriter in the middle of the night, you can rest assured that there may be new Hemingway books to read in the afterlife.

What was the original Sloppy Joe’s location is now famous as Capt. Tony’s Saloon, started by the legendary Captain Tony Tarracino in 1958. Over a century before that, however, the building doubled as an ice house and the Key West Morgue. A tree that has grown through the building was known as “The Hanging Tree,” and supposedly 16 pirates and one woman lost their lives there. During renovations (or perhaps as the result of a hurricane), up to 15 bodies were discovered/uncovered. They were interred there and remain to this day.

The woman who died there is known as the Lady in Blue, and her ghost allegedly haunts this popular haunt. According to legend, she wore a blue dress when she murdered her husband and children, and that was the color her skin turned after she was hanged. Employees and visitors have reported seeing her “hanging around,” and who can blame her? Capt. Tony’s is a fun place!

The Carysfort Reef Lighthouse off Key Largo is the oldest lighthouse in the United States — and is allegedly haunted by one of its former keepers. Captain John Whalton cam down to Carysfort Reef in 1924 to anchor a lightship that would warn mariners of the dangerous reef. Still, 64 ships sank from 1833 to 1841. And in 1834, Whalton and his family were slain by Seminoles. A gentleman named Captain Johnson became the first keeper of the lighthouse after it was completed in 1852, but he died shortly thereafter. 

The keepers that followed him claimed to hear and see some spooky sounds and sights. Imagine yourself alone on a lighthouse in the middle of the night hearing the sounds of moaning and chains rattling. One lighthouse repairman claimed to have seen a human skeleton appear out of nowhere, then disappear into the crystal turquoise waters beneath the lighthouse. Scared keepers kept an open Bible by their bedside to ward off the spirits. 


The Key West Cemetery is popular with visitors who come to pay their respects and get a sense of Keys history. More than 100,000 people are reportedly spending their eternal rest in this tropical graveyard, more than four times the current living population. But you better be careful if you don’t show the proper respect to the departed! In addition to the expected disembodied voices and unexplained shadows, the spirit of a Bahamian woman appears to visitors who disrespect the deceased by walking over their graves or sitting on headstones. If there’s anyplace you don’t want to encounter a belligerent Bahamian ghost, it would have to be a cemetery.

That brings us back around to this Halloween. This is always a special holiday for Middle Keys residents, with some really nice things that happen for our younger people. The neighborhood Behind The Airport (BTA) always goes above and beyond to provide a safe place for trick-or-treaters and young people to dress up and have a scary good time. The event will go on as it does every year on Halloween, and the Sheriff’s Office will provide traffic control and public safety services as they do each year. Also, the Zonta Club will host a safe, socially distant Drive-Up Halloween on October 31 at Marathon Community Park from 5:00 – 7:00 p.m. Little ones will get treats, and everyone stays safe. Finally, it seems there will be a Halloween event at Gulfside Village this year, which typically provides treats to the very young ghouls and goblins.

Whatever you do, make your Halloween safe and fun! And spooky!

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