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Visit Florida’s Creepiest Haunts This Halloween

by Erin St. Pierre

Within its pine forests and sandy beaches, Florida has a long, well-documented history of the odd and macabre. Check out these five hair-raising haunted hot spots in the Sunshine State this Halloween.

Fort Zachary Taylor – Key West

By Moon lake airs – Own work, CC BY-SA 4.0

At the western edge of Key West, a name that literally translates to “Bone Island,” lies Fort Zachary Taylor. Many men perished during the construction of the fort from 1845 to 1866. This death count increased during the Civil War, Spanish-American War, Cuban Missile Crisis and yellow fever outbreaks.

Visitors and park staff have witnessed these deaths playing out before them—spotting the ethereal remnants of bloated corpses floating toward the beach, soldiers gathering in formation and the sounds of gunfire from long dormant cannons.

May-Stringer House – Brooksville

Source: Wikimedia Commons

This painted-lady Victorian home began as a simple, four-bedroom house built by John L. May, in 1855. Now known as one of the most haunted houses in Florida, the May-Stringer House has witnessed a known 11 deaths since then. The first being that of John L. May, who lost his battle with tuberculosis.

John’s wife, Marena, later remarried and died during childbirth. Her daughter Jessie Mae survived the birth, only to die three years later from undocumented causes. John, Marena and Jessie were all buried on the property.

Ghost hunters have reported seeing a man named Gary who haunts the attic and may have come to the house attached to a donated antique trunk. There’s also a mysterious woman with her hair tied into a bun and Jessie Mae, who gets upset when people move items in her room.

Micanopy Historic Cemetery – Micanopy

Walking through the Micanopy Historic Cemetery transports visitors into a setting usually reserved for Southern Gothic storytelling. Spanish moss dangles listlessly from majestic live oaks over the eternal residents. Many of the epitaphs on gravestones are still legible, like that of the cemetery’s founder Dr. H. Lucius Montgomery Sr. Weather and time have erased the names of others.

Established in 1826, this cemetery holds centuries of stories among its 2,000-plus gravesites. Today, the land is almost full. The town of Micanopy has plans to expand, but there’s a catch—that land was the site of the Battle of Welika Pond during the Second Seminole War in 1836. And because of the number of unmarked graves, the Micanopy Cemetery Association does not want to risk digging into the preexisting spaces.

Between the Seminole War battlefield and the thousands of residents of buried there, the Micanopy Historic Cemetery holds countless opportunities for a paranormal sighting or two.

Castillo de San Marcos – St. Augustine

Buried within the walls of the Castillo de San Marcos lies a tale of love, deceit and death. As the legend goes, in the late 1700s, Spanish Colonel Marti came to the fort with his young wife Dolores. Dolores was enigmatic and loved to wear strong perfumes. She attracted the attention of her husband’s next in command, Captain Abela, who was much closer to her age.

After the colonel smelled his wife’s perfume on the captain, he flew into a jealous rage. He locked them in a secret room in the fort’s dungeon and left them to die. Today, visitors claim to smell Dolores’s sweet perfume near the area.

It’s no surprise that the nation’s oldest masonry fort has seen its share of bloodshed, starting with attacks by the English in 1702 and 1740. During the next centuries, the fort housed Native Americans the U.S. claimed as prisoners of war. This included the Seminole, Apache, Cheyenne, Arapaho, Kiowa, Comanche and Caddo people.

Visitors looking for a chilling ghost sighting might just find it in the form of Spanish soldiers patrolling the fort or a former prisoner jumping to their death.

Dozier Memorial – Marianna

The history of the Dozier School for Boys feels like something out of a fictionalized horror film. Yet, the horrendous stories from this reform school are all too real. The state of Florida opened this institution in the rural panhandle town of Marianna on January 1, 1900, and closed it on June 30, 2011.

In the last few decades, a group of former school residents lobbied to have the school shut down because of the atrocities that took place there. Forensic specialists, archeologists and investigators are still searching for about half of the boys who died at the school, with only around half of the deceased children having a marked burial site.

Though most of the school grounds are off limits to the public, the state of Florida unveiled the Dozier Memorial on site for visitors to pay tribute to the victims of a real-life horror story.

As a regular traveler and resident of Florida for over 30 years, these are just five of Erin St. Pierre’s favorite spooky places, rich in history with memorable stories to tell. For more examples of her work, please check out Micanopy: Visit Old-Florida Like a Local and Ximenez-Fatio House: Where History Comes to Life in St. Augustine. You can also view her website.

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  • Karen McGrail / September 18, 2023

    This article is extremely fascinating. I’ve lived in Florida for 33 years and never knew most of these places existed. I will be adding several of these to my “must see list. ” thank you for sharing these people’s stories.

    • Erin Z. Bass / September 19, 2023

      This is so great to hear, Karen!