October road trip? Creepiest places in Florida guaranteed to haunt your dreams

Sites include several in St. Augustine, along with a few hotels

Full disclosure: Some of the stories below are not for the faint of heart.

Without further ado, here are 20 of the creepiest places you can find in Florida. We’ll start by providing locations, so you can get a rough idea regarding where each spot sits, and then you can read about why each spot is supposedly so haunted or creepy. Be sure to weigh in at the bottom and tell us which site you’d most like to visit.

And before you venture out: Just keep in mind that with COVID-19 still being ever-present in our lives, some of these places might have different hours, rules or circumstances in place -- so it might be worth the effort to do some digging on social media, so you’ll know what to expect.

Be sure to weigh in at the bottom and tell us which site you’d most like to visit.

1. Castillo de San Marcos (St. Augustine)

If we’re talking haunted or creepy destinations in Florida, of course, St. Augustine is going to top most lists.

Let’s talk about Castillo de San Marcos, a former military fortress that’s infamous for some of its battles. Some say the spirits of Spanish soldiers still defend the 17th century fort. Others say a light shines from a fixture in one of the watchtowers that has no electricity running to it. The spooky accounts also include one Spanish soldier in particular who stands at the edge of the fort, looking out to sea just when the sun is about to rise or set. And then there’s the dungeon, where many people have reported the feeling of cold hands touching them. Others say they just felt cold in general while walking through, according to a website called ghostsandgraves.com. Visitors to the fort say they’ve shot videos and photos of glowing orbs, misty shapes and even some shapes resembling bodies. Enthusiasts of the paranormal and supernatural definitely flock to Castillo de San Marcos for a number of reasons -- all of which will make your skin crawl.

2. Flagler College (St. Augustine)

Phew -- there’s a lot going on at Flagler College (if you believe in this sort of thing, of course).

For starters, Ponce de Leon Hall is supposedly home to three spirits: Henry Flagler; Flagler’s second wife, Ida Alicia; and Flagler’s mistress, who is only described as “a woman in black.” And for reference, the original Ponce de Leon Hotel, known now as Ponce de Leon Hall, is the centerpiece of Flagler College. Here’s what hauntedhouses.com says, in a nutshell: Henry Flagler loved his hotel. He died in January 1913 in Palm Beach after falling inside his home. Flagler’s body was laid in state at the hotel’s rotunda. When it came time for him to be carried out, all the doors slammed shut. Although his body was buried at a nearby mausoleum, many believe Flagler’s spirit remained at Ponce de Leon. Another version of this story claims that Flagler was trapped in the rotunda. It’s not uncommon for hotel owners or founders to “stay” or visit their cherished properties, perhaps to keep an eye on things. So maybe it all makes sense. As for Ida Alicia, people say she may have been manic, or that she possibly struggled with bipolar disorder. “(Sometimes), people with (mental health problems) sometimes have a hard time letting go of this earth and passing through the light to the other side,” hauntedhouses.com says.

And finally, according to folklore, Flagler was having an affair with a woman who often stayed at the hotel. She always wore black. When Ida Alicia came to stay at the property, Flagler kept the woman wearing black far away from his wife, and didn’t allow her to leave a certain set of rooms, as the story goes. It’s been said that she went crazy and hung herself. Now, remember: This is just a small snippet of one building at Flagler College. So who knows? The haunted stories can only expand from here.

3. The Florida Theatre (Jacksonville)

The Florida Theatre, built in 1926 and opening its doors in 1927, was constructed on the former site of an old and unorganized police station, which serves as the basis for many of the haunted stories that surround the theater. A manager once said she heard a strange and unexplained humming sound. Other employees have reported spotting weird-looking shadows in the balcony, or odd lights in their photos. Legend has it that a dead motion picture technician from the venue’s early days might still be haunting the place. The theater has hosted at least one paranormal tour, and its creepy factor has been featured on a Jacksonville-area television show, as well.

4. Miami Biltmore Hotel (Coral Gables)

This hotel was absolutely popping during the Prohibition era. Without a doubt, it was the place to be. But then, two major events took place: Thomas “Fatty” Walsh -- of course he’s a gangster, check out that name -- was killed here. And then, in the early 1940s, for World War II, the hotel was temporarily repurposed into a military hospital. That’s when the haunted stories started coming in.

Among those supposedly haunting the joint are: veterans who died in the building during its hospital years, a mother who fell to her death as she tried to save her 3-year-old son who had climbed up on a balcony of the high-rise tower suite, a married woman caught in bed with a lover, and gangsters from the 1920s and ’30s. Still, the luxury hotel is in business even today. It’s a luxury, five-star resort located just outside Miami in Coral Gables. Would you stay there?

5.) Key West Cemetery

This, my friends, is a truly historic cemetery. The website ghostsandgravestones.com says that more than 100,000 people have been buried here -- (!!!) and that many are still lingering between life and death. So take that for what it’s worth. Apparently there are some pretty funny and atypical headstones, for example, one reading: “I told you I was sick.”

“But be aware as you wander amongst the graves,” the website warns. “You may just run into the spirit of the well-known Bahamian woman who sees herself as the guardian of the graveyard. She’ll only approach you if she feels you’re being disrespectful to the gravestones, so make sure if you feel like sitting down, you sit on a bench, not a grave. Visitors have reported this stern ghost approaching them with an angry look upon her face and then disappearing. Other eerie encounters include disembodied voices, shadows and strange orbs of light. Check the photos of your visit, too -- many guests to the Key West Cemetery report various mysterious lights, shadows and figures.”

Well, don’t say we didn’t warn you.

6. Oldest Wooden Schoolhouse (St. Augustine)

“Oldest Wooden Schoolhouse” is right: This is reportedly the oldest schoolhouse in the nation. It’s said to have been built in the early 1700s.

A man named Juan Genoply lived there, and he was passionate about educating children in the area. He and his family stayed upstairs while the school was on the building’s lower level, as the story goes. The family put so much work into the schoolhouse that perhaps they never wanted to leave. Some visitors have said there appears to be a moving light that looks like a candle in a second-story room -- despite the fact that the building is closed at night and no one has lived there in years. Local police have even been called (well, reportedly), but they can’t explain the odd occurrences, either. Others say they can hear the faint giggles of children at the schoolhouse; especially near the area where kids used to play. The good news is, all the spirits seem to be friendly, according to published reports.

7. I-4 Dead Zone

This story is a bit tricky to explain. Roadtrippers.com does a pretty good job, but basically, there has been some “weirdness,” if you will, reported along a stretch of Interstate 4: Think rumors and legends involving pioneer ghosts; ghostly voices, and allegedly, cellphones and radio stations going dead. This could even be one of the most haunted highways in America. A lot of the activity seems to be centered between Orlando and Daytona. Read more.

8. Ashley’s Restaurant (Rockledge)

Here’s the story on Ashley’s Restaurant: Ethel Allen was 19 when she was killed, back in 1934. A local to the area, Allen was found on the shores of the nearby Indian River, according to the restaurant website. She was a regular at Jack’s Tavern -- and this was also the last place she was spotted alive. (Ashley’s Restaurant was originally named Jack’s Tavern). A psychic who has investigated paranormal activity at the eatery claims to have had a vision of Allen’s murder taking place inside Jack’s Tavern. Many people claim Allen is still haunting the business to this day. A manager at Ashley’s says she once saw the feet of a woman dressed in 1930s footwear in the stall next to her -- only to learn the stall was empty. Visitors to the restaurant also have reported seeing ghosts resembling a young woman in the women’s room mirror. Additionally, lights have been seen going on and off, some people say they felt like they were pushed while going up or down the stairs, and burglar alarms have even gone off inexplicably. The legends vary, but the restaurant remains open … so, you could also just come check it out for yourself.

9. The Don CeSar (St. Pete Beach)

In the lobby at the Don CeSar, you’ll want to keep an eye out for the ghost who looks like a smiling man. (So that’s not creepy or anything. Nope, not at all). Anyway, that’s supposedly the hotel’s former owner, Thomas Rowe, who died in 1940. Much like Henry Flagler -- see No. 2 on this list -- Rowe supposedly wanted to hang out and keep an eye on the place. He now walks the grounds with his secret lover, a woman named Lucinda. But they disappear when spotted. The beachfront and the hotel entrance are the two most active paranormal hotspots.

10. Cassadaga (Volusia County)

Cassadaga, a hotel and sanctuary constructed in 1927, is now more of a spiritualist community, according to the site hauntedtravelsusa.com. But it’s largely considered one of the more haunted places in Florida, due to “visitors” such as Arthur.

Arthur resided in in room 22 of the hotel in the 1930s. He would often put a chair at the end of one particular hallway and look out the window, while enjoying a cigar and a glass of gin. He kept this up until his death, but many people say Arthur’s spirit remains. Some even still claim to smell gin and cigars, or feel some sort of presence. Flickering lights, tapping sensations and other paranormal bits of activity have also been reported at the Cassadaga Hotel.

The ghosts seem to be playful and welcoming, reports say.

11. May-Stringer House (Brooksville)

Here’s the deal with this house, according to hauntedtravelsusa.com: John L. May bought the property in 1855 and lived there with his wife and the couple’s two daughters. May died of tuberculosis three years later. His wife, Marena, stayed in the home and eventually married a war hero named Frank Saxon. But then she died in childbirth as she was delivering her and Saxon’s daughter, Jessie Mae, who survived. This brings us to 1869. Jessie died at the age of 3, of unknown causes. She and her mother were buried on the home’s grounds, along with John May and an infant son of Saxon and Marena.

Saxon sold the home after Marena’s death, and it eventually became owned by Dr. Sheldon Stringer. He added 10 rooms to the house, which previously had four, and then started sharing the estate with his medical practice. He was known for helping people who had smallpox and yellow fever. Perhaps the home is haunted by Jessie Mae or some of Stringer’s patients. Staffers at the house have reported hearing and feeling some strange stuff, including footsteps, voices, cold spots and eerie shadows. These events persist even today, the aforementioned website said. “Sounds of a wailing child” are most commonly reported.

12. Bellamy Bridge (Marianna)

So there’s the Bellamy Bridge and the Bellamy Bridge Heritage Trail. Both are involved in some legendary ghost stories. (For reference, the trail is a half-mile long and it offers access to the bridge). To jump to the juicy stuff, Elizabeth Jane Bellamy is considered the official Ghost of the Bellamy Bridge, according to the bridge’s website. You can go on a ghost walk to learn more about her story. The walks are guided and offered after dark. You’ll likely hear about an early 19th century moonshiner’s murder and the tale of a wagon led by a headless driver. Learn more.

13. Arcadia Opera House (Arcadia)

The Arcadia Opera House is definitely on ghost hunters' radars: A paranormal team from Bravo TV has even stopped by to investigate, according to published reports. The two-story, 9,000-square-foot building was constructed after a 1905 fire destroyed most of Arcadia’s downtown. Now, the opera house is best known as a museum and antique shop. It’s been used throughout the years for political events, silent movies, graduations, dances and even a USO operation during World War II. So, safe to say: There’s a lot of history there.

Among some of the “haunted” rumors: Ghosts that are responsible for sounds of laughter and children’s footsteps; an incident involving a child who was heard walking into a room and a spirit being felt (but no living child was ever confirmed); the apparition of a young girl crying; a ghost spotted in the hallway of the auditorium, just left of the stage; and a girl seen in the second-floor corner window. A lot of specifics aren’t known, which perhaps make the ghost reports even more eerie. What would make all these souls (allegedly) haunt the opera house?

14. Sunland Mental Hospital (Tallahassee)

Ghost hunters say they’ve seen all sorts of paranormal activity at Sunland, which closed in 1983. The building was quite the eyesore in Tallahassee for years, that is, until it was demolished in 2006, according to published accounts. While it was open, the center lacked adequate funding and it dealt with overcrowding. Conditions, in a word, were bad. So perhaps it’s former patients who are now haunting the location? There’s no sign of Sunland anymore on Phillips Road, where the building used to sit. According to hauntedplaces.org, relics from the old hospital were collected for the Sunland Asylum wing at the Terror of Tallahassee, which is a local haunted attraction.

15. Ybor City (historic neighborhood in Tampa)

The website yborghosttour.com mentions illicit lovers sealed in the basement of the Orpheum Theatre, a scary story involving Jose Luis Avellana Jr., who allegedly haunts the basement at the Don Vincente Inn (along with his disembodied nurse), a long-deceased shopkeeper who still visits his office in King Corona, and an 8-year-old boy who drowned in the Cuban Club pool and never left.

Intrigued yet? Ybor City is a historic neighborhood in Tampa, in case you’re unfamiliar.

16. Sugar Mill Ruins (New Smyrna Beach)

The people of the Seminole tribe still run through the woods here -- often in the early morning hours, hence, the Sugar Mill Ruins' designation as a so-called “creepy” destination in Florida.

As the stories go, “shadow people” also appear near sunset. The ruins were built around 1830, reportedly on the site of a chapel built by Christopher Columbus, according to hauntedplaces.org. The comments section on the Haunted Places site lists a few questionably “haunted” instances.

For example: “I took a picture with my digital camera at these ruins back in 2014, and while l (was) looking at all (our) pictures in August 2015, I noticed two figures in what look like purple robes. They are transparent and it also appears as if one of the figures is holding a baby -- and you can clearly see the baby’s face.”

Eeeek. Would you visit?

17. Lake Okeechobee (Clewiston)

Lake Okeechobee just might be haunted, as urban legend has it. In the early 1900s, between Kreamer and Observation islands on the southern-most part of the lake, some fishermen came across a whole bunch of skeletons, just lying in the water, according to the website exemplore.com. The skeletal remains obviously are not still out there today, but the stories have spread about the fishermen “catching skulls” out on the mysterious lake.

Some paranormal stories surround the lake towns that border Okeechobee, as well. Also, a massive and deadly hurricane that hit in 1928 impacted at least one large area near the lake. So perhaps these tales should come as no surprise, seeing as where there has been a lot of death and destruction, the haunted stories usually follow.

18. Vinoy Renaissance Resort (St. Petersburg)

Apparently, MLB players are frequent guests here, based on the hotel’s proximity to Tampa Bay, from when teams are in town to play the Rays. A Florida Marlins relief pitcher reportedly had an encounter with some paranormal activity, as did a strength and pitching coordinator for the Pittsburgh Pirates, according to the site haunted-places-to-go.com. And although an athlete with the Toronto Blue Jays didn’t see it himself, his wife and children reportedly witnessed the water in their room turning on and off and the toilet flushing continuously. (That’s probably enough to make you check out).

The popular show “Ghost Hunters” visited the property and noted several unexplained events, as well: For example, a closet door was opened by a falling ironing board -- and Jason Hawes heard two voices while resting in his room. The voices weren’t threatening, but these were enough to give the team some serious pause.

What do you think?

19. Brewster, Florida

The city of Brewster doesn’t so much seem to be haunted -- it’s just, well, a little creepy. And that’s not an insult. Most abandoned cities are kind of eerie, aren’t they? Brewster was founded in 1910 to accommodate workers at a nearby phosphate mine, according to AbandonedFL.com. The city had everything a family might need: schools, a movie theater, a post office and some type of medical facility. But in the 1960s, the company planned to close the town. It was shut down by 1962, and the shops and many buildings were demolished. A chemical plant reportedly remained. And now the area sits nearly empty. Is it a real ghost town? You tell us.

20. Orange County Regional History Center (Orlando)

This site was once the Orange County Courthouse. It’s infamous for being the place where Ted Bundy was tried for the death of Kimberly Leach in 1980. Bundy’s name is even allegedly carved into a table -- although who knows whether it was Bundy who’s responsible for the carving itself, said hauntedplaces.org.

“Weird things happen in the building,” the site reads. “Objects move and levitate and some blame Bundy’s ghost. Others see ghostly lawyers, waiting for trials that finished decades ago.”


*This story was first published in 2017. It has since been updated.