OCALA, FL (352today.com) – With a voice full of history and mystery, Kathleen “Kat” Ramirez led visitors through downtown Ocala on the Historic Ocala Preservation Society’s annual Ghost Tour on Oct. 18 and 25–two nights where local legends and historical fact intertwined.

Ramirez, vice president of HOPS, guided participants through some of Ocala’s most storied and allegedly haunted landmarks.

A woman with red hair, a black hat and a black shirt with white graphics stands in front of a beige house with a Halloween themed wreath hanging on the door and a decorated mailbox hanging on the wall with a horse design on it.
Tour guide Kat Ramirez leads guests through downtown Ocala’s haunted history on the Historic Ocala Preservation Society’s annual Ghost Tour. Courtesy: James Huston

The tour began at the Bryant House, HOPS headquarters and one of Ocala’s oldest preserved homes. Built in 1892 by William Robert Bryant, the Victorian vernacular-style home has deep family ties to Florida’s history. Bryant’s grandson, Cecil Farris Bryant, went on to serve as the state’s 34th governor. The home remains under the care of HOPS, which is currently accepting donations for restoration work on the aging wooden beams.

From here, guests walked through downtown Ocala’s historic neighborhoods, where Ramirez shared eerie stories connected to nearby homes and landmarks. Along the way, participants also admired houses competing in a Halloween decorating contest, blending spooky storytelling with community spirit.

A two-story gray house with a dark rood and white accents is surrounded by trees on a light evening. A woman stands in front of the house with a black shirt and hat.
A dark house with white accents has Halloween decorations including a red light shining on the house, pumpkins, scarecrows and a tall horror figure hanging at the porch.
A gray house with a black roof, white pillars and window accents and brick accents at the bottom of the pillars and house sits two rocking chairs on the porch with trees surrounding it.
A two-story white house with a gray roof and blue accents is covered with a variety of dolls including a Raggedy Anne on the pillars holding up the porch cover and displayed across the yard. Bushes and trees surround the property.

The first tale of the evening occurred at Greenwood Cemetery in Ocala, where guests encountered one of the night’s chilling mysteries–a large headstone featuring a portrait of a woman whose image only appears half-visible when approached under a full moon. “No one’s ever been able to explain why,” Ramirez said.

The tour also passed the Brown House, once owned by a cigar factory owner during a time when Ocala boasted nearly 20 cigar factories. “Cigars built this city before citrus did,” Ramirez said, noting the industry’s decline after the Great Freeze and the shift to citrus–a move that mirrored developments in Ybor City, the historic district to the southwest in Tampa.

The history deepened at Fort King, a site of violent conflict during the Second Seminole War where Osceola led a deadly attack that killed five soldiers. Visitors were told that both the reconstructed fort and its offices are said to be haunted, possibly by the soldiers who never left.

Other stops added layers of intrigue–including La Vittoriana, once a fine-dining restaurant. Legend has it that anyone who tries to move the old painting still hanging inside ends up mysteriously injured.

The Oak Hurst Plantation story drew quiet gasps from the group: After a woman vanished while horseback riding, her grief-stricken husband took his own life. Since then, locals claim a “ghost horse” appears before major tragedies–its last sighting was before the 1883 Brick City Fire on Thanksgiving.

A tall tree has a sign posted on it that reads, "Don't Text And Fly." Behind the tree is a Halloween decoration in the shape of a witch that flew into the tree with a Halloween pumpkin bucket.
A white house with gray accents is surrounded by Halloween decorations including skeleton figures, fake leaves, an orange wreath and other tall horror figures.
A yellow house with red accents on a street is surrounded by trees on a sunny, partly cloudy day.
A group of people stands outside a yellow two-story home with a front porch, listening to the tour guide.

The tour also highlighted the Seven Sisters Inn, widely considered one of Florida’s most haunted places, and The Ritz Inn, now a veterans’ homeless shelter. Once a lively hotspot during the Prohibition Era, a devastating fire there killed multiple guests. “People say you can still hear the screams,” Ramirez said.

HOPS, a nonprofit organization run entirely through volunteers, board members and community donations, continues to preserve Ocala’s past through events like this.

The society’s next event, the Holiday Tour, will be held on Dec. 6. Those interested in joining as volunteers or board members are encouraged to reach out through the Historic Ocala Preservation Society’s website.