Spooky Spots: Ghost Stories and Haunted Sites in Historic Sarasota

Attention ghost hunters: 'tis the season when spooky things are afoot in this sunny, seaside circus town.

Some people say that Halloween is the time of year when the 'veil' between the worlds of the living and the dead is at its thinnest: when the nights get longer, chilly breezes stir the leaves, and ghosts make appearances amongst the living. One may be left wondering: was it really the breeze that rustled those leaves, or was that fleeting chill that passed through the air something... ghostly?

In honor of the Halloween season, we've collected stories about some of Sarasota's most famous ghosts and their favorite historical haunts. Read on … if you dare.

Historic Spanish Point

With an archaeological record that spans at least 5,000 years, Historic Spanish Point could very well be the most thoroughly haunted slice of Sarasota County. The historical site in Osprey is purportedly inhabited not only by the spirits of Florida's earliest native people, but of the area's 19th century settlers and 20th century local icon, Bertha Palmer.

Long before Spanish explorers arrived in the 1500s, the Gulf Coast region was home to some of Florida's earliest inhabitants. The Historic Spanish Point site houses two Native American shell middens and one burial mound—recognized as one of the largest Native American mortuary sites in the southeastern United States. These archaeological sites date back 1,000-3,000 years, and have been reported by amateur ghost hunters to have elevated spiritual activity—most likely from the area's very first residents!

Historic Spanish Point is home to a second burial place, the pioneer cemetery established following the arrival of the Webb family and other settlers—the Guptils, Blackburns, and Roberts—in the 1860s. Visitors to Spanish Point report catching glimpses of these settlers' spirits roaming the grounds among the live oak and gumbo limbo trees. Near the cemetery is Mary's Chapel, named in honor of Mary Sherrill, a 20 year-old guest who arrived at the Webb Resort in 1892 in hopes the Florida climate would ease her tuberculosis. Mary passed away shortly after her arrival, but it is said that to this day, some say that the faint chime of church bells may be heard ringing in her chapel at night.

Chicago socialite, businesswoman and agriculturalist, Bertha Palmer, is among the most influential figures in the development of modern Sarasota. Palmer arrived in Florida in 1910 and established her 350-acre winter estate on the former Webb settlement, now known as Historic Spanish Point. To this day, Palmer's ghost is rumored to stroll through her estate gardens from time to time.

Rosemary Cemetery

Prominent members of Sarasota's founding families were laid to rest in the Rosemary Cemetery—one of the spookiest locales in the city. The site is home to approximately 740 total gravesites, with 380 recorded burials dating back to 1887, and a handful of hauntings.

Figures at rest in the Rosemary include many of Sarasota's original Scotch colonists, its first mayor, Col. John Hamilton Gillespie; local developer Owen Burns; and Rev. Lewis Colson, a pioneering surveyor and prominent member of Sarasota's early black community.

In addition to being Sarasota's first mayor and one of its most influential real estate developers, J.H. Gillespie is recognized for creating the first golf course in Florida—and possibly the United States—in Sarasota. If you are bold enough to roam the Rosemary Cemetery alone, listen closely for the swish of a spectral club as the mayor perfects his swing in the afterlife.

Paranormal experts suggest that some resident spirits are not so lucky to rest in peace like the leisurely, golfing Mayor Gillespie: the cemetery is also home to the restless ghosts of the Green family, who were victims of a grisly family massacre at the hand of their husband and father, Elaf Green, in 1887. Mediums who visit the cemetery report that Mrs. Green and her three children are keen to communicate their unrest from beyond their graves as they roam the Rosemary after dusk.

Theatre District Hauntings

From W.C. Fields to Bette Davis, Cecil B. DeMille, Will Rogers and Elvis Presley—Sarasota was no stranger to the stars from the 1920s through the post-war mid-century, as the downtown theatre district took shape over the decades. Some speculate that Sarasota's deceased celebrity royalty may occasionally return to enjoy a show—like phantoms of the opera paying a visit from beyond the veil.

Downtown Sarasota's historic theatres—the Sarasota Opera House (formerly the Edward Theatre, where a young Elvis performed in 1956), and the Florida Studio Theatre—have their fair share of ghoulish ghostings.

Florida Studio Theatre artistic director, Richard Hopkins, had a series of exorcisms performed on FST's Keating Theatre in the 1980s to dispel disruptive ghosts. The Keating was originally constructed in 1915 as the Sarasota Women's Club, and, Hopkins said, was home to a collection of boisterous spirits who would rap on the walls and shine shafts of light on the stage at random—quite a nuisance for actors practicing their lines!

Employees of the Opera House claim to hear the shuffling footsteps of a more benign spectre, who roams the opera hall at night in search for a theatergoing friend. Some say he also roams the street between the Opera House and the former Golden Apple Theatre—which for 40 years was the nation's longest-running dinner theatre, until it closed in 2013.

Ringling Estate

Business magnate and developer, John Ringling, and his wife, Mable, first came to Sarasota to establish the winter headquarters for the Ringling Barnum & Bailey Circus in the 1920s. The Ringlings also made Sarasota their own winter home, and built their regal Venetian gothic Ca d'Zan mansion to overlook Sarasota Bay in 1925.

Today, the Ca d'Zan is open to patrons of The Ringling—the mansion's neighboring estate art galleries, which house the Ringlings' extensive collection of Baroque and Renaissance paintings—John Ringling's final gift to the state upon his death in 1936. John and Mable made their final resting places at their beloved Sarasota estate, and are buried alongside Mable's rose garden on the Ringling grounds.

Caretakers and visitors to the Ca d'Zan mansion have made numerous reports over the years of encountering John, Mable, and their dog, Tell, in the mansion. Furthermore, mediums report hundreds of ghost encounters in the mansion—no surprise, as Mable and John were avid entertainers and often threw ritzy parties for their friends at the Ca' d'Zan during the Roaring Twenties. Museum docents and guards suggest, too, that the ghost of John visits the art galleries on occasion to admire his beloved collection.

Unfinished Ringling Hotel / Chart House

When John Ringling and then-business partner, developer Owen Burns, began construction on the tragically fated Ringling Ritz-Carlton Hotel on Longboat Key in 1926, they were so confident in the hotel's success that Ringling poured $650,000 of his own money (that's equal to nearly $8.75 million with inflation today) into the project.

Unfortunately for the ambitious developers, their plans for an opulent luxury hotel were built on the edge of the bursting Florida land bubble of the 1920s—just as tourism was receding and the Great Depression loomed. When the bubble burst, so did John Ringling's holdings in real estate, banks and the circus. Construction on the half-finished Ritz-Carlton halted and the building fell into disrepair over three decades before it was demolished. Ringling died bankrupt in 1936, leaving only his art collection behind to the State of Florida.

The overgrown Ringling Ritz-Carlton hotel skeleton first became a haunt for local teens and locals began to call it 'The Ghost Hotel' for its eerie countenance. The site became a scene of tragedy: Sarasota County historian Jeff Lahurd tells the Longboat Key Observer that as many as eight people fell to their death from the hotel before its demolition in 1964. Paranormal experts believe ghosts linger at the site to this day.

Today, the Chart House building and restaurant reside on the real estate formerly inhabited by the shell of The Ghost Hotel. Feel a sudden chill pass through the room during dinner? Don't worry, it's probably just one of the spirits of The Ghost Hotel, who restaurant employees say still wander through the dining room from time to time.

Find Your Favorite Haunts in Sarasota

Do you know any spine-chilling Sarasota ghost stories? Have any supernatural experiences? Share them with us in the comments!