Haunted History in the Heart of Kissimmee
They still talk about the morning of January 19, 1912. The air was crisp, the crowd pressed against the picket fence, and the rope swung gently in the dawn light. When the trap gave way, a man dropped—and legend says the rope never stopped swaying. Today, workers in the old Osceola County Courthouse swear that same man still paces the third-floor hallway, waiting for a retrial that never came.
Built in 1890, this red-brick Romanesque courthouse wasn’t just the center of civic life—it was the pulse of a frontier community determined to prove its permanence. For $35,000, Osceola County bought itself both progress and ghosts.
The Building That Refused to Retire
By day, it delivered justice; by night, it hosted dances under the same ceiling beams that echoed the judge’s gavel. Electricity flickered on here in 1901, and by 1905 the sheriff proudly held the county’s only telephone. One ring meant moonshiners. Two rings meant a hanging. Death and progress shared a party line.
Those hangings—nine of them, between 1908 and 1912—drew crowds that treated the courthouse lawn like a grim theatre. The gallows stood near a live oak whose bark still bears faint scars. When the final execution shattered every first-floor window, the county planted jasmine vines to “sweeten the air.” They withered, but the stories didn’t.
The Clerk Who Never Clocked Out
John L. Overstreet arrived in 1905 and never really left. For nearly half a century he kept the county’s records in impeccable order, and when he died—while pruning that same oak—locals joked that he simply transferred departments.
Guards on overnight shifts still hear the rhythmic click-clack of a typewriter from his old office at 3 a.m. Contractors have seen cabinet doors fly open in unison. Security cameras have caught a mist settling neatly into the courtroom’s front row—Overstreet’s preferred seat. The docket, it seems, still has his name on it.
Across the Street at Grissom Park
Children play there by day, but after dark the swings creak in perfect rhythm and the laughter turns wrong somehow—too distant, too echoing. Some say it’s the restless spirits of jail trusties buried nearby, still keeping their final watch. Others claim they hear a gavel striking three times from nowhere at all. Locals call it “night court.”
Echo’s Corner 🕯️
“In Kissimmee, justice was swift, but the ghosts were patient. The gallows were dismantled, the dances ended, and still the courthouse breathes between verdicts. Maybe some stories don’t want to be closed—they just want to be heard.”
If You Go
📍 Location: 3 Courthouse Square, Kissimmee, Florida
🕰️ Hours: The building still operates for limited judicial functions; exterior accessible year-round.
🎟️ Tours: Check local ghost walks for seasonal nighttime events.
💡 Traveler Tip: Visit at twilight to see the courthouse lights flicker on—just as the lanterns of Overstreet’s era once did.
Why It Matters
Haunted or not, the Old Osceola Courthouse is a cornerstone of Florida’s frontier history—a reminder that progress often leaves shadows. Every verdict, every dance, every echoing footstep adds another layer to a story still unfolding under the courthouse clock.
So if you find yourself in downtown Kissimmee, stop for a moment. Listen. You might just hear the clerk’s invisible gavel calling court back into session. After all… the docket never sleeps.
Read Next
- Bellamy Bridge Historic Site – Marianna, FL
- May-Stringer House – Brooksville, FL
- Spring Hill Cemetery – Brooksville, FL
Join Ki and Dusty as they uncover the strange, sacred, and sometimes spooky across the South—one backroad at a time.
If you see this after your page is loaded completely, leafletJS files are missing.