Jessie Mae Still Cries: The Haunted History of the May-Stringer House

Brooksville, Florida

They say three-year-old Jessie Mae still cries for her mother inside this house—more than 160 years after she died. Visitors swear they hear her at the top of the stairs, a small, aching voice calling “Mama…” into the dark.

It’s a haunting thought, isn’t it? A child’s sorrow suspended in time, echoing through a Queen Anne mansion that refuses to sleep.

The May-Stringer House in Brooksville, Florida at dusk, framed by oak moss.

The Dream That Became a Nightmare

In 1855, John L. May built a four-room farmhouse deep in the pine woods of what would become Brooksville. He dreamed of a quiet life for his wife, Marena, and their daughter, Jessie Mae.

But tuberculosis stole that dream too soon. By 1858, John was gone—just thirty-five years old—leaving Marena widowed, pregnant, and alone.

Through war and heartbreak, she stayed. Union patrols rode past her porch during the Civil War; she later married Confederate veteran Frank Saxon. Yet the air in that house was already thick with loss. Locals will tell you the sorrow never left—it just settled into the walls.


From Farmhouse to Queen Anne Palace

By 1903, cattleman Dr. Sheldon Stringer saw potential in the old home and transformed it into Brooksville’s crown jewel. Gables, wrap-around porches, and a witch’s-hat tower rose where rough timber once stood.

Inside, mourning wreaths braided from human hair, a doctor’s chair with leather restraints, and a child’s glass hearse whispered of the era’s delicate balance between life and death.

Today, those artifacts remain under the careful care of the Hernando Heritage Museum—and some say, so do the people who once used them.


The Spirits Who Signed the Guestbook

Ask the docents and they’ll tell you: at least eleven spirits still roam these halls.

  • Marena, ever graceful, glides down the second-floor hallway.
  • Jessie Mae, barefoot and curious, still peers from the banister.
  • Dr. Stringer, coat sleeves rolled, tends to invisible patients.
  • James, the WWI soldier, limps the grand staircase, medals faintly clinking.
  • And high in the attic waits “Mr. Nasty,” whose temper sends EMF meters screaming into the red.

Over eighty paranormal teams—including TAPS of Ghost Hunters—have investigated the house. Their final note is always the same: “Activity confirmed.”


Night at the Museum

On Friday and Saturday nights, the Hernando Historical Museum Association unlocks the doors for those brave enough to wander after dark.

Flashlights flicker. Jessie Mae’s portrait follows your every move. The doctor’s office hums with a pressure you can’t explain, and sometimes a handprint appears on a spotless mirror, child-sized and fleeting.

Upstairs, doors lock themselves. Downstairs, the air grows cold in July. And if you climb the attic steps, you might just hear that infamous growl that has chased more than one investigator right back down again.


Echo’s Corner: Do You See Her Too?

During my visit, one of my photos caught something curious—a reflection, a shadow, and the unmistakable shape of a little girl in a dress.

I know it’s pareidolia—our minds finding patterns where none exist. But in a place where a child’s cry still drifts down the staircase, it’s hard not to wonder.

Maybe it’s just light.
Maybe it’s Jessie Mae reminding us she’s still here.

Do you see her too? 👁️

Hernando Historical Museum sign outside the May-Stringer House

Why the Stories Stick

So why does the May-Stringer rise to the top of every “Most Haunted in Florida” list?

Because this isn’t folklore—it’s history with proof.
Names in diaries, doctor’s ledgers, and yellowed obituaries line up perfectly with the ghost stories.

Because the architecture itself conspires to keep secrets—narrow staircases, wooden echoes, whispering vents.

And because, somehow, this house has endured everything: war, depression, hurricanes, neglect. Every emotion that ever filled it still hums in the floorboards. Paranormal researchers call it the stone-tape theory—that powerful feelings etch themselves into the walls. Whether you believe or not, the May-Stringer makes you feel something.


Personal Encounter

When my son and I toured the house, we came as skeptics. The crowd was loud; we slipped away to explore in silence. We never saw a thing—unless you count the pain in my back from all those stairs—but we felt the weight of the place.

The PIT crew showed us photos of unexplainables. Some I could reason away. A few lingered in the mind long after the lights went out.

That’s what the May-Stringer does: it haunts you with curiosity.

The sitting room in the May-Stringer House

Conclusion

The May-Stringer House is more than an old mansion. It’s a living storybook stitched together with grief, resilience, and love that refused to die.

Maybe the spirits stay because they have more to say.
Or maybe the living just can’t help but listen.

Either way, if you ever find yourself on Brooksville’s Main Street after sunset and hear a faint child’s sob drifting from the hill…
you’re not alone. Everyone who ever lived here is still checking the guest list.

If the May-Stringer House gives you chills, step deeper into Florida’s ghostly past with our visit to Spring Hill & Lykes-Ayers Cemetery


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You might also like Bellamy Bridge Historic Site—where love, loss, and legend meet along the Chipola River.

Join Ki and Dusty as they uncover the strange, sacred, and sometimes spooky across the South—one backroad at a time.

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