The phantom prisoner who made this Madison County bridge Iowa’s most haunted

The Madison County Jail Escapee’s Vanishing at Roseman Bridge

In 1892, a prisoner broke out of Madison County Jail and ran for his life. The sheriff sent men to hunt him down, soon tracking him to Roseman Covered Bridge.

With quick thinking, the sheriff split his posse, blocking both ends of the 104-foot wooden bridge. The trap was set.

Yet when gunshots rang out inside, something odd happened. After a blood-chilling scream, the lawmen found no trace of the man.

He had simply vanished. No body turned up in the river below.

The town soon decided that anyone who could pull off such a trick must have been innocent all along.

Today, Roseman Bridge still stands in Iowa, where visitors claim to feel cold spots right where the phantom prisoner disappeared.

A Prisoner Made His Break From Winterset’s Jail

A man broke out of Madison County Jail in Winterset, Iowa in 1892, sending the small town into a panic. He slipped away early in the morning when guards weren’t paying attention.

He ran southwest into the countryside to get far from the jail. Deputies noticed he was gone during morning count and spread the word across the county.

News traveled fast through Winterset, a town of just 3,000 people, moving quickly across dirt roads and farm fields.

The Sheriff Rounded Up Local Men For The Hunt

Madison County’s sheriff quickly gathered men to catch the runaway. He called all his deputies and swore in temporary officers to help search.

Local farmers and townsmen grabbed their rifles and joined, bringing horses to cover more ground. The sheriff split the volunteers into four groups, each searching different areas around Winterset.

Tracking dogs from nearby farms helped by smelling the escapee’s clothes left in his cell.

Footprints Led The Posses Toward Middle River

The runaway left clear tracks heading southwest through muddy spring fields. Trackers in the posse followed broken twigs, crushed grass, and footprints across the countryside.

By mid-afternoon, all clues pointed toward the Middle River area about six miles from town. The new Roseman Covered Bridge was the only crossing for miles in either direction.

The sheriff realized the 104-foot wooden bridge created a natural trap where they might corner their target.

Cornered At The Red Wooden Bridge

Several men spotted the escapee near the covered bridge around sunset. The runaway, tired from running all day, rushed into the wooden structure over Middle River.

The bridge had solid walls and a roof, making it like a tunnel across the water. The sheriff’s men quickly blocked both ends, cutting off all escape routes.

Farmers lined the riverbanks below to catch the prisoner if he tried jumping from the bridge.

A Clever Trap Was Set At Both Entrances

The sheriff came up with a simple but effective plan to catch the cornered man. He split his men evenly between the north and south entrances of the covered bridge.

Armed men took positions at both openings, creating a two-sided trap. The lawmen readied their guns and lit lanterns as daylight faded.

The sheriff told them to move slowly from both ends, leaving the escapee nowhere to hide inside the wooden structure.

Lawmen Closed In From Both Sides

At the sheriff’s signal, posse members entered the bridge from both north and south at the same time. Their boots made hollow sounds on the wooden planks as they moved forward carefully.

The inside grew darker with each step, as the bridge’s walls blocked the evening light. Lanterns cast strange shadows along the wooden walls as both groups moved toward the center.

The fugitive found himself trapped between two lines of armed men in the narrow passage.

Gunshots Echoed Through The Wooden Structure

Without warning, gunfire broke out inside the bridge. The small space made each shot sound much louder.

Several posse members fell wounded in the chaos, though stories differ on who fired first. Thick gunsmoke filled the enclosed space, making it even harder to see in the dim light.

The sound of gunfire carried across the countryside, bringing more curious farmers to watch the commotion.

A Bone-Chilling Scream Froze Everyone In Place

A terrible scream suddenly cut through the gunfire and smoke. People who heard it said it was an inhuman, blood-curdling cry unlike anything they knew.

The horrific sound stopped the posse members in their tracks, halting the advance from both sides. Several men later said the scream seemed to rise upward through the bridge rather than echo across it.

The sound hung in the air before fading away, leaving an unnatural silence.

The Prisoner Vanished Without A Trace

When the smoke cleared and lawmen got their nerve back, they searched every inch of the bridge. They found no body, blood trail, or any sign of the prisoner inside.

Posse members checked the river below and the surrounding banks but found nothing.

The escapee had completely disappeared despite being trapped between two groups of armed men in an enclosed bridge with no exits. The confused sheriff ordered searches all night using lanterns, but the prisoner was gone.

Locals Couldn’t Explain The Impossible Escape

Madison County folks talked about nothing else for weeks after the incident. No one could explain how the prisoner escaped from a completely surrounded bridge.

Some thought there might be secret trapdoors or hidden passages, but careful checks of the bridge showed none. Others believed the man somehow slipped past in the confusion and smoke.

The community slowly decided that anyone who could pull off such an amazing disappearance must have been innocent.

The Bridge Gained Its Ghostly Reputation

Roseman Bridge immediately became known as the “haunted bridge” throughout Madison County. Visitors reported strange phenomena when crossing, especially at dusk.

Many claimed to feel sudden cold spots in the center where the prisoner vanished. Others heard unexplained laughter or footsteps when nobody else was present.

The 1892 incident transformed the ordinary covered bridge into a local legend, with generations of teenagers daring each other to cross it after dark.

The bridge’s supernatural reputation persists today, drawing curious visitors hoping to experience its ghostly history firsthand.

Visiting Roseman Covered Bridge, Iowa

You can visit Roseman Covered Bridge at 2451 Elderberry Avenue in Winterset for free anytime. The bridge is 7.5 miles southwest of town on gravel roads and only allows walkers and bikes, no cars.

There’s a historical marker telling about the 1892 phantom escape when a jail escapee mysteriously vanished during a shootout with sheriff’s posses, creating Iowa’s most famous ghost story.

A nearby gift shop has souvenirs but check their hours first.

This article was created with AI assistance and human editing.

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