Legends & Lore

Trimble County’s old stone jail
has a storied past

Mystery still shrouds story of first female jailer
who took over for her murdered husband

By Konnie McCollum
Staff Writer

BEDFORD, Ky. (May 2008) – uring the early decades of the 20th century, it would have been somewhat unusual for a woman to hold an elected position. Perhaps even rarer would have been an elected female serving as the jailer. But not only did Trimble County, Ky., have a female jailer at its historic stone jail, her first prisoner was the very man who murdered her husband.

May 2008 Madison & Indiana Editions Cover

The story of Trimble County’s first female jailer, Pearl Mahoney Williams, is just one of the fascinating accounts of woe and misfortune that have been woven into the legend of the old stone jail. But her story is so unusual that today a plaque hangs in the Trimble County Courthouse hallway in Bedford recounting her experience.
The first jail built in the country was erected in November 1837, just months after Trimble County was formed. According to Trimble County Historical Society records pieced together by longtime member and former president Donna Stark, the land for the jail was deeded to the county by resident Alvah Chase for $1.
At that time, there was a pond situated on the land, which was also the site of the first county courthouse. William McClellan was paid $3 to work on the pond. Once it was filled in, a log jail 32x16 feet and 10 feet high was built. There was a brick veneer on the jail.
Trimble County resident and local historian Steve Smith said the county paid Jack Pryor $302 to build the jail. Pryor was Bedford, Ky.’s first mayor.
At some point, prior to the U.S. Civil War, a stone jail was erected in the same location as the log jail. A second stone jail, the one that stands today in Trimble County’s Courthouse Square, was erected in 1868 and a second floor was added in 1899. The current stone jail has much of the same stone as the first stone jail. The jail is on the National Register of Historic Places.
Williams’ story begins in 1927, when her husband, James Rollie Williams, was elected as the Trimble County jailer. One Sunday morning, Williams had arrested a drunk, Chester Martin, and was attempting to put him in the jail. Martin, who had been put in jail numerous times for violence and drinking, swore he wouldn’t go back. A blazing gunfight erupted between Williams and Martin right in the middle of the courtyard. Williams was shot in the forehead and died.
Although she was pregnant with her 10th child at the time, Pearl Williams took over the job of jailer until her husband’s term was completed. Her first prisoner was Martin. Pearl was then elected on her own for two consecutive terms.
In March 1934, she committed suicide.

Pearl Williams

Local lore has it that she “went into the garage and mixed herself up a potion.” A 2001 book entitled “Pearl,” written by her granddaughter, Lauren Rose, states the lady jailer committed suicide because she listened to her own daughter’s rape by her uncle and did nothing to stop it. Apparently, it was Rose’s mother who had been the victim and recounted the incident to her. That account has raised much controversy with townspeople and other family members who dispute it, said Trimble County assistant director Betsy Tweedy.
Rose noted in the book that her grandmother’s large brood of children went to live with various other relatives after her death. The book is available at the Trimble County Public Library.
It is not clear why, in 1837, the newly formed county needed a jail, but Smith suspects it may have been to house slaves who had been caught trying to escape their masters. “I suspect the jail was used more than anything for runaway slaves,” he said. “It would have been a concern at that time.”
Indeed, one of its first inhabitants may have been abolitionist and former slave Henry Bibb. He was born in 1815 to a slave woman named Mildred Jackson, a mother of seven who worked on an Oldham County plantation owned by Willard Gatewood. Bibb’s father was State Sen. James Bibb, although he never met him. As a child, Bibb saw each of his brothers and sisters sold to different slave owners and he, himself, was hired out to various slave holders.
During his teen years, Bibb married another slave woman, Malinda, and they had a daughter named Mary. When he was in his 20s, Bibb was moved to a plantation in Bedford, Ky., to be with Malinda.
Bibb escaped the farm and went north in December 1837. But he returned for his family in June 1839. His first two attempts to free them failed, and after a failed third try in 1839, the family was imprisoned in a workhouse in Louisville.
After two years in the workhouse, Bibb was sent to Louisiana and by 1842 had managed to escape north again. After finding that Malinda had been sold into prostitution, Bibb decided to dedicate his life to helping other slaves. He began lecturing on slavery and became one of the best known African American anti-slavery activists. He eventually remarried Mary Miles of Boston, and they later moved to Canada. Bibb helped establish Canada’s first African American newspaper, “Voice of the Fugitive.” Bibb died in 1854.
Noted Underground Railroad researcher Diane Perrine Coon, who has done extensive work on anti-slavery activity throughout the area, said it was at some point around 1839 that Henry Bibb was actually housed in the Trimble County Jail, which at that time would have been the log jail.

Henry Bibb

“When he was first caught and jailed for escaping, he was chained to a tree at the local blacksmith’s,” said Coon, of Louisville. Later, he was moved to the jail, where he purportedly told two other runaway slaves how to escape to Canada.
“Two slaves, King and Jack, came to the window at the jail to find out how to escape and get to Canada,” said Coon. “Apparently, they made it.”
Bibb was not the only abolitionist housed at the jail. According to Coon, African-American Elijah Anderson, called the “Superintendent of the Underground Railroad” in Madison, Ind., spent time there before being transferred to the Kentucky State Penitentiary in Frankfort, Ky. Anderson, a free black man from Virginia, moved to Madison around 1839. He was credited for bringing close to 1,000 fugitive slaves across the Ohio River to Madison.
With a $1,000-price on his head and targeted by a pro-slavery mob, Anderson moved his operations north to Lawrenceburg, Ind. He would take large groups of runaway slaves up to Cleveland, Ohio. In 1856, while traveling through Boone County, Ky., Anderson was caught by a Pinkerton agent, who brought him to Carrollton, Ky.
He was accused of helping a slave owned by Gen. William Butler escape. He was tried, but there was not enough evidence to convict him. “He was literally standing on the steps of the Carrollton Courthouse, having just been released, when a Trimble County sheriff re-arrested him,” Coon said.
It was during his stay in the Bedford stone jail that he was convicted of helping runway slaves. “It was the testimony of Madison slave catcher Right Ray that convicted him,” said Coon.
He was sentenced to 10 years at the state prison. On the day of his release, Anderson was found dead. Many believe he was the victim of foul play.
Female abolitionist Delia Webster’s history is also tied to the little stone jail in Bedford.
Webster, a teacher from Vermont, moved to Kentucky and in 1844 helped Methodist minister Calvin Fairbank transport the slave Lewis Hayden and his family to Ohio. Hayden went on to become a prominent abolitionist and businessman in Boston.
Webster and Fairbank were arrested and imprisoned in Kentucky. Webster, because she was female, was pardoned and released after serving just a few weeks at the Kentucky State Penitentiary.

Photo by Don Ward Trimble County’s old stone jail sits in the courthouse square in Bedford, Ky., but it is no longer used to house prisoners. Today, it houses only legends of years past.

In 1852, she and several others, including John Preston, purchased a farm along the banks of the Ohio River for $9,000 in Trimble County. It has been reported she secretly continued to assist runaway slaves, although her reputation, livelihood, and property were under constant attack.
The Preston Plantation (as the farm is called) was the plantation from which “Eliza, one of the slaves in Harriet Beecher Stowe’s “Uncle Tom’s Cabin, was supposed to have escaped from after running away from a cruel master.
In March 1854, Webster was imprisoned in the Trimble County Jail. Reports said it was a cold, late spring and there was still snow on the ground that year. One night while she was in the prison, the temperature fell below freezing, and authorities finally consented to light the jail’s stove. Unfortunately for Webster, there was no vent, so the jail was warm but smoke-filled. Authorities at the time later admitted they wanted her to be uncomfortable. She was freed in April of that same year. She moved to Madison and sold the farm.
Today, the little stone jail is not used to house prisoners. Trimble County Judge-Executive Randy Stevens said it was during the early 1980s that the state decided the jail no longer met state standards.
“The last few prisoners in the jail were arrested for public intoxication during the annual Madison Regatta,” he said. “Today, it is used for storage, but people frequently come by asking about it.”
It is not open for public touring.