Delia Ann Webster: The Petticoat Abolitionist of Kentucky

I first learned of Delia Ann Webster from an event my DAR chapter held last Summer. I didn’t think much more about her until this past Fall when I was headed out to Henry County. While planning for that visit, I referred back to my Kentucky county map and realized that Trimble County was just 25 more minutes down the road. It was a county I had not yet visited. I began looking for some historic site that I could visit to make a post. (My goal is to eventually complete at least one historic travels post for each KY county!) I came up empty, so I thought I could at least visit the county courthouse. I began looking into the history of the courthouse, and that’s when I came upon the Old Stone Jail. Bingo! I had a historic site! The site became even more significant when I then read that Delia Ann Webster had been jailed there! You know I was doing a happy dance at this revelation. But who was Delia Ann Webster you might ask? Let’s take a look at this historically significant woman who was certainly ahead of her time.

Delia Ann Webster (1817-1904)

Delia played such a significant role in not only US History, but also Kentucky history, even though she was not a true Kentuckian. Delia was born in Vergennes, Vermont on December 17, 1817. She was the daughter of Benajah Webster III (1779 – 1851) and Esther Ann Bostwick (1784 – 1870).

Delia was very well-educated, attending the Vergennes Classical School in her home town. By 1835, she held a teaching job in Vermont, but by 1842 she was taking classes at Ohio’s Oberlin College – established as a training school for teachers AND the first college in the U.S. to accept women and African American students.

Reverend Calvin Fairbank (1816 – 1898)

It was at Oberlin College that Delia met fellow student Reverend Calvin Fairbank.

Fairbank was born in New York to a very religious family. After listening to the stories of escaped slaves at Methodist meetings, Fairbank began his abolitionist career in 1837, helping slaves escape along the Underground Railroad. Also during this time, Fairbank was working on his ministry. The Methodist Episcopal Church licensed him to preach in 1840 and ordained him as a minister in 1842. Wanting to continue his education, Fairbank enrolled in Oberlin in 1844.

Oberlin College was, of course, a center of anti-slavery sentiment. Fairbank was already a well-known abolitionist. Delia was from Vermont, also a hot-bed for abolitionists, as central Vermont was a route of the Underground Railroad. It was like a meeting of the minds, I suppose, in the right place, at the right time. Delia and Calvin became friends.

A Move to Lexington, KY

Now, here is where I can’t make events along the timeline make sense. Sometime in 1843, Delia moved to Lexington to co-found a school for young women. (Note that Fairbank didn’t enroll at Oberlin until 1844, but they did meet each other there. So, maybe Delia was traveling back and forth? History is not always crystal clear. There are definitely a few details missing here.) The school she co-founded was named Lexington Female Academy. It is believed that Delia founded the school with fellow friends and teachers, Mr. and Mrs. Spencer. The Spencers later became ill and returned north, leaving Delia to take full charge of the academy. It is believed that Fairbank visited Delia at her boarding house in Lexington in September 1844 with a proposition.

Hayden Family Escape

Fairbank approached Delia with a plan to help the Hayden family escape slavery in Kentucky.

Lewis Hayden (1811 – 1889) was born into slavery in Lexington, Kentucky. As a child, Lewis watched his father, mother, and siblings sold at auction, separating them from one another. Lewis himself had been traded for pair of carriage horses.

Hayden later married Esther Harvey and had two children. One child died early. His wife and remaining child were purchased by statesman Henry Clay, who later sold them down the river. Hayden never saw his wife or child again.

When Hayden later remarried, he had no intention of being separated from his wife Harriet Bell Hayden (1816 – 1893) and her son Joseph. Lewis Hayden, then a waiter at Lexington’s Phoenix Hotel, planned an escape for himself and his family with the aid of Delia Ann Webster and Reverend Calvin Fairbank.

“On Saturday, Sept. 28, 1844 when Lexington was preoccupied with the Fall race horse meets, Webster and Fairbank picked up the Hayden Family and carried them all the way to Maysville, Ky., where the enslaved family was then ferried to Rev. John Rankin at Ripley, Ohio. Rankin was a well known UGR conductor and he continued to help the family to their northward journey.”

Nancy Stearns Theiss / The Courier Journal

A Kentucky Arrest & Conviction

As Delia and Calvin returned to Lexington from Maysville, the two were arrested for aiding and enticing slaves to leave their owners, also known as “slave stealing.” Trials were held for both and both were convicted and sentenced; Delia Ann Webster was sentenced to two years and Reverend Calvin Fairbank to fifteen years (5 years for each individual he helped free). Both would complete their time at the Frankfort State Penitentiary.

Receiving her sentence in December 1844, Delia Ann Webster was the first woman imprisoned for being a part of the Underground Railroad. She was also the only female prisoner at the penitentiary, so she was held in a wooden cottage in the center of the prison yard.

“Nevertheless, the trial jury petitioned Governor William Owsley to pardon Webster because of her sex.  At first, Webster would not accept clemency and demanded a new trial. By the time she warmed to a pardon, public opinion had turned against her and she was carted off to prison in January, 1845.” 

WKU Libraries Blog

While Delia Ann Webster received a “Free and Full” pardon on February 24, 1845, just 5 weeks into her sentence, she was imprisoned long enough to receive the full attention of the married prison warden, Newton Craig. He was enamored by her, and he made sure she knew by writing very scandalous letters to her.

When Delia was released, she returned to Vermont for a few years. During her time there, she wrote a pamphlet called, “Kentucky Jurisprudence: A History of the Trial of Miss Delia A. Webster (1845).” In addition, during this time, she received support of the Northern Abolitionists, who helped fund her return to Kentucky and her continued work of helping the enslaved escape to freedom.

Reverend Calvin Fairbank was pardoned and released in 1849, only completing 4 of his 15 year sentence. Fairbank was arrested just two years later after helping an enslaved man named Tamar escape Kentucky. He was again convicted and sentenced to 15 years in the Frankfort State Penitentiary. He was pardoned again, this time in 1864 by Acting Kentucky Governor Richard T. Jacob.

A Return to Kentucky

With the support and financial backing of the Northern Abolitionists: Norris Day, Parmenas M. Collins and John Preston, Delia returned to Kentucky in 1852. This time she found herself in Milton (Trimble County, KY) where she purchased a 600-acre farm overlooking the Ohio River for $9,000. The deed was recorded in the Trimble County Courthouse on June 6, 1853, purchasing the farm from Willis and Elizabeth Hodge of Louisville. The farm would become a stop on the Underground Railroad. (Milton had already been serving as a major route along the Underground Railroad and an Ohio River crossing destination since 1818.)

The farm, named Mt. Orison, became a “free farm” where freed people were actually paid to work the farm and produce crops. The purpose was to show and prove that hiring workers could be a successful and efficient approach to farming – more so than enslaving workers.

Arrested and Held in the Trimble County Jail

It didn’t take long before local farmers began reporting missing slaves. Delia, of course, became a suspect. In February 1854, the residents of Bedford, KY held a community meeting where they passed a resolution demanding that Miss Delia Ann Webster leave the state.

Of course, she refused and when she did, she was arrested and placed in the Trimble County Jail.

Her stay in the jail was brief as she was released on a technicality. She returned to her farm in Milton, but that stay was brief, too.

In June 1854, Delia was indicted on an issue relating to the 1844 Hayden family Lexington escape. This time, Delia chose to run rather than to be arrested again. She fled across the Ohio River and hid in various Indiana towns. She never returned to Kentucky. Instead she lived in the New England area, Cincinnatti, OH, Madison, IN, and eventually she settled in Iowa after the Civil War. Delia lost ownership of her Milton farm in October 1869. Delia Ann Webster passed away on January 18, 1904 in DesMoines, Iowa. She is buried in the Woodland Cemetery.

Mt. Orison Today

Delia’s farm today has been subdivided, of course. The original home on the farm was burned around 1866 and does not exist today. There were 17 outbuildings on the property that were also burned but were able to be saved. The existing buildings have been remodeled by current owners, and the farm remains a privately owned working farm. Nothing really remains to see or tour from Delia’s time.

Delia Ann Webster’s Long Term Effect

Delia Ann Webster didn’t receive the nickname “The Petticoat Abolitionist” for nothing! It is estimated that Delia helped 100s of enslaved people cross the Ohio River to freedom. She was an extremely brave woman, ahead of her time. Delia did her work at the beginning of the freedom journey, helping with the initial escape, when absences would be quickly noticed. This was not for the faint of heart. This took a level of courage most did not have. While we will likely never know the full effect Delia had on those she helped, we do know about the Hayden family that she helped in 1844.

It is estimated that 500+ enslaved likely crossed the Ohio River in steamboats and river rafts to freedom.

The Long Term effects of the Hayden Family

Lewis and Harriet Hayden were helped to freedom in 1844. Upon their escape, they settled briefly in Canada. In January 1846, the Hayden family moved to Boston, Massachusetts.

“In January of 1846, the Hayden family moved to Boston. The Haydens became key leaders in Boston’s African American and abolitionist communities. Their Beacon Hill Home served as a stop on the Underground Railroad and a gathering place for Boston’s abolitionist movement.”

City of Boston

• Lewis opened a successful clothing shop.
• Between 1850 and 1860, the Haydens sheltered hundreds of people in their home who were running from slavery to freedom.
• Lewis and Harriet became involved in formal organizations fighting to end slavery.
• Once the Civil War began, Lewis began recruiting African Americans for Massachusetts 54th regiment. Three regiments of black soldiers ultimately represented Massachusetts in the Civil War, most of which were recruited by Lewis.
• Lewis became the first black man elected to the Massachusetts Legislature in 1873.
• Lewis dies in 1889, and Harriet in 1893. Upon Harriet’s death, their estate was donated to Harvard Medical School to establish The Lewis & Harriet Hayden Scholarship for Colored Students. That scholarship continues to be given today.
• The Lewis and Harriet Hayden House is listed as a National Historic Site and is a part of the Black History Trail. It is a privately owned home and is not open for tours.

A Memorial to the Haydens in Lexington, KY

As I worked on my research for this article, I was shocked to come across the Lexington Freedom Train project. Not because of the project, but because of the timing. Again, it was like God grabbed my hand and said, now is the time to write this. Remember, I just learned of Delia Ann Webster this past Summer and visited the Trimble County Jail this past Fall. I didn’t learn of the Haydens until yesterday! As I dug for more information, I stumbled upon an article written by the University of Kentucky in June 2024. The article explained how a new monument is set to be unveiled in June 2025 – a new monument dedicated to Lewis and Harriet Hayden. Seriously, as I sit here writing this, I have goosebumps. The timing is just something I can’t explain.

In June 2025, a beautiful sculpture is set to be revealed on the southeast corner of North Limestone and Fourth Streets in Lexington on the property of the Lexington Traditional Magnet School. The monument is to be titled Lexington Freedom Train, but it represents Lewis and Harriet and celebrates the path they courageously took to freedom. The bronze statue will be an impressive 8 feet tall, sitting upon an impressive 40″ x 66″ x 24″ granite base.

So, while there is nothing in Kentucky at the moment to tell of these two courageous individuals, there will be soon, and I couldn’t be more excited to learn about it! Of course, as soon as it is unveiled, I’ll make the trip to see this amazing work of art and you’ll get to see it, too!

My Visit to the Trimble County Jail

Nothing exists in Kentucky today to memorialize Delia Ann Webster, either. If it weren’t for the Old Trimble County Stone Jail, I wouldn’t be telling this history at all. That’s the downside of only bringing you the history of the places that still exist today. When we lose the places, we often lose the history, too. That explains my passion for historic preservation! I could get on a soap box and go on and on, but I won’t. Instead, I’ll tell you that the Trimble County Jail was built in 1850 on the foundation of a previous jail. Only the first story was built at the time. In 1899, the second story was added, with only an exterior set of stairs to access it. The building was used until 1983! When you see my photos below, you’ll wonder how it was possible that it was still in use in the 80s.

On this particular day, I pulled into Bedford and parked just across from the jail. The iron gate surrounding the jail was unlocked, and I saw two men working on the backside of the jail. I cautiously walked over to the men and asked if I could sneak a peek inside. I was directed to the Jailer’s Office to ask permission. I was pleased to receive it and took a few minutes (that’s all that was needed) to explore the interior of the first floor where Delia Ann Webster was imprisoned. I then ventured up the exterior stairs, but the rust and holes along the steps made me rethink that decision quickly. I stopped on the landing, snapped one picture of the 2nd floor, and hustled myself back down the stairs.

Interior Photos of the Old Stone Trimble County Jail. The last photo is of the second floor. / All Photos Courtesy of KHT

I thanked the two men for their time (they had plugged in a light for me to take photos) and went on over to the courthouse to take a few photos there. There wasn’t much else to do, so I got back in the car and headed on down the road to New Castle. The 22 minute drive along US-421 between the two towns was absolutely gorgeous, and I wished that I had visited a few weeks earlier to see the peak of Fall color. That’s a drive that is absolutely beautiful, and I would love to make it again some day!

My Reflection

I feel like I’ve said quite a bit already, so I’ll try to make my reflection short and sweet. First, we are so very lucky that the Trimble County Stone Jail still stands. There are a few other stone jails that still stand in Kentucky today, but we have lost a few. If we didn’t have the Trimble County Jail, I wouldn’t have had the chance to tell Delia’s story, along with Calvin’s and the Haydens’. I hope more people become aware of Delia’s story. Maybe that will lead to a monument for her. We’ll never know who all she helped and what those people went on to do with their lives, but the Haydens are an amazing example of the positive impact we know she had. Just think of that story multiplied by 100 – at least! Delia definitely deserves to be remembered, and something to commemorate her work is the least we could do!

How incredible is it that just as I learn of the Haydens, a monument is in the works for them in Lexington? Their story will officially leave the shadows and be brought into the light. It will be a place to stand and celebrate them, along with their strong dedication and bravery to what was right, when doing right was hard. We are certainly on the right road with this project.

I hope more of these stories will come to light. The more time that passes, the more likely that history will be lost, but I’ll keep doing what I’m doing… bringing it to you when I discover the people and places of our past!

I truly hope you enjoyed this history of Delia, Calvin, and the Haydens!

Until next time… Happy Travels!