Kentucky's Divided Role in the Underground Railroad

Border state's geography and conflicting loyalties made it a critical yet dangerous gateway to freedom

Published on Feb. 16, 2026

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Kentucky's unique position as a border state during the Civil War era made it a crucial yet complex part of the Underground Railroad network. While its location along the Ohio River provided opportunities for enslaved people to escape to free states to the north, the state's divided loyalties between pro-slavery and anti-slavery factions created a dangerous environment for those seeking freedom. The story explores the role of key figures like abolitionist John Rankin and conductor Arnold Gragston, as well as the complicated relationship of some slaveholders like Jack Tabb, in enabling and hindering the Underground Railroad in Kentucky.

Why it matters

Kentucky's position as a border state with both slave-holding and abolitionist elements highlights the nuanced and often contradictory nature of the Underground Railroad. Its geography made it a critical gateway to freedom, but its internal divisions created a volatile environment that put freedom seekers at great risk. Understanding this complex history provides insight into the challenges and dangers faced by those fighting for emancipation.

The details

Kentucky's location along the Ohio River, which formed the border between slave states to the south and free states to the north, made it a prime location for the Underground Railroad. Towns like Maysville served as key crossing points, with abolitionist figures like John Rankin in nearby Ripley, Ohio providing aid and safe passage. However, Kentucky also had a strong pro-slavery faction, leading to a divided loyalty that put freedom seekers in constant danger. Enslaved conductor Arnold Gragston recounted the risks he took to row escapees across the river, often narrowly evading capture by his own enslaver, Jack Tabb, who had a complicated relationship with slavery.

  • In 1831, the story of Tice Davids escaping across the Ohio River from Kentucky is believed to have inspired the term 'Underground Railroad'.
  • Arnold Gragston worked as a conductor on the Underground Railroad for four years, starting around 1859.
  • In 1863, Gragston helped around 12 freedom seekers cross the Ohio River in a single night, leading to an intense pursuit that forced him to go into hiding.

The players

John Rankin

A Presbyterian minister in Ripley, Ohio who was a prominent abolitionist, operating an Underground Railroad station and providing aid to freedom seekers crossing the Ohio River from Kentucky.

Arnold Gragston

An enslaved man in Mason County, Kentucky who worked as a conductor on the Underground Railroad for four years, helping an estimated 200-300 people escape to freedom in Ohio.

Jack Tabb

A Kentucky slaveholder who had a complex relationship with slavery, at times allowing his enslaved people unusual freedoms and even assisting in their escapes, while also physically punishing them.

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What they’re saying

“I don't know to this day how he [Tabb] never knew what I was doing; I used to take some awful chances, and he knew I must have been up to something; I wouldn't do much work in the day, would never be in my house at night, and when he would happen to visit the plantation where I had said I was goin' I wouldn't be there. Sometimes I think he did know and wanted me to get the slaves away …”

— Arnold Gragston, Formerly enslaved conductor on the Underground Railroad (Federal Writers' Project: Slave Narrative Project)

“The only way I knew who they were was to ask them 'What you say?' And they would answer, 'Menare.' I don't know what that word meant — it came from the Bible. I only know that that was the password I used and all of them that I took over told it to me before I took them”

— Arnold Gragston, Formerly enslaved conductor on the Underground Railroad (Federal Writers' Project: Slave Narrative Project)

What’s next

Historians continue to research Kentucky's complex role in the Underground Railroad, uncovering new stories and perspectives that shed light on this critical chapter of American history.

The takeaway

Kentucky's position as a border state with divided loyalties highlights the nuanced and often contradictory nature of the Underground Railroad. Its geography made it a vital gateway to freedom, but its internal tensions also put escapees at great risk, underscoring the bravery and ingenuity of those who fought for emancipation.