At a Glance
Vermont to Lexington: A Northern Woman in Slave Territory
The decision to go south and teach was, for many educated Northern women of the 1840s, primarily an economic one — the South's shortage of trained teachers created professional opportunities that the more competitive Northern market could not match, and the social respectability of the schoolteacher's role made it an acceptable form of employment for women of the middle class. But for Delia Webster, the decision to go to Kentucky was not purely economic. She was already engaged with antislavery ideas when she arrived in Lexington, already connected to the network of reformers and activists that the abolitionist movement was developing in New England, and the position she established in Lexington was, at least in part, a position from which she could observe slavery at close range and find ways to act against it.
Lexington, Kentucky, in the early 1840s was a city that prided itself on its relative sophistication and cultural development — it had been called the Athens of the West in the early republic, and it maintained a self-image as a centre of education, culture, and gentility that distinguished it from the rougher frontier settlements of the deeper South. But the gentility of Lexington's white social world was underwritten by slavery. The horses and the hemp and the tobacco that made the Bluegrass region prosperous were produced by enslaved labour, and the domestic comfort of Lexington's white households depended on the unpaid work of enslaved domestic workers. The slave markets operated openly, and the human beings sold there were as visibly a part of the city's commercial life as the horses that its owners took such pride in breeding.
Webster ran the Lexington Female Academy and occupied a position in the white social life of the city that was unusual for a Northern woman — she was accepted, at least to a degree, as a respectable professional woman whose presence in the community was valuable. This acceptance gave her the mobility and the social cover that made her collaboration with Calvin Fairbank possible. Fairbank was a stranger in Lexington, identifiable as a Northern abolitionist by his manner and his associations; Webster was an established figure whose movements attracted less suspicion and whose access to the networks through which information about potential escapees circulated was considerably greater than his.
The Hayden Rescue: What They Did and What It Cost
Lewis Hayden had been enslaved in Lexington for years, and his desire to escape was connected in the most personal way to the worst that slavery could do — his enslaver had sold his first wife and child, and the threat that the same would happen to his second family hung over him constantly. His connection to Webster and Fairbank is not fully documented, but the rescue operation that the three of them — along with Harriet Hayden, who was a full participant in the escape — managed to pull off in September 1844 was one of the more logistically complex operations in the Underground Railroad's record in Kentucky.
Webster's specific contribution to the rescue has been a matter of some debate. At her trial, she denied knowing that the purpose of the carriage journey she took with Fairbank and the Haydens was to facilitate an escape, and this denial was almost certainly false — the trial record and the subsequent accounts of the operation make it clear that she was a knowing participant. What is less clear is precisely what she did: whether she provided transportation, cover, safe-house space, or some combination of these. What is clear is that the operation succeeded, that Lewis Hayden and his family reached freedom, and that Webster was caught on her return, identified, arrested, and tried alongside Fairbank.
The consequences for Webster were substantially less severe than for Fairbank, whose fifteen-year sentence reflected the court's assessment of his greater culpability and possibly its greater hostility to a Northern man who had come into Kentucky specifically to undermine its social order. Webster's two years, and the month she actually served before being pardoned, might seem lenient by comparison — but for a woman of her background and social position, the very fact of arrest, trial, and conviction was a profound humiliation and a permanent alteration of her social identity. She was no longer simply a schoolteacher; she was a convicted slave-stealer, a woman who had been imprisoned by the state of Kentucky, a figure of controversy whose subsequent activities would be watched with suspicion by the authorities of whatever state she operated in.
The Published Account and the Politics of Respectability
Webster's response to her conviction was to write about it, and the pamphlet she published in 1845 — "Kentucky Jurisprudence: A History of the Trial of Miss Delia A. Webster" — was an effective piece of abolitionist propaganda precisely because of the position from which it was written. A male Underground Railroad conductor imprisoned in Kentucky was a hero of the movement, but he was also, in the eyes of much of the Northern public, someone who had voluntarily entered dangerous territory and paid the expected price. A female schoolteacher imprisoned in Kentucky for the same activities was something different — a figure of respectability and social innocence who had been subjected to the full coercive power of the slave state, and whose imprisonment was therefore a more viscerally effective demonstration of the slave system's willingness to imprison Northern citizens for the exercise of their moral convictions.
The pamphlet circulated widely in the Northern antislavery press and contributed to the public understanding of what the slave power was willing to do to its opponents. It positioned Webster as a victim of Southern legal tyranny rather than as a defiant activist who had chosen her fate, which was a somewhat misleading framing but an effective one for reaching audiences who were sympathetic to antislavery but not yet committed to the kind of direct action that Webster had actually taken. It helped establish the narrative of Northern victimisation by Southern legal violence that would be a recurring element in abolitionist rhetoric throughout the 1840s and 1850s.
Return to Kentucky and the Vision of an Antislavery Colony
The most remarkable and least understood aspect of Delia Webster's career is what she did after her pardon and her return to Vermont — which was, eventually, to go back to Kentucky. The decision to return to a state that had imprisoned her, surrounded by a community that regarded her with deep hostility, in pursuit of a project that had no realistic chance of success, requires some explanation. The explanation that Webster herself gave was religious and moral — she believed that the best way to challenge slavery was not to agitate against it from a safe Northern distance but to demonstrate within slave territory that the free-labour alternative was economically viable, socially functional, and morally superior.
The farm she established in Trimble County, Kentucky, in the early 1850s was designed as a model of free-labour agriculture — an enterprise that would grow its own food, employ free workers, and demonstrate by its success that the Southern argument for slavery's economic necessity was false. She also hoped, more ambitiously, to create a community that could serve as a way station for escaped slaves and eventually as a base for a broader transformation of the region's social and economic structure.
The project was, by any external measure, a failure. Her neighbours were hostile, the state authorities were watching, and the combination of economic difficulty and social isolation made the farm nearly impossible to sustain. She was arrested again in 1854 on charges related to her Underground Railroad activities and spent time in jail before the charges were eventually dropped. But she persisted, maintaining some presence in Kentucky through the 1850s and eventually establishing a more permanent residence there after the Civil War, staying in the state where she had made her stand even when the cause that had brought her there had been formally won.
Long Life, Slow Forgetting, and the Recovery of a Difficult Legacy
Delia Webster lived to eighty-seven — an extraordinary lifespan for a woman of her generation — and died in 1904, the last surviving member of the small group who had rescued Lewis Hayden from slavery in Lexington in 1844. Hayden himself had died in 1889; Calvin Fairbank had died in 1898. She outlived them all, dying in the Kentucky that had imprisoned her, on the farm that had been the site of her most stubborn and ultimately most futile act of resistance.
Her story presents interpretive challenges that may help explain why it has received less attention than the stories of more straightforwardly heroic abolitionist figures. Her denial of knowing that the Hayden journey was an escape attempt — a denial she maintained at trial even though it was almost certainly false — complicates the picture of her as a straightforward martyr for truth. Her subsequent return to Kentucky, with its combination of genuine moral courage and questionable judgment about what was actually achievable, was a career move that attracted both admiration and bewilderment from contemporaries who could not quite decide what to make of a woman who voluntarily placed herself in such danger for such uncertain ends.
What is not in question is the significance of what she did in September 1844, and of what Lewis Hayden did with the freedom she helped him claim. The Boston that Hayden built his career in — the Boston of resistance to the Fugitive Slave Act, of the 54th Massachusetts Regiment, of Frederick Douglass's lectures and William Lloyd Garrison's Liberator — was a Boston that was partly the product of the rescue that Webster and Fairbank had organised in a Kentucky carriage on a September night. That is a legacy worth recovering, even if the woman who helped create it remains difficult to fully understand.