Lexington History & Civil War Heritage Record • National Network to Freedom
The Clandestine Bluegrass: Lexington’s Secret Freedom Highway
During the Antebellum and Civil War eras, Lexington, Kentucky stood as a tragic paradox: the commercial center of the Bluegrass and one of the largest domestic slave-trading hubs in the American Upper South at Cheapside, and simultaneously one of the most daring launching grounds for the Underground Railroad. Because Kentucky was a Union border slave state where the Emancipation Proclamation did not legally apply, freedom could only be won through perilous flight—either northbound across the Ohio River or southbound to Union military lines at Camp Nelson. Anchoring this secret network was Historic St. Paul A.M.E. Church, situated just blocks from today’s Rupp Arena, which concealed an architecturally hidden loft behind its sacred pulpit where freedom seekers were sheltered before embarking on the midnight run.
Part 1: The Regional Escape Routes Across Kentucky (Macro Map)
Escaping from the heart of the Bluegrass required navigating hostile terrain dominated by slave patrols, tollgate keepers, and armed slave catchers. Freedom seekers and conductors developed four primary corridors radiating out of Lexington:
Kentucky • Ohio River Freedom Corridors
Vector Cartography • Central Kentucky Hub
River Crossing: Maysville to Ripley, OH.
Conductors: Rev. John Rankin, John Parker.
Significance: The route taken by Lewis and Harriet Hayden on their daring 1844 midnight carriage escape.
River Crossing: Covington/Newport to Cincinnati.
Conductors: Levi Coffin (“President of the UGRR”).
Significance: High-traffic path moving freedom seekers directly into Cincinnati’s abolitionist network.
Destination: Camp Nelson National Monument.
Key Law: Federal Enlistment Act of 1864.
Significance: Freedom ran south. Over 10,000 enslaved men marched south to enlist in the USCT.
River Crossing: Falls of the Ohio to New Albany, IN.
Conductors: Black maritime ferrymen.
Significance: Westbound river route connecting to Indiana safe havens.
Part 2: The Church Near Rupp Arena: Secret Rooms Behind the Pulpit
Visitors walking through downtown Lexington along West Vine or High Street past Rupp Arena and Central Bank Center often remain unaware that they are standing within footsteps of the underground nerve center of Kentucky resistance. Two iconic congregations anchored this quadrant:
Historic St. Paul A.M.E. Church (251 N. Upper Street)
Established in 1820 with its historic red-brick sanctuary erected in 1826, St. Paul A.M.E. Church is one of the oldest continuously operating African American sanctuaries in the Commonwealth of Kentucky. It was officially verified and enrolled by the National Park Service into the National Underground Railroad Network to Freedom due to verified physical architectural evidence:
- The Concealed Pulpit Staircase & Loft: Concealed directly behind the sacred pulpit altar was a narrow, twisting wooden stairway that ascended into an unventilated 6 × 10 foot false ceiling loft. Freedom seekers were sequestered in this cramped space during daylight hours while regular worship or community activities occurred below.
- Counter-Surveillance Dog Diversion: Church oral histories and records document that the congregation acquired an adjacent municipal stray animal holding pen. The intense smell of the animals was deliberately used to overwhelm and confuse the tracking bloodhounds deployed by Lexington slave catchers.
- Abolitionist Nexus: Famed abolitionist Lewis Garrard Clarke—whose autobiography inspired the character George Harris in Harriet Beecher Stowe’s Uncle Tom’s Cabin—preached here later in life, and his 1897 funeral was held within this sanctuary.
Historic Pleasant Green Missionary Baptist Church (540 W. Maxwell Street)
Tracing its roots back to 1790, Pleasant Green is recognized as the oldest active Black congregation west of the Allegheny Mountains. Founded by enslaved preacher Peter Duerett (known reverently as “Brother Captain”), the church purchased its Maxwell Street ground in 1822. Located directly adjacent to Patterson Street and the railroad tracks behind Rupp Arena, the church provided critical food, safe shelter, and spiritual fortitude to freedom seekers slipping through the railroad switches.
Part 3: Downtown Lexington Safe Havens & Hotspots (Street Grid Map)
Explore the physical geography of resistance and the slave trade in downtown Lexington. Rupp Arena, the historic churches, the Cheapside auction block, and getaway points all sit within a 15-minute walking radius:
Downtown Lexington • Civil War Era Hotspots Map
Rupp Arena to Upper Street Corridor
1. Historic St. Paul A.M.E. Church • 251 N. Upper Street (Network to Freedom Site)
Walking Distance from Rupp Arena: ~6 blocks (0.5 miles, 10 min walk).
The Secret Architecture: Behind the church’s pulpit sits a narrow winding staircase leading up to an unventilated 6×10 foot loft between the sanctuary ceiling and the roof. Freedom seekers lay in silence above Sunday sermons while waiting for nightfall.
The Dog Diversion: Church elders acquired a city stray animal pen next door to confuse the bloodhounds of Lexington slave catchers.
2. Historic Pleasant Green Missionary Baptist Church • 540 W. Maxwell Street
Walking Distance from Rupp Arena: 2 blocks south (0.2 miles, 4 min walk).
Historic Roots: Founded in 1790 by enslaved preacher Peter Duerett (“Brother Captain”), making it the oldest active African American congregation west of the Alleghenies. Situated right along the railroad tracks and Patterson Street corridor, the congregation provided essential sanctuary, provisions, and concealment.
3. Cheapside Slave Auction Block • Henry A. Tandy Centennial Park (Main & Upper)
Walking Distance from Rupp Arena: 3 blocks east (0.3 miles, 6 min walk).
The Auction Block: Cheapside was the largest slave trading market in Kentucky and one of the most notorious in the American South. Thousands of enslaved men, women, and children were sold away from their families “down the river” to the cotton plantations of the Deep South. The horror of Cheapside was the primary catalyst driving Lexington freedom seekers to risk death on the Underground Railroad.
4. The Lewis & Harriet Hayden Getaway Rendezvous • High & Patterson Corridor
Walking Distance from Rupp Arena: Immediately adjacent to Central Bank Center.
The 1844 Escape: On the stormy evening of September 28, 1844, Rev. Calvin Fairbank and Delia Webster pulled up a hired two-horse carriage at this corner to load Lewis Hayden, his wife Harriet, and their son Joseph before galloping north up the Maysville Road.
5. Main Street Baptist Church & Mary Todd Lincoln House • 582 W. Main Street
Walking Distance from Rupp Arena: Directly opposite Rupp Arena across Main Street.
Civil War Convergence: Main Street Baptist Church was organized in 1862 amidst the Civil War directly across the street from the childhood home of First Lady Mary Todd Lincoln, representing the courageous creation of autonomous Black religious leadership.
6. Cassius M. Clay’s Anti-Slavery Press • North Mill Street
Walking Distance from Rupp Arena: 4 blocks northeast (0.4 miles, 8 min walk).
Fortified Abolition: In 1845, fiery abolitionist Cassius Marcellus Clay published The True American from this office. To defend the press against pro-slavery lynch mobs, Clay fortified the brick building with sheet-iron doors, two brass four-pounder cannons loaded with grapeshot, and ten Mexican lances.
Part 4: The Daring Midnight Ride of Lewis & Harriet Hayden (1844)
Of all the escapes launched from Lexington, none reverberated across the nation more profoundly than that of Lewis Hayden, his wife Harriet, and their young son Joseph.
Enslaved in Lexington and hired out as a waiter at the Phoenix Hotel on Main Street, Lewis Hayden watched in horror as his first wife and children were sold away at the Cheapside auction block. Vowing never to let enslavement destroy his family again, Hayden allied with two white abolitionists: Rev. Calvin Fairbank, an impassioned Methodist minister from New York, and Delia Webster, a Vermont teacher who co-founded the Lexington Female Academy.
The Flour-Dusted Disguise on the Maysville Road
On the rainy night of September 28, 1844, Fairbank and Webster hired a carriage from a Lexington livery stable. They rendezvoused with the Haydens near Patterson Street, dusting the family’s faces with white flour and veiling them as a traveling white family to pass through tollgates along the Maysville Road. Driving relentlessly through Paris and Washington, they covered 65 miles by dawn, reaching the banks of the Ohio River at Maysville. There, they crossed into Ripley, Ohio, where free Black abolitionist John Parker and Presbyterian minister John Rankin ushered them into the underground pipeline.
Upon returning to Lexington, Fairbank and Webster were arrested. Delia Webster was sentenced to two years in the Kentucky State Penitentiary—becoming the first woman imprisoned for aiding runaway slaves in Kentucky—while Fairbank served nearly two decades in prison. The Haydens settled in Boston, Massachusetts, transforming their Beacon Hill residence into one of the most famous and heavily fortified stations on the national Underground Railroad.
Part 5: When Freedom Ran South: The Civil War & Camp Nelson (1863–1865)
The defining irony of the Civil War in Kentucky occurred in 1864. While the Underground Railroad had spent decades pointing enslaved people toward the North Star, the battlefield suddenly inverted the compass: freedom ran south.
In 1864, the federal government authorized the recruitment of African American soldiers in Kentucky into the United States Colored Troops (USCT). Just 18 miles south of Lexington along the Kentucky River palisades stood Camp Nelson. Under federal statutory law, any enslaved man who enlisted in the Union Army was granted immediate, irrevocable freedom. In March 1865, Congress expanded this decree to include the soldiers’ wives and children.
Enslaved men from Lexington and surrounding Fayette County farms walked out in broad daylight or slipped away at night, daring white slave patrols to intercept them before they reached the federal ramparts of Camp Nelson. Their service proved decisive in crushing Confederate rebellion in Kentucky, Tennessee, and Virginia.
How to Visit & Experience Lexington’s Underground Railroad Sites Today
If you are walking in downtown Lexington near Rupp Arena or exploring the Bluegrass, here is how you can retrace these pivotal sites: