Appalachian History
On most Civil War maps, northeastern Kentucky sits in the margin, tucked between the Big Sandy Valley and the Ohio River. The names that dominate the chapter headings are far away: Shiloh, Antietam, Vicksburg. Yet along the riverfront streets of Greenupsburg, in the hill farms on the Little Sandy, and on the roads that led south toward the Cumberland Gap, the war pressed hard on Greenup County.
Before the Civil War, Greenup County had already witnessed a dramatic act of enslaved resistance. On August 14, 1829, near present day Lynn, a coffle of enslaved people being forced south revolted, killing two traffickers. Sixteen attempted to escape, but all were later recaptured. During the war, local Unionists filled the ranks of the 22nd Kentucky Infantry at Camp Swigert, while the same riverfront received thousands of exhausted soldiers who had just marched nearly two hundred miles out of the Gap. After Appomattox, men who had learned to fight as home guards and guerrillas turned those skills on one another along the Carter–Greenup line, leaving the region a lingering war zone long after formal peace.
Greenup County’s Civil War story is not a tale of a single big battle. It is instead a river county’s view of a border war: enslaved resistance, recruiting camps, mountain retreats, guerrilla raids, and postwar feuds that grew from habits formed during four hard years.
A River County Before the War
On the eve of the 1850s, Fanning’s Illustrated Gazetteer described Greenup County as a hilly, broken corner of Kentucky, wedged between the Ohio River on the north and northeast and the Sandy River on the southeast. The seat of justice was Greenupsburgh and the county’s population climbed from 4,311 in 1820 to 9,654 by 1850. River landings and iron furnaces tied Greenup as much to Ohio and western Virginia as to the Bluegrass. Flatboats and steamboats carried iron from furnaces like Hunnewell and Greenup Furnace, along with timber, grain, and people, through what was then still a young industrial corridor.
Slavery existed here, but on a smaller scale than in central Kentucky. The Notable Kentucky African Americans Database counts 89 slaveholders in Greenup County in 1850, with 248 Black and 114 mulatto enslaved people, along with 34 free Black residents in the decades around the war. The numbers are modest compared to plantation counties, but they remind us that the Ohio’s northern shore did not magically erase bondage. Instead, Greenup sat on a border where slavery and antislavery politics collided.
The Greenup Slave Revolt of 1829
More than three decades before Fort Sumter, Greenup County saw one of the most striking episodes of enslaved resistance in the region. On August 14, 1829, a coffle of enslaved men, women, and children being force-marched south rose up near the banks of Tygarts Creek. In the struggle, two traffickers were killed, and sixteen people broke away in an attempt to escape. All of the escapees were eventually recaptured.
Appalachian Freedom Heritage Tourism Initiative research ties the revolt to a forced migration route that carried enslaved people toward the lower South slave markets. The site’s documentation traces the court proceedings that followed in Greenup County, including death sentences for several defendants and executions near Greenup in November 1829, with one woman, Dinah, later receiving a gubernatorial pardon in 1830.
This revolt also appears in abolition-era print culture. Appalachian Freedom notes that the uprising was referenced by abolitionist David Walker in his 1829 Appeal, and argues that the episode helped shape Kentucky debates that later produced the state’s Non-Importation Act of 1833. In the present day, the event has gained formal recognition through the National Park Service. On May 1, 2025, the Greenup County Slave Revolt Site was added to the National Underground Railroad Network to Freedom Program.
Greenup also appears in Underground Railroad lore. In The Underground Railroad from Slavery to Freedom, Asbury Parker, who had fled bondage in Greenup County, told of crossing into Ohio in a suit of fine broadcloth, clothing he thought proper for a free man. Between revolt, escapes, and day-to-day survival, Black life in the county shaped the local politics of loyalty and fear long before 1861.
A Union Stronghold on the Ohio
When war finally came, Greenup tilted decisively toward the Union. The Kentucky National Guard’s compilation The Paper Trail of the Civil War in Kentucky, drawing on The Kentucky Encyclopedia and Nina Biggs and Mabel Mackoy’s History of Greenup County, bluntly labels the county a Union stronghold.
Eastern Kentucky and the Civil War, a research blog grounded in local records, estimates that at least eight hundred Greenup County men enlisted in Union regiments. Only a few dozen are known to have joined Confederate units. Judge W. S. Seaton, reporting to the adjutant general in 1864, counted just twenty-three men from the county in Confederate service.
That does not mean the county was free of secessionist activity. In 1861, Dr. William S. Kouns raised a pro-Southern state guard company, and a small cluster of Greenup men slipped south to join mounted Confederate units. But the center of gravity leaned firmly toward the United States. Home guards formed along the river, farmers drilled on courthouse squares, and the county’s river landing at Greenupsburg soon hosted one of Kentucky’s early Union recruiting camps.
Camp Swigert and the 22nd Kentucky Infantry
In late 1861, Union authorities established a recruiting and training camp on bottomland near the Ohio River in the Greenupsburg area. The site offered what the army needed: flat ground, access to roads, and the deep, steady water of the Ohio for steamboats bringing supplies and recruits.
Historical Marker #2247 and the Kentucky Legislative Research Commission summary describe Camp Swigert as a Union recruiting camp that was organized in December 1861, when the 22nd Kentucky Union Infantry Regiment formed there. Recruits came from Greenup and surrounding counties, and also from Louisville. The regiment was mustered into United States service in early January 1862.
Soon after organizing, part of the 22nd fought at the Battle of Middle Creek near Prestonsburg, where contemporary accounts and later summaries credit their charge with helping turn the fight. After that, the regiment’s path led away from their home county. The 22nd manned the heights of Cumberland Gap, guarded supply lines in the mountains, and eventually marched west into major campaigns in the Mississippi Valley.
For Greenup families, that horror began not in Mississippi but in a camp on the riverbank. Muster rolls compiled by Biggs and Mackoy, and now echoed in genealogical databases, show clusters of local surnames in the 22nd and other Union regiments. Camp Swigert turned a small Ohio River town into one of northeastern Kentucky’s most important Union training grounds.
Nine Thousand Men on the Road
The largest single military movement to touch Greenup County did not start there. It began high in the Cumberland Gap in June 1862, when Union brigadier general George W. Morgan occupied the vital mountain pass with roughly nine thousand men. Confederate operations soon cut his supply line, making the position untenable.
In mid-September, Morgan abandoned the Gap and led his column north across the mountains. Over the next sixteen days, his men trudged more than two hundred miles along rough roads and river valleys, harassed by Confederate cavalry. When the retreat ended, about eight thousand of Morgan’s soldiers reached Greenup on October 3, 1862, on the way toward Camp Dennison near Cincinnati.
For local residents, the arrival must have been overwhelming. In Greenup, the courthouse square, river landing, and nearby farms would have been crowded with tents, wagons, exhausted soldiers, and sick men waiting for transport up the river. County histories compiled in the twentieth century, drawing on family stories, portray the retreat as a moment when the war suddenly became impossible to ignore.
Guerrillas on the Border
Union control of Greenup County did not end the fighting. Like many border counties in Kentucky, Greenup and its neighbors experienced a chronic guerrilla problem as the war dragged on. Armed bands, some loosely attached to regular Confederate units and others simply criminal, moved through the hills stealing horses, robbing stores, and targeting outspoken Unionists.
Eastern Kentucky and the Civil War’s essay on Cook’s Guerrillas traces the activities of Captain George “Dave” Cook and his men across northeastern Kentucky and the Ohio borderlands. Drawn from the Official Records and period newspapers such as the Ironton Register and Louisville Journal, the narrative shows Cook’s band raiding across the river near Ashland, robbing households and stores, and skirmishing with Ohio cavalry detachments.
One of the incidents the blog highlights occurred in Greenup County near Oldtown, where Cook’s men wounded Jarred Biggs, a local Unionist, during a July 1863 raid. News of such attacks traveled quickly along the Ohio. Editors north of the river warned that guerrillas might use Kentucky as a launching pad for raids into Ohio towns.
Greenup’s Union home guards and militia tried to respond. Some of the same men who saw Morgan’s retreat in 1862 later scouted back roads and river crossings in search of guerrillas. Those habits of armed self-defense did not vanish in 1865.
Violence After Appomattox
Historian James M. Prichard titled his study of northeastern Kentucky in the late 1860s and 1870s “Lingering War Zone,” a phrase that fits the region’s experience. Drawing on Carter and Greenup County court records, local newspapers, and gubernatorial correspondence, Prichard traces how former Union and Confederate partisans carried wartime grudges and guerrilla tactics into postwar feuds.
The most notorious episode unfolded along the Carter–Greenup line in the so-called Underwood War. During the war, the Underwoods had led a Tygart Valley home guard company that fought Confederate raiders. In an 1877 newspaper interview quoted by Prichard, Jesse Underwood insisted that their home guards had blocked rebel guerrillas from reaching towns like Portsmouth, Ohio.
By the 1870s those same men were at the center of a rolling series of ambushes, barn burnings, and sieges that pitted the Underwoods and their allies against neighboring families and later against vigilantes styling themselves Regulators. The Underwood cabin, fortified during the war with loopholed upper walls and shuttered ground-floor windows, stood as “Fort Underwood” in press reports. State troops eventually surrounded the place more than once.
For Greenup County, that meant the wartime line between Unionist and rebel neighbors never entirely healed. The region’s later reputation for feuding cannot be separated from the guerrilla warfare and home guard organizing that spread through its hills after 1861.
Who Served, Who Stayed, Who Resisted
The county’s demographic and service patterns underline the complexity of its Civil War experience. The NKAA database’s tally of slaveholders and enslaved people shows how slavery threaded through riverfront businesses and farms, even in a place with relatively small holdings. The Greenup County Slave Revolt, now documented through Appalachian Freedom’s research and recognized by the National Park Service’s Network to Freedom program, offers a rare, detailed record of enslaved people in the region choosing violent resistance rather than submission.
On the military side, the Eastern Kentucky and the Civil War blog’s estimate of at least eight hundred Union soldiers from Greenup County is backed up by the rosters printed in Biggs and Mackoy’s History of Greenup County and by compiled military service records. Dozens of those men served in the 22nd Kentucky organized at Camp Swigert, but others joined neighboring infantry and cavalry units.
Only a handful of Greenup natives appear in Confederate muster rolls. That imbalance helps explain why local memory and modern markers emphasize Union service, from Morgan’s retreat to the 22nd’s early combat at Middle Creek.
Reading Greenup’s Civil War Today
For a county often left out of big Civil War narratives, Greenup is unusually well documented if you know where to look. The Kentucky Historical Society maintains key markers in Greenup that frame the story, including marker 2247 for Camp Swigert and marker 520 for A Masterful Retreat on the courthouse lawn.
The Civil War Governors of Kentucky Digital Documentary Edition lets researchers filter petitions, letters, and official documents by county, turning up correspondence about Greenup soldiers and wartime local issues. The Paper Trail of the Civil War in Kentucky and the Kentucky National Guard’s online history summarize the county’s wartime role and point back to Biggs and Mackoy’s mid-century county history for rosters and anecdotal detail.
To read the deeper prewar story of freedom seeking and resistance, Appalachian Freedom’s Greenup Slave Revolt page offers a detailed narrative rooted in court records and gubernatorial materials, while the National Park Service’s Network to Freedom announcement provides a concise federal summary of the revolt and its recognition.
Why Greenup’s Story Still Matters
Greenup County’s Civil War era captures many of the tensions that defined the Appalachian borderlands. A modest slaveholding county sent an overwhelming share of its white men into Union ranks. In 1829, enslaved people being marched through Greenup County rose up near Tygarts Creek in a desperate bid for freedom, an event now formally recognized through the National Underground Railroad Network to Freedom. A quiet river town briefly became a major Union recruiting center and then the destination of one of the war’s most demanding retreats. Guerrillas haunted its back roads and, after the soldiers went home, their methods helped shape feuds that made national headlines.
When you stand today on the courthouse lawn at Greenup and read the Masterful Retreat marker, it is worth remembering not only the thousands of worn-out Union soldiers who passed through town in 1862, but also the enslaved people who broke free from their chains in 1829, the volunteers who drilled at Camp Swigert, the guerrillas who crossed and recrossed the river, and the families who lived with the long shadow of that conflict for decades afterward.
Sources and Further Reading
Official Records of the Union and Confederate Armies (reports on Cumberland Gap operations, Morgan’s retreat, and guerrilla activity in northeastern Kentucky).
National Park Service, “National Park Service Adds 31 New Listings in 13 states to the National Underground Railroad Network to Freedom Program,” News Release dated May 1, 2025, including the Greenup County Slave Revolt Site entry.
“The Greenup Slave Revolt,” Appalachian Freedom Heritage Tourism Initiative, with documentation of the 1829 uprising, trials, and aftermath.
Wilbur H. Siebert, The Underground Railroad from Slavery to Freedom (account referencing Asbury Parker’s 1857 escape from Greenup County in broadcloth).
Nina M. Biggs and Mabel L. Mackoy, History of Greenup County, Kentucky (Evansville, 1951).
The Paper Trail of the Civil War in Kentucky 1861–1865, Kentucky National Guard, especially the “Civil War in Greenup County” entry.
“Kentucky’s Civil War: Greenup County’s Camp Swigert,” Kentucky Legislative Research Commission summary for marker 2247.
Civil War Governors of Kentucky Digital Documentary Edition, especially records connected to the 22nd Kentucky Infantry.
James M. Prichard, “Lingering War Zone: Post-Civil War Violence in Northeastern Kentucky,” The Filson History Quarterly.
Greenup County entries in The Kentucky Encyclopedia and the Notable Kentucky African Americans Database, including “Greenup County (KY) Enslaved, Free Blacks, and Free Mulattoes, 1850–1870.”