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 secession, enslaved men near the Little Sandy tried to seize a skiff and row themselves toward freedom in Ohio, only to end their lives on the gallows at Greenup. 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.
“Affray and Murder” on the Little Sandy
Two decades before Fort Sumter, the county had already seen a violent clash over slavery. On a Friday afternoon in the 1840s, a group of enslaved men on the Little Sandy River, just outside Greenup, seized a small boat and tried to row toward the free soil of Ohio. According to an antislavery newspaper account later reprinted under the headline “Affray and Murder,” the enslavers pursued them, guns in hand. In the confrontation that followed, one white slaveholder died and the enslaved men were captured. A Greenup jury condemned several of them to hang.
Historian Andrew Lee Feight ties this “Greenup Slave Revolt” to the wider atmosphere stirred by David Walker’s 1829 Appeal to the Colored Citizens of the World, a pamphlet that argued for Black resistance to slavery and circulated along the Ohio River valley despite efforts to suppress it. The revolt unfolded only a short walk from the courthouse hill where later Civil War markers would be planted.
Greenup also appears in Underground Railroad lore. In the late nineteenth century history 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 uprisings, 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
On 24 October 1861, state authorities established Camp Swigert on bottomland just east of Greenupsburg near Fulton Landing. The site offered what the army needed: flat ground, access to the turnpike, and the deep, steady water of the Ohio for steamboats bringing supplies and recruits.
From November into December, men from Greenup, Boyd, Carter, Lewis, Franklin County, and even Louisville poured into the camp. There the 22nd Kentucky Infantry took shape. The Civil War Governors of Kentucky project and regimental references agree that the unit was organized at Camp Swigert late in 1861 and mustered into United States service in early January 1862 with Daniel W. Lindsey and later George W. Monroe as colonels.
A Kentucky Legislative Research Commission summary of the Camp Swigert marker notes that recruits from Camp Swigert soon found themselves on the slopes above Middle Creek near Prestonsburg. In January 1862, part of the 22nd joined other Union units under Colonel James A. Garfield in an attack that helped secure eastern Kentucky. Garfield later praised their bayonet charge as decisive in turning the tide of the fight.
After Middle Creek, 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 to fight in the Vicksburg campaign. At Chickasaw Bayou they suffered heavy losses, their battle flag left “torn” and stained with blood, according to their division commander. One soldier, John T. Harrington, later summed up his experience with the stark line, “I have seen war in all its horrors.”
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 under John Hunt Morgan. Many were already weakened by short rations. They drove cattle ahead of the army, foraged for corn, and helped refugees fleeing East Tennessee cross the same roads.
The Kentucky Historical Society highway marker titled A Masterful Retreat stands today on the courthouse lawn in Greenup. Drawing on official reports and The Kentucky Encyclopedia, it records that approximately eight thousand of George Morgan’s soldiers reached Greenup on 3 October 1862 on their way to Camp Dennison near Cincinnati after the long retreat from Cumberland Gap.
For local residents, the arrival must have been overwhelming. Contemporary accounts describe Union columns filling the streets of small towns at the end of long marches. 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.
The Ohio River, which enslaved men had once tried to cross in a stolen skiff, now carried soldiers instead. Steamboats ferried Morgan’s command away from Greenup, but the memory of their passage lingered in local lore and on the bronze face of marker 520.
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 welcomed Morgan’s retreat in 1862 later scouted back roads and river crossings in search of guerrillas. The Tygart and Little Sandy valleys became corridors of patrols and ambushes. 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 “our mountains here, and we, the 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.
The violence spilled across county lines, with killings in Carter, Elliott, and Lewis counties reported in papers from Louisville to New York. It took nearly a decade, along with a combination of state pardons and troop deployments, to quiet the worst of the feuding. Prichard and other scholars point out that many of the men involved first gained arms, training, and enemies in the Civil War years.
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. Scioto Historical’s work on the Greenup Slave Revolt, together with the Portsmouth Western Times report “Affray and Murder,” offers rare glimpses of enslaved men from the area 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, among them Dr. William S. Kouns, who briefly joined the 5th Kentucky Mounted Infantry before returning home under General William Nelson’s amnesty. That imbalance helps explain why local memory and modern markers emphasize Union service, from Morgan’s retreat to the 22nd’s bloody flag at Chickasaw Bayou.
At the same time, underground flight and local revolt remind us that Black residents had their own ways of fighting for freedom, ones not captured in blue or gray on a roster.
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 two markers in Greenup that frame the story: marker 2247 for Camp Swigert and marker 520, A Masterful Retreat, for Morgan’s march from Cumberland Gap.
The Civil War Governors of Kentucky Digital Documentary Edition lets researchers filter petitions, letters, and official documents by county, turning up everything from local boundary disputes on the Little Sandy to correspondence about Greenup soldiers. 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.
Scioto Historical’s feature on the Greenup Slave Revolt and the Notable Kentucky African Americans Database widen the lens beyond battles and uniforms, connecting the county to broader stories of Black resistance and the Underground Railroad. Prichard’s “Lingering War Zone,” published in The Filson History Quarterly, uses court files and newspaper coverage to show how Civil War guerrilla habits fueled later feuds along the Carter–Greenup line.
Old maps from the mid-nineteenth century, now digitized by projects like House Divided and commercial map libraries, help readers place all this in space: the courthouse square in Greenupsburg, Oldtown on the Little Sandy, the roads that led south toward the Gap.
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. Enslaved people near the Little Sandy risked everything to reach the Ohio. 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.
For families whose ancestors lived along the Ohio in northeastern Kentucky and southern Ohio, these stories explain why particular surnames appear in muster rolls, court records, and cemetery stones. For the wider public, Greenup’s experience reminds us that the Civil War’s front lines were not only at Shiloh or Gettysburg. They also ran through hillside farms, iron furnaces, ferry landings, and small courthouses that watched both enslaved people and soldiers come and go.
When you stand today on the courthouse lawn at Greenup and read the “Masterful Retreat” marker, it is worth remembering not only the nine thousand worn-out Union soldiers who passed through town in 1862, but also the enslaved men who seized a boat on the Little Sandy, 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).
Cincinnati-area and Ohio River newspapers, including the Ironton Register and Portsmouth Western Times, for coverage of the Greenup Slave Revolt and guerrilla raids. sciotohistorical.org+1
Civil War Governors of Kentucky Digital Documentary Edition, especially the entity record for the 22nd Kentucky Infantry and petitions relating to Greenup County. Civil War Governors
David Walker, Appeal to the Coloured Citizens of the World (1829), as contextualized by Scioto Historical’s discussion of the Greenup Slave Revolt. sciotohistorical.org+1
Andrew Lee Feight, “The Greenup Slave Revolt and David Walker’s Appeal to the Colored Citizens of the United States of America,” Scioto Historical. sciotohistorical.org+1
Nina M. Biggs and Mabel L. Mackoy, History of Greenup County, Kentucky (Evansville, 1951). NKAA+1
The Paper Trail of the Civil War in Kentucky 1861–1865, Kentucky National Guard, especially the “Civil War in Greenup County” entry. KY National Guard History+1
“Kentucky’s Civil War: Greenup County’s Camp Swigert,” Kentucky Historical Society / Kentucky Legislative Research Commission, marker 2247 summary. Kentucky Legislature+1
“Greenup County and the Civil War,” Eastern Kentucky and the Civil War blog, October 2022, and “Cook’s Guerrillas,” Eastern Kentucky and the Civil War, June 2010. Eaky Civil War+1
James M. Prichard, “Lingering War Zone: Post-Civil War Violence in Northeastern Kentucky,” The Filson History Quarterly. The Filson Historical Society+1
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.” NKAA+1
House Divided: The Civil War Research Engine at Dickinson College, “Greenup County, KY (Fanning’s, 1853),” for prewar geography and population data. House Divided