Appalachian History
On a late September night in 1861, lamplight spilled from the tall windows of a brick mansion just south of Grayson. Inside Landsdowne Hall, a circle of young men passed plates around Dr. Andrew Jackson Landsdowne’s table and spoke in low voices about rifles, road junctions, and the long ride ahead toward Confederate lines in eastern Kentucky. Outside, in the dark along the lane, the click of gun hammers told a different story. The Grayson Home Guard had quietly surrounded the house and were about to pull Carter County into a war that would not truly end for another two decades.
From that first standoff at Landsdowne Hall to the burning of Olive Hill and the later Underwood War, Carter County’s Civil War story is one of borderland tension, guerrilla tactics, and neighbors who never fully laid their weapons down.
A Young Mountain County on the Border
Carter County was barely twenty years old when the first shots of the Civil War sounded. Created in 1838 from parts of Greenup and Lawrence Counties, it took its name from state senator William Grayson Carter. The new county seat at Grayson sat where roads along the Little Sandy River crossed the path from the Ohio River interior, a geography that would make the county a corridor for both Union and Confederate forces.
Before the war, Carter County’s economy mixed small farms with iron furnaces, salt works, and timber. The countryside around Olive Hill and the Tygarts Creek valley connected inland communities to the Ohio River markets at Greenupsburg and Catlettsburg.
Like much of eastern Kentucky, Carter County leaned Union in its voting patterns, yet its elites were divided. The Landsdowne family, owners of the imposing brick mansion near Grayson, held enslaved people and identified with the South. Many smaller farmers and tradesmen, however, enlisted in Union regiments once the fighting started. Historian Gerald P. Dyson has argued that this mix produced a county that was strongly Unionist in the aggregate, yet laced with Confederate sympathies powerful enough to fuel local recruitment, secret meetings, and eventually guerrilla bands.
Those tensions first exploded at Landsdowne Hall.
Landsdowne Hall: Secessionists at the Doctor’s House
On the night of September 30, 1861, about twenty five secessionist recruits gathered at Landsdowne Hall, a half mile from Grayson. Newspaper accounts and later research agree that the men had come from the Greenupsburg area with a clear plan. They intended to seize weapons from the Grayson Home Guard, then ride south to join Confederate forces assembling under John C. Breckinridge in eastern Kentucky.
Their host, Dr. Andrew Jackson Landsdowne, was a Transylvania University trained physician and substantial slaveholder. The 1860 census shows him owning several thousand dollars in personal property, including eleven enslaved people living in two quarters near the house. His prominence, and his reputation as what one source called a “leading disunion spirit” in the Grayson area, made his home a logical rendezvous point for Confederate recruits.
Unionist neighbors, however, moved faster than the recruiters expected. Learning that armed secessionists were dining at the mansion, local officials called out the Home Guard. Around fifteen men under a Captain McGuire quietly took positions around the house while the guests ate. In a joint report later quoted in the Frankfort Daily Commonwealth, Col. Sebastian Eifort of the Grayson Home Guard and Captain W. C. Stewart of Lewis County described how one Confederate rushed from the doorway with a drawn revolver and shouted for his companions to fire. McGuire’s thirteen year old son pulled the trigger first, killing the man and breaking the standoff. The remaining recruits surrendered after a brief exchange of shots.
The skirmish produced little bloodshed beyond that single fatality, yet it resonated far beyond the Little Sandy valley. Dyson notes that the New York Times, the Frankfort Daily Commonwealth, the Daily Louisville Democrat, the Cincinnati Daily Press, and the Ironton Register all carried reports about the “arrest of secessionists at the residence of Dr. Landsdowne” in Carter County.
For readers along the Ohio River, the story was a shock. It suggested that Breckinridge’s forces might attempt a thrust into northeastern Kentucky, using local sympathizers and back roads through counties that many had assumed were safely Union.
In the aftermath, Dr. Landsdowne left the county for much of the war. He leased his salt furnace and store to a Unionist entrepreneur and moved his family closer to the Ohio River. The brick mansion survived the conflict, though by then its name had become shorthand for the moment Carter County first stared civil war in the face.
Morgan Rides into Carter County: The Burning of Olive Hill
A year later, Carter County faced a far larger crisis. In late summer 1862, Confederate brigadier general John Hunt Morgan led a swift cavalry column through eastern Kentucky, harassing Union general George W. Morgan’s retreat from Cumberland Gap toward the Ohio River. In his official report, later printed in the War of the Rebellion records, George Morgan complained that Confederate raiders “occupied Grayson, the county seat of Carter County, with a few hundred” troopers while shadowing his route north.
After briefly occupying Grayson, Morgan’s men pivoted west toward Olive Hill and the Tygarts Creek valley. Local tradition has long remembered this simply as “Morgan’s raid,” but both contemporary documents and modern scholarship suggest that it was closer to a running battle. Dyson and the Carter County Times estimate that roughly one thousand Confederate cavalry and allied guerrillas moved through the county, with four hundred or more Carter County Home Guards and militia turning out to oppose them.
As the raiders marched, they targeted Unionist households with particular fury. Among the most prominent victims was state senator William Grier, a pro Union politician whose home and store near Olive Hill were looted and burned.
The best contemporary glimpse of the crisis comes from a letter written on October 6, 1862, by Col. Sebastian Eifort from Boone Furnace to Kentucky’s Union governor, James F. Robinson. In the letter, preserved today in the Civil War Governors of Kentucky project, Eifort reported that the Confederate force was encamped at Olive Hill with “11 to 1200” men and two pieces of artillery, and that they had taken control of the state road between Catlettsburg and Owingsville.
Eifort believed he could raise “four or five hundred” Home Guards if the state would arm and support them. That estimate aligns with a separate citizen petition describing heavy skirmishing along Tygarts Creek and Flat Fork on October 1, as Morgan’s troopers attempted to withdraw westward while under fire from hills on both sides of the road. Dyson argues that the scale of the fighting justifies calling the engagement the Battle of Olive Hill or the Battle of Tygarts Creek, rather than simply a raid.
Newspapers agreed that Morgan paid dearly for his destruction. An October 13, 1862 report in the Louisville Daily Journal, quoted by Dyson and the Carter County Times, credited Carter County Home Guards with killing about thirty of Morgan’s men in the pursuit from Olive Hill, with another forty or fifty shot down by George Underwood and his irregulars near the Rowan County line.
Those numbers are difficult to verify precisely, yet the combined testimony of Louisville papers, Eifort’s letter, and local petitions all point to intense combat and significant casualties on the Confederate side. At the same time, Morgan’s men burned roughly forty five homes and farm buildings and turned families into refugees along their route through western Carter County.
For residents of the Tygarts valley, the war now meant more than distant headlines. It had put torches to their barns, their haystacks, and their front porches.
Carter Countians in Blue, Gray, and Guerrilla Bands
Although Carter County never saw a large set piece battle like Perryville, its people fought in major campaigns from Mississippi to the Shenandoah. Recruitment in northeastern Kentucky fed several Union regiments, most notably the 14th and 22nd Kentucky Infantry. Dyson and county historians identify the 22nd as especially tied to Carter County, since companies were raised and mustered in nearby towns such as Grayson and Louisa.
Pension and service records give that connection a human face. A Carter County pension file for Sherwood Tackett, transcribed by the KyGenWeb project, records that he enlisted at Grayson in 1861 as a musician in Company D, 22nd Kentucky Infantry, before disability forced his discharge.
The Civil War Governors of Kentucky prosopography includes an entry for Stephen Nethercutt, a Virginia born farmhand living in Carter County by 1850. Nethercutt served in the 22nd Kentucky as a second and first lieutenant, then as a captain, between January 1862 and May 1864, a trajectory that illustrates how men from the Little Sandy valley could rise through the ranks in volunteer regiments.
Once in federal service, Carter County’s Union soldiers saw hard campaigning far from home. Regimental histories and later summaries describe the 22nd Kentucky fighting at Chickasaw Bayou near Vicksburg, at Arkansas Post, through the Vicksburg campaign itself, and in the Red River and Louisiana operations. One Kentucky Historical Society feature on the regiment’s battle flag notes that after the charge at Chickasaw Bayou the colors were described as “torn” and “dripping with blood,” and that Colonel George W. Monroe proudly returned the flag to Frankfort in 1864.
Carter County also sent men into Confederate service. The most detailed window into that world comes from the contested congressional election case of McKee versus Young. In 1867, Republican Samuel McKee challenged Democrat John D. Young’s victory in Kentucky’s Ninth Congressional District by arguing that former Confederates had illegally voted. Investigators collected depositions from witnesses in each county, including Carter.
Those depositions, printed in a federal House document and later transcribed for Marlitta H. Perkins’s “Carter County Confederate Soldiers” blog post, list roughly 120 Carter Countians who had served in the “rebel army.” In testimony from men such as John P. Stephens of Grayson, William Bowling, and Moses Nethercutt, neighbors named former Confederate soldiers, identified their regiments when known, and often noted whether men had later enlisted in the Union militia.
The picture that emerges is complicated. Some Carter Countians rode with regular Confederate units early in the war, then slipped back across the mountains and joined guerrilla bands. Others deserted the Confederacy and enlisted in Home Guard or state militia units, blurring the line between ex Confederate and loyal militiaman.
One of the most infamous Confederate leaning guerrilla outfits associated with Carter County was led by William Jason Fields of the Olive Hill area, grandfather of future governor William J. Fields. Dyson describes Fields’s men, sometimes remembered as Fields’s Partisan Rangers, as a loose band that harried Union forces and aided Confederate operations in eastern Kentucky until captured near Cumberland Gap in 1864.
Volunteer infantry, Confederate cavalry, and irregular rangers together ensured that Carter County’s involvement in the war extended far beyond its boundaries, even when the fighting there took the form of raids and ambushes rather than traditional battles.
Corridors and Crossroads: Other Raids and Skirmishes
Morgan’s 1862 passage was not the only time Carter County’s roads and rail lines drew fire. Throughout the conflict, its valleys served as corridors for troops, refugees, and raiders.
The route of George W. Morgan’s retreat from Cumberland Gap to the Ohio River, for example, ran through West Liberty and Grayson to Greenupsburg. A regimental history of the First Tennessee Cavalry describes how Confederate forces harassed the column along this route, highlighting the importance of the Little Sandy and Tygarts Creek valleys in connecting central Appalachia to the Ohio.
Later in the war, the iron industry around the Carter Greenup line became a target. In June 1864, raiders struck near Star Furnace and Williams Creek, stealing horses and supplies. Local diarist J. Bertrand Norris, whose entries were later quoted by historian George Wolfford and expanded upon by James M. Prichard in “War Comes to Williams Creek,” recorded the growing sense that the war had finally come home in the form of burning barns, stolen livestock, and sudden violence on familiar roads.
Eastern Kentucky and the Civil War blog posts also point to a smaller raid on Olive Hill in July 1863, connected to Sid Cook’s guerrillas. These raids, combined with the constant presence of armed bands on both sides, made Carter County feel less like a quiet rear area and more like a contested border zone even in years when large armies were fighting elsewhere.
The Underwoods and a War that Would Not End
Perhaps nothing illustrates the lingering impact of the war in Carter County more clearly than the story of the Underwood family.
George W. Underwood lived along Tygarts Creek when Morgan’s troopers swept through western Carter County in 1862. According to Pritchard’s study “A Lingering War Zone,” Morgan’s men burned Underwood’s house during the Olive Hill fighting, an experience that shaped the family’s fierce Unionism. George’s son, Alfred, soon helped organize a band of Tygart Home Guards. These irregulars patrolled a wide swath of territory extending to Maysville, Portsmouth, and Ironton, protecting Union communities from Confederate raiders and allied bandits.
The Underwoods never became fully regular soldiers. They did not muster formally into U.S. service or draw army pay. They were, in Pritchard’s words, heavily armed men who combined loyalty to the Union with a readiness to settle scores by force.
After Appomattox, they kept their weapons. Feuds over politics, land, and old wartime grudges escalated into what became known as the Underwood War in the 1870s. The conflict pitted the Underwoods and their allies against the Holbrook and Stamper families and their supporters.
Pritchard and journalist Jeremy D. Wells recount how a string of killings, starting with disputes over tenants and stolen horses, eventually drew state attention. A notorious “whiskey incident” in which Jesse Underwood killed a bystander during an argument over a Jefferson Davis brand whiskey added to their outlaw reputation. Later, killings and ambushes on both sides culminated in Jesse Underwood’s death and then the cold blooded murder of the elderly, disabled George Underwood by masked men who entered his home under cover of night.
The violence became so severe that Kentucky’s governor ordered state troops into Carter County in 1879. These Regulators, commanded by Captain J. N. Stewart, built a fortified house near Grayson and attempted to impose order on a countryside still scarred by wartime loyalties. Pritchard argues that the Underwood War was not a random feud but an outgrowth of Civil War era militia networks and guerrilla practices that survived into Reconstruction.
In other words, the same currents that had produced Home Guards at Landsdowne Hall and irregular fighters at Olive Hill were still shaping life along Tygarts Creek almost fifteen years after Appomattox.
Why Carter County’s Civil War Story Matters
Carter County’s Civil War history can be easy to overlook. No national battlefield park marks its hills. Its major actions were small in scale compared to Chickamauga or Antietam. Yet that is precisely what makes the county’s story valuable.
Here, in a landscape of iron furnaces, small farms, and creek bottom roads, we can see how the Civil War functioned in a border county where most people supported the Union, yet neighbors and kin crossed over to the Confederacy. We can see how the war’s blurred lines between soldier, guerrilla, and outlaw persisted long after formal armies stacked their arms.
The Landsdowne Hall skirmish reminds us that news of a single failed recruiting party could travel from Grayson to New York in a matter of days, convincing readers that Confederate troops might soon threaten the Ohio. Olive Hill and the Tygarts Creek fighting show how a raid on paper could feel like a full scale battle to families whose homes and barns went up in flames. The depositions from McKee versus Young prove that questions about who had worn gray or blue did not end in 1865, but shaped voting rights and political legitimacy for years afterward.
Finally, the Underwood War demonstrates that Reconstruction in the Kentucky hills could be just as violent as the better known feuds of the Tug or Big Sandy valleys. Armed men who had once been Home Guards or guerrillas did not simply fold back into peaceful farm life. They brought wartime habits, grievances, and firepower into an era of railroads and industrial development.
Today, projects like the Civil War Governors of Kentucky, the Eastern Kentucky and the Civil War blog, and the Carter County Historical Society’s programs are making that history accessible again by digitizing letters, pension files, and old newspapers and by walking the ground where skirmishes once took place.
For descendants tracing a name in a pension file, for Olive Hill residents who still tell stories about Morgan’s raid, or for anyone trying to understand how national conflicts seep into local lives, Carter County offers a powerful case study in how a war can linger long after the shooting stops.
Sources & Further Reading
Official Records of the War of the Rebellion, Series I, Vol. 16, Part 2, reports of Gen. George W. Morgan and others on the Cumberland Gap retreat and operations near Grayson.
Sebastian Eifort to Gov. James F. Robinson, Boone Furnace, Kentucky, October 6, 1862, Civil War Governors of Kentucky, accession KYR 0001 029 0179, describing Confederate forces at Olive Hill and Home Guard strength. FromThePage
Petition and reports concerning the Battle of Olive Hill and Tygarts Creek, Civil War Governors of Kentucky collection, citizen descriptions of the 1862 engagement. Academia+1
Frankfort Daily Commonwealth, October 4, 1861; Daily Louisville Democrat, October 6, 1861; Cincinnati Daily Press and Ironton Register, early October 1861, contemporary accounts of the Landsdowne Hall affair. Eaky Civil War+1
New York Times, October 8, 1861, coverage of the arrest of secessionists at the residence of Dr. Landsdowne in Carter County, Kentucky. Academia+1
Louisville Daily Journal, October 13, 1862, report on casualties inflicted on Morgan’s men by the Carter County Home Guard and George Underwood’s command. Carter County Times+1
House Miscellaneous Document No. 13, 40th Congress, 2nd Session (McKee vs. Young contested election, 1868), depositions naming Carter County Confederate soldiers; see also Marlitta H. Perkins, “Carter County Confederate Soldiers,” Eastern Kentucky and the Civil War blog. Eaky Civil War
Sherwood Tackett pension application, KyGenWeb transcription, documenting enlistment at Grayson in Company D, 22nd Kentucky Infantry (U.S.). Kygen Web
Civil War Governors of Kentucky prosopography entry for Stephen Nethercutt, Carter County farmhand and officer in the 22nd Kentucky Infantry. Civil War Governors of Virginia
Gerald P. Dyson, “Carter County, Kentucky in the Civil War,” public lecture and paper presented for the Carter County Historical Society, 2022, synthesizing recruitment, Landsdowne Hall, Morgan’s raid, and guerrilla activity. Academia+1
Marlitta H. Perkins, “Skirmish at Landsdowne Hall,” Eastern Kentucky and the Civil War (2011), detailed narrative of the 1861 fight with extensive quotations from contemporary newspapers and later reminiscences. Eaky Civil War
Jeremy D. Wells, “Understanding the Battle of Olive Hill,” Carter County Times, February 2, 2022, summary of Dyson’s research on Morgan’s raid and the Home Guard response. Carter County Times
Jeremy D. Wells, “Looking at the Underwood War,” Carter County Times, August 31, 2022, report on James M. Pritchard’s work and the Underwood family’s role in local Civil War era violence. Carter County Times
James M. Prichard, “A Lingering War Zone: Post Civil War Violence in Northeastern Kentucky,” Register of the Kentucky Historical Society, 2014, analysis of the Underwood War, Regulators, and the continuity of wartime violence. The Filson Historical Society
Frank Merritt and the Carter County Bicentennial Committee, Carter County History, 1838 1976; L. B. Criswell, Carter County; and George Wolfford, Carter County: A Pictorial History, for broader county background and Civil War era anecdotes. RootsWeb+1
Carter County Fiscal Court, “About Carter County” web page, for basic county formation and naming details. cartercountyky.com