Appalachian History
Fleming County does not appear in the standard lists of great Civil War battlefields. No Perryville, no Mill Springs, no Cumberland Gap. Yet the war brushed this corner of northeastern Kentucky again and again, in fleeting cavalry clashes, telegraph raids, guerrilla robberies, and tense exchanges between county officials and Frankfort.
Piecing those fragments together reveals a community that lived inside a low-level war. The official markers and encyclopedias say only that “small skirmishes” touched the county and that John Hunt Morgan’s raiders passed through. The paper trail is richer than that. Diaries, federal unit histories, guerrilla timelines, and petitions to the governor show Flemingsburg and its outlying villages acting as crossroads, outpost, and occasional target in a conflict that never hardened into a full scale battle yet never really let go.
Fleming County on the Eve of War
By 1860 Fleming County was an old Kentucky county, formed in 1798 with Flemingsburg as its seat. Small farms, market towns, and the Maysville road tied it to the Ohio River and the Bluegrass. Slavery existed but on a smaller scale than in the central Bluegrass counties, a pattern that would help make northeastern Kentucky a contested but mostly Union-leaning region once the shooting began.
That background matters because it helps explain why the war in Fleming County looked more like raids and reprisals than like set-piece infantry battles. This was a county on a line: not quite the slave-rich heart of Kentucky, not quite free-soil Ohio, but a place where telegraph lines, stage routes, and later railroads linked competing loyalties.
Hillsborough and Elizaville: Small Battles in a Borderland
The first clear sign that the national crisis had reached Fleming County appears in the federal battle summaries compiled by Frederick Dyer, now accessible through the National Park Service. Under the year 1861 the Kentucky section lists an “Oct. 8 Skirmish, Hillsborough” and adds that the troops involved were the “Flemingsburg Home Guard,” with Union losses given as three killed and two wounded. The entry is brief, but it anchors local tradition in the official record. Somewhere near Hillsboro, only a few months after Bull Run, local Unionist militia found themselves in a real fight, one bloody enough to leave five casualties out of a very small force.
Later statewide summaries of the war in Kentucky, compiled by the Kentucky Historical Society and the National Guard in The Paper Trail of the Civil War in Kentucky 1861–1865, compress this experience into a single sentence: “The Civil War brought small skirmishes to Fleming County, including one in 1862 as Gen. John Hunt Morgan’s raiders retreated from their attack on central Kentucky towns.” That line grew out of highway markers and county histories and represents what the state’s historians were willing to certify in metal.
Local memory fills in a few more details. The KyGenWeb “History of Elizaville,” drawing on earlier recollections, notes that there was “a clash of arms near the village of Elizaville” during the war and ties it to Confederate incursions in the area. A later feature story on Fleming County heritage tourism in the Maysville newspaper described this Elizaville encounter as “the only Civil War battle fought in Fleming County,” placing it in 1862 and associating it with a Confederate Captain Jackson, while frankly admitting that “few details are known.”
Put together with the Paper Trail summary, these sources suggest a small engagement near Elizaville during Morgan’s 1862 retreat from central Kentucky. In the summer and fall of that year Morgan’s cavalry swept through Kentucky and into the Licking River country, sparring with home guard units and tearing up communications. A telegraph history by William R. Plum later listed Flemingsburg and nearby Maysville among the communities where Morgan’s men severed lines and disrupted messages, underscoring how vulnerable northeastern Kentucky was to fast-moving cavalry.
The Elizaville skirmish never received the official battle name that places like Augusta or Cynthiana earned. Yet for local families, a brief exchange of shots in a pasture or along a pike was memorable enough to survive in oral history and county sketches more than a century later.
Garrison on the Ridge: Flemingsburg as a Union Base
By 1863 Fleming County had become part of the larger “District of Eastern Kentucky,” an administrative zone that federal commanders treated as a trouble spot. Confederate recruiters, small cavalry bands, and outright guerrilla groups moved through the hills, while Union officers struggled to protect roads and loyal citizens without alienating the very communities they meant to defend.
One key piece of evidence for Fleming County’s military role comes from the National Park Service’s battle unit history for the 5th Independent Battalion, Ohio Cavalry. Organized for six months’ service in 1863, the battalion “moved into [the] District of Eastern Kentucky, Headquarters at Flemingsburg,” where it spent the rest of its term “engaged in scouting and raiding guerrillas in that District till February, 1864.”
That one sentence confirms that Flemingsburg served as a Union cavalry post through the fall and winter of 1863–64. Federal troopers rode in and out on narrow roads, looking for guerrilla camps, escorting supply trains, and responding to reports of raiders in neighboring counties. The battalion history notes skirmishes in Morgan County and at Liberty, but its Flemingsburg headquarters meant that the town itself felt the rhythms of a war against elusive enemies, not regular Confederate regiments.
Other units, such as the 10th Kentucky Cavalry (Union), also used Flemingsburg as a jumping-off point. A detailed modern reconstruction of Col. William Everett’s June 1863 raid through eastern Kentucky notes that by mid June the 10th Kentucky Cavalry had reached Flemingsburg and pushed on in pursuit, trying to close the distance between Federal forces and Everett’s small Confederate command as they moved east through Hillsboro and beyond.
Here the official records and later research blogs converge. They show Fleming County not as a bystander but as part of the logistical backbone for Union efforts to police a broad swath of northeastern Kentucky.
Cook’s Devils and the Sack of Flemingsburg
If the Elizaville skirmish represents Fleming County’s brush with conventional Confederate cavalry, the most dramatic wartime incident within the county seat itself came not from a regular regiment but from a guerrilla band.
In early September 1863 a group of irregular Confederate fighters commanded by Sidney, or “Sid,” Cook swept into Flemingsburg. James M. A. Pritchard, in a study of post-war violence in northeastern Kentucky, notes that in the autumn of 1863 Cook’s band, often called “Cook’s Devils,” took part in the “sack of Flemingsburg” and later robbed a bank at Ashland.
A heavily footnoted Eastern Kentucky Civil War research blog reconstructs Cook’s movements day by day from contemporary newspapers and Official Records reports. Its entry for 2 September 1863 simply states: “Cook and his men robbed the bank and citizens in Flemingsburg, KY.” That stark sentence matches what Kentuckians in Lexington were hearing.
The best near-contemporary account comes from a young Unionist diarist, Frances Dallam Peter of Lexington. Writing on Friday, 4 September 1863, she recorded that on the previous Wednesday “a party of some seventy or eighty guerrillas entered Flemingsburg, Ky and robbed the bank,” adding that they also stripped local citizens of money and weapons. Peter never saw Flemingsburg herself; she was repeating news that circulated quickly along the turnpikes and telegraph lines. Still, as a dated primary source her diary helps pin the raid to the first days of September and gives a sense of its scale.
Between Peter’s diary, the guerrilla timeline, and Pritchard’s later analysis, a plausible picture emerges. Cook’s men, perhaps seventy strong, rode into Flemingsburg in broad daylight, seized roughly five hundred dollars from the local bank, and plundered private pockets besides. They then escaped before any substantial Union force could respond, later pulling a similar robbery at Ashland.
For townspeople, the line between “regular” war and outlawry must have blurred. The raiders claimed Confederate allegiance and operated in a state where legitimate Confederate cavalry had passed only the previous year. Yet their actions looked more like banditry than battlefield glory. In that sense the sack of Flemingsburg fits an eastern Kentucky pattern, where guerrillas and counter-guerrillas turned the war into something that felt personal and lawless long after big armies had marched on.
A County on Morgan’s Line of March
Even when no shots were fired inside the county, Fleming County lay in the path of some of the war’s most famous cavalry campaigns. On his final Kentucky raid in June 1864, John Hunt Morgan led several thousand men into the Bluegrass, capturing Mt. Sterling, briefly seizing Lexington, and fighting costly engagements at Cynthiana before being forced to retreat toward the Virginia border.
The same Paper Trail compilation that summarizes the Elizaville skirmish also notes that during this last raid Morgan’s command “retreated west of Flemingsburg, reaching Virginia 20 June 1864.” A Kentucky Historical Society marker dedicated to that raid further specifies that Morgan entered the region near Mt. Sterling, moved across central Kentucky, then fell back through or near Flemingsburg on his way east, camping in the area in mid June before quitting the state for good.
For Fleming County residents, the 1864 raid would have brought rumors of battles at Mt. Sterling and Cynthiana, a surge of wounded men moving across the countryside, and reports of telegraph lines down yet again. Even if Morgan’s column skirted the county seat rather than occupying it, the nearness of thousands of cavalrymen must have been a sobering reminder that the war could still arrive in force.
James J. Andrews and the Flemingsburg Connection
Oddly enough, Fleming County’s best-known Civil War figure was not a native son but a wandering civilian spy whose most famous exploit unfolded hundreds of miles away.
A Kentucky Historical Society highway marker, summarized in the Fleming County section of The Paper Trail, notes that “James J. Andrews lived in Flemingsburg in 1859–62.” A house-painter by trade and sometime contraband runner for the Union, Andrews used Flemingsburg as his base while slipping across lines in the early years of the war. In April 1862 he led twenty-two Union volunteers south into Georgia in an attempt to steal a locomotive named The General and sever the Western & Atlantic Railroad between Atlanta and Chattanooga. Captured when the raid failed, he was hanged as a spy at Atlanta in June 1862.
Andrews’s Flemingsburg connection resurfaces a year later in a letter preserved in the War of the Rebellion: Official Records and reprinted in a nineteenth-century pamphlet. Dated “FLEMINGSBURG, KY., March 31, 1863” and addressed to Judge Advocate General Joseph Holt at Washington, the letter was written by a soldier of the 4th Ohio Cavalry who had known Andrews. He wrote to correct newspaper stories about the raid and to defend Andrews’s character and loyalty.
Even if most Fleming County residents never met Andrews personally, the presence of a Great Locomotive Chase witness inside the county underscores how tightly this “quiet” place was woven into the broader tapestry of the war. Flemingsburg served not only as a cavalry post and guerrilla target but also as a node in the flow of stories and memories that would later feed national legend.
Everyday Voices from a Small War
Beyond battles, skirmishes, and raids, the war’s impact on Fleming County shows up in the petitions, letters, and legal documents preserved in the Civil War Governors of Kentucky Digital Documentary Edition. A search of that archive turns up multiple documents created at “Flemingsburg, Fleming County, Kentucky” and “Elizaville, Fleming County, Kentucky” between 1861 and 1865, including correspondence and petitions to Governor Beriah Magoffin and his Unionist successors.
One example is an April 25, 1861 letter from Joseph M. Alexander of Flemingsburg to Governor Magoffin, classified as “correspondence” in the CWGK index. Others involve requests for pardons, complaints about local law enforcement, and reports of disturbances. While each document turns on its own facts, collectively they remind us that county judges, merchants, and ordinary citizens spent the war negotiating questions of loyalty, security, and justice with the state government.
Newspapers add another layer, even when they date from just after the war. Titles like the Flemingsburg Democrat, preserved in Morehead State University’s digital archives, and listings on OldNews.com for prewar and postwar Fleming County papers show how local editors framed the conflict in retrospect and how veterans’ obituaries and anniversary pieces kept alive memories of skirmishes like Elizaville and Hillsboro.
Aftermath: A Lingering War Zone
For Fleming County, the formal end of the Civil War did not mean an abrupt return to peace. Pritchard’s “A Lingering War Zone: Post–Civil War Violence in Northeastern Kentucky” traces how wartime guerrillas, hard feelings, and unsettled scores bled into Reconstruction-era feuds and crimes in counties like Bath, Rowan, and Fleming. Judges and governors wrestled with petitions from men accused of murder and banditry whose defenders cited their Confederate service or wartime grievances.
Other research on eastern Kentucky cavalry operations records that even late in the war Federal soldiers were still being shot from ambush near Flemingsburg, a reminder that the home guard and small Union detachments remained targets long after the major campaigns had rolled west and south.
Seen from this angle, the sack of Flemingsburg in 1863 and the skirmish at Hillsborough in 1861 are not isolated curiosities but episodes in a long arc of violence and contested authority that stretched well into the 1870s.
Sources & Further Reading
The Paper Trail of the Civil War in Kentucky 1861–1865 (Kentucky National Guard / Kentucky Historical Society), Fleming County and Morgan raid entries. KY National Guard History+1
Wade Cooper, Early Fleming County Kentucky Pioneers (Ashland, 1974; reprint 2019), cited in the Paper Trail as a key source for local Civil War incidents. KY National Guard History
“History of Elizaville,” KyGenWeb Fleming County pages, and the locally published “Historical Tales of Elizaville,” both preserving memory of a Civil War “clash of arms” near the village. Kygenweb+1
“Fleming County: Riding the Rails of History,” Maysville online feature (2012), describing the Elizaville fight as the county’s lone “battle” and attributing it to a Captain Jackson in 1862. Maysville Online
National Park Service, “Kentucky Battles” (from Dyer’s Compendium), entry for the October 8, 1861 skirmish at Hillsborough involving the Flemingsburg Home Guard. National Park Service
National Park Service, “Battle Unit Details,” 5th Independent Battalion, Ohio Cavalry (6 months, 1863–64), documenting Flemingsburg as headquarters for anti-guerrilla operations. National Park Service
Eastern Kentucky Civil War blog, “Cook’s Guerrillas” timeline, with contemporary documentation for the September 2, 1863 robbery of the bank and citizens in Flemingsburg. eakycivilwar.blogspot.com+1
Frances Dallam Peter, A Union Woman in Civil War Kentucky: The Diary of Frances Peter, edited edition whose September 4, 1863 entry reports that guerrillas entered Flemingsburg and robbed the bank, based on news from northeastern Kentucky. Ethernet University
James M. A. Pritchard, “A Lingering War Zone: Post–Civil War Violence in Northeastern Kentucky,” Register of the Kentucky Historical Society, analyzing Cook’s Devils, the sack of Flemingsburg, and the persistence of violence into the Reconstruction era. The Filson Historical Society
Eastern Kentucky Civil War blog, “Everett’s June 1863 Raid – A Detailed Account,” noting the 10th Kentucky Cavalry’s presence at Flemingsburg while pursuing Confederate raiders through Hillsboro and beyond. eakycivilwar.blogspot.com
Civil War Governors of Kentucky Digital Documentary Edition, various documents created at Flemingsburg and Elizaville between 1861 and 1865, including Joseph M. Alexander’s April 25, 1861 letter to Governor Beriah Magoffin. test.discovery.civilwargovernors.org+1
“Two Letters, one of which was written by J. J. Andrews” (transcript from the Official Records), especially the March 31, 1863 letter from a 4th Ohio Cavalry soldier at Flemingsburg to Judge Advocate General Joseph Holt concerning Andrews and the locomotive raid. Pddoc
Morehead State University, “Flemingsburg Democrat Archive,” and OldNews.com listings for Fleming County newspapers before and after the war, documenting how local editors remembered these events. facebook.com+2HMDB+2