Appalachian History
On top of Big Hill, motorists on U.S. 421 cross three county lines in a matter of seconds. To the south lies Jackson County, carved from surrounding counties in 1858 and tied to older paths that long predate the Civil War. Historical markers at Gray Hawk recall the Warrior’s Path, an Indigenous route that followed War Fork Creek before climbing toward the Bluegrass.
Only a few years after Jackson County’s creation, those same routes carried blue and gray armies. Big Hill, the gap between the mountains and the Bluegrass, became the scene of a sharp cavalry fight on August 23, 1862. The action there opened the road to one of the most lopsided Confederate victories of the war at Richmond. It also brought the national conflict directly onto Jackson County’s ridges, creeks, and courthouse square.
Today the Cox Simpson House at the top of Big Hill serves as the county’s welcome center, but in 1862 it held wounded men from both sides. Outside stand markers and an interpretive panel about the “Battle of Big Hill,” and each summer a reenactment on nearby Jackson Energy Farm keeps the story alive.
Kirby Smith’s Invasion and the Road Over Big Hill
In August 1862 Confederate general Edmund Kirby Smith marched his Army of Kentucky north from Knoxville as part of the wider Heartland offensive. Smith hoped to knock Kentucky out of Union control, threaten Cincinnati and Louisville, and perhaps install a Confederate state government in Frankfort. Brigadier General Patrick Cleburne’s infantry division formed the backbone of the advance, with Colonel John S. Scott’s hard riding cavalry brigade screening ahead on the old state road from London over Big Hill toward Richmond.
Modern readers can trace this movement in several period sources. The official “Compendium of the War of the Rebellion,” drawing on the War Department’s records, lists an “Action, Big Hill” in the Kentucky section for August 23, 1862, involving the 7th Kentucky Cavalry and 3rd Tennessee Infantry on the Union side. A separate entry notes a skirmish “between Big Hill and Richmond” on August 29, followed by the Battle of Richmond or Mount Zion Church on August 30. These terse entries show how Federal clerks understood the fighting around Big Hill as part of a sequence that ran up the pike toward Richmond.
Kentucky’s own highway markers flesh out that story. Marker 1124, “Big Hill Skirmish,” stands just north of U.S. 421 near the junction of Madison, Jackson, and Rockcastle Counties. It summarizes the event in a few sentences: on August 23 some 650 cavalry of Kirby Smith’s invading Confederate army routed a small Federal force under Colonel Leonidas Metcalfe on the road toward Richmond, part of a campaign that briefly captured central Kentucky before ending with Confederate withdrawal after Perryville.
Scott and Metcalfe Clash on the Ridge
The official records for the campaign print after action reports by both sides, including Colonel Scott’s description of his cavalry’s advance and Union accounts of the scramble to delay the invasion. Jackson County tourism materials point modern readers to these reports by Scott, Wallace, and Kendrick in Series I, volume 16 of the War of the Rebellion, which collectively describe Confederate cavalry pushing north from London, seizing Big Hill, and driving Federal pickets before them.
On the Union side, Colonel Leonidas Metcalfe commanded elements of the 7th Kentucky Cavalry and emergency infantry support. According to later summaries based on those reports, Metcalfe’s mixed force took position near the crest of Big Hill, along the ridge line now crossed by U.S. 421. Scott’s brigade, which included the 1st Louisiana and 1st Georgia Cavalry, struck with superior numbers, driving the Federals back from the high ground and scattering their horsemen toward the Jackson County line.
The fight did not end at the summit. As Metcalfe’s men fell back, they formed a new line along the branch of Red Lick Creek near the road, using supply wagons as makeshift barricades. Contemporary interpretations of the ground, drawing on Hafendorfer’s and Lambert’s tactical studies, describe the 3rd Tennessee (Union) forming an L shaped defense along the creek and pike while Scott’s cavalry attacked across both the road and the stream. The Confederate charge broke the line, leaving Metcalfe’s command shattered and opening the highway toward Richmond.
Although the official numbering places the skirmish in Madison County, the ground of the fight straddles what are now county lines. The Cox Simpson House, built in 1839 and now interpreted as the Big Hill Welcome Center, sits on the Jackson County side of the ridge. Local tradition and tourism signage identify it as a field hospital where wounded from the Big Hill action received treatment, tying Jackson County directly to the day’s violence.
From Big Hill to Richmond
Big Hill was only the opening act. Six days later, on August 29, Scott’s cavalry again collided with Union forces while advancing from Big Hill toward Richmond. The National Park Service summary of the Battle of Richmond notes that seizing the road over Big Hill allowed Cleburne’s infantry and Scott’s horsemen to press north, where they skirmished with Union troopers before falling back to the ridge. Those contacts on the 29th appear in the federal battle lists as a “skirmish between Big Hill and Richmond,” a prelude to the full scale battle the next day.
On August 30, 1862, Kirby Smith’s army crushed Union general William “Bull” Nelson’s force south of Richmond, inflicting more than five thousand casualties in one of the war’s most lopsided Confederate victories. The road that crossed Jackson County’s corner at Big Hill had carried the Confederates into position for that triumph and then on to the short lived occupation of Lexington and Frankfort.
The same Kentucky marker that commemorates the Big Hill Skirmish also hints at the bigger picture, noting that although central Kentucky was captured in the wake of the 1862 campaign, Confederate plans to take Cincinnati and Louisville failed and the army ultimately retreated from the state after Perryville on October 8.
Jackson County on the Warrior’s Path
Civil War traffic over Big Hill and through McKee followed much older lines of travel. Historical Marker 697, “Warrior’s Path,” at Gray Hawk in Jackson County, points to an ancient Indigenous trail that once linked the Ohio Valley and the Cherokee country. The marker and supporting research note that this path ran along War Fork Creek in eastern Jackson County before turning north toward the Kentucky River.
By the mid nineteenth century, parts of this route overlapped or lay close to the old state road and later U.S. 421. The same geography that drew hunters, traders, and warriors now attracted Civil War commanders who needed a corridor between the Cumberland Gap region and the Bluegrass.
An official report from the winter 1862-1863 East Tennessee raid illustrates how thoroughly Union forces used these mountain roads. In Series I, volume 20 of the War of the Rebellion, Brigadier General S. P. Carter described assembling a cavalry column that included two battalions of the 2nd Michigan Cavalry and the 9th Pennsylvania Cavalry. After leaving the Goose Creek region in Clay County, he wrote that on the 22d he “came up with the two battalions Second Michigan and Ninth Pennsylvania at McKee, Jackson County, Kentucky,” where the combined force paused for a day while waiting on supply trains and pack saddles.
That single sentence places hundreds of Union horsemen and their support animals in and around McKee, turning the small mountain courthouse town into a logistical hub for a raid that pushed deep into East Tennessee. The same corridors that had carried Scott’s Confederates north in August now carried Federal columns south and east in winter.
Jackson Countians in Blue and Gray
County histories and modern genealogy guides make clear that Jackson County families had sons in both armies. The FamilySearch “Jackson County, Kentucky Genealogy” page aggregates links to Civil War service and pension records for both Union and Confederate soldiers. Behind those databases stand the state adjutant general’s reports for 1861-1866, which list volunteer regiments, companies, and individual soldiers, including many mountain regiments that drew heavily from Jackson and surrounding counties.
The Civil War Governors of Kentucky Digital Documentary Edition offers a closer look at individual Jackson Countians in uniform. Subject files there include men such as Thomas H. Wilson, a Jackson County merchant and soldier in the 7th Kentucky Volunteer Infantry, Henry J. Clark, a farmer who rose from private to captain in the same regiment, and Samuel “Hampton” Flanery, another Jackson County farmer who served as sergeant and lieutenant in the 7th Kentucky. Their petitions, letters, and legal records reveal wartime disputes over pay, promotions, and loyalty, placing Jackson County voices directly into the archival record.
On the ground, cemeteries preserve the memory of these veterans. A RootsWeb compilation titled “Civil War Soldiers Buried in the Tyner Cemetery” draws on headstones and the adjutant general’s volumes to identify Union soldiers interred at Tyner in northern Jackson County, including men of the 7th Kentucky Infantry and later home guard and mounted units. Find a Grave memorials extend that picture to smaller burial grounds, such as the Medlock Cemetery near Annville, where Andrew Jackson Isaacs is recorded as a member of Company D, 7th Kentucky Infantry who died in Jackson County on September 2, 1863.
These fragmentary records hint at the broader pattern. While Confederate cavalry rode the Big Hill road in 1862, Jackson County itself provided a steady stream of Union volunteers to mountain regiments that guarded the same region, escorted supply trains, and hunted guerrillas. At the same time, Confederate sympathizers and a smaller number of local men in gray added to the county’s internal tensions, a theme explored in recent scholarship on Unionism and guerrilla warfare in southeastern Kentucky.
A Jackson County Voice in The Liberator
One of the few wartime documents explicitly dated from Jackson County to reach a national audience appeared in William Lloyd Garrison’s abolitionist newspaper The Liberator. The issue of May 15, 1863 includes a letter with the dateline “Gray Hawk, Jackson County, Ky., April 13th, 1863.” Written from a post office on U.S. 421 between McKee and Big Hill, the letter gave Boston readers a glimpse of the war as seen from a small mountain community that had already watched armies march past its doors.
Even without parsing every line, the survival of that letter matters. It shows that Jackson County residents engaged national debates over emancipation, loyalty, and federal policy, and that correspondents in remote eastern Kentucky were willing to address those issues in a widely read antislavery paper. Alongside muster rolls and marker texts, it stands as another thread connecting Big Hill and Jackson County to the larger story of the Civil War.
Memory, Markers, and Reenactment
After the guns fell silent, the Big Hill corridor remained important. The old state road became U.S. 421, and Jackson County’s identity coalesced around its place between Cumberland Gap and the central Bluegrass. Twentieth century heritage programs layered new meanings onto the landscape.
Kentucky’s highway marker program placed multiple signs in and around Jackson County, including the Big Hill Skirmish marker at the crest of the hill and the Warrior’s Path marker at Gray Hawk. The Kentucky National Guard’s booklet “The Paper Trail of the Civil War in Kentucky 1861-1865” treats these markers as an official inventory of Civil War sites, listing Jackson County alongside its neighbors in discussions of campaigns, retreats, and courthouse fires.
At the top of Big Hill, Jackson County Tourism has transformed the Cox Simpson House into the Big Hill Welcome Center, complete with displays on the 1862 fighting, the hospital role of the house, and the later Battle of Richmond. Outside, an interpretive panel produced in cooperation with Friends of the Richmond Battlefield and other partners explains the course of the battle and situates Big Hill within the wider campaign.
The annual “Battle of Big Hill” reenactment, held on Jackson Energy Farm along Highway 290, brings these histories to life for visitors. Confederate and Union reenactors stage the clash between Scott’s cavalry and Metcalfe’s outnumbered Federals, while living history programs interpret camp life, medical care, and civilian experiences in the wartime county.
Conclusion
Big Hill’s Civil War story is a story of a crossroads. Before 1860, the ridge stood along a Native trail and frontier road that linked mountains and Bluegrass. In 1862 it became the gateway through which Confederate forces surged north, driving Union horsemen back toward Richmond and helping to set up one of the war’s most complete Confederate victories. In the years that followed, Union raids, cavalry columns, and supply trains also threaded through McKee and Gray Hawk, relying on Jackson County roads and farms to sustain operations.
For local families, the war did not appear only as columns on distant horizons. It meant sons in the 7th Kentucky Infantry, men buried at Tyner and Medlock, petitions to the governor over pay and promotions, and a rare letter from Gray Hawk printed in an abolitionist newspaper. The markers at Big Hill and along the Warrior’s Path, the Cox Simpson House hospital, and the modern reenactment together remind us that Jackson County, though small and remote, stood at the fault line between mountain and Bluegrass, between Union and Confederacy. Its Civil War history belongs not just to Madison County battlefields or distant archives, but to the hills and hollows that Appalachian travelers still cross today.
Sources & Further Reading
War of the Rebellion: Official Records of the Union and Confederate Armies, Series I, volume 16, part 1, Kentucky Campaign reports (including Scott’s cavalry and related operations around Big Hill and Richmond). Accessible via the Portal to Texas History and other digital collections.
War of the Rebellion: Official Records of the Union and Confederate Armies, Series I, volume 20, part 1, report of Brigadier General S. P. Carter describing concentration of 2nd Michigan and 9th Pennsylvania Cavalry at McKee, Jackson County, Kentucky.The Portal to Texas History
Frederick H. Dyer, A Compendium of the War of the Rebellion (Chicago, 1908), Kentucky section, entries for “Big Hill,” “Skirmish between Big Hill and Richmond,” and “Battle of Richmond or Mount Zion Church,” as reflected in the National Park Service “Kentucky Battles” page.National Park Service
Kentucky Historical Society, Highway Marker 1124, “Big Hill Skirmish,” and related entries in the Kentucky Historical Marker Database; Warrior’s Path marker 697 at Gray Hawk.HMDB+3Kentucky historical marker project+3Kentucky History+3
“The Liberator,” vol. 33, no. 20 (May 15, 1863), containing a letter dated “Gray Hawk, Jackson County, Ky., April 13th, 1863,” scanned at Fair Use Repository.Fair Use Repository
Civil War Governors of Kentucky Digital Documentary Edition, subject files for Thomas H. Wilson, Henry J. Clark, and Samuel Hampton Flanery of Jackson County, all associated with the 7th Kentucky Volunteer Infantry (U.S.).Civil War Governors of Kentucky+2FromThePage+2
“Civil War Soldiers Buried in the Tyner Cemetery,” RootsWeb transcription drawing on the Kentucky Adjutant General’s report and local headstones; Find a Grave memorials for Jackson County Civil War veterans such as Andrew Jackson Isaacs of Company D, 7th Kentucky Infantry.RootsWeb+1
Jackson County Tourism, “Civil War – The Battle of Big Hill Reenactment” and “Big Hill Welcome Center” pages, with map, photographs, and references to Quisenberry, Hafendorfer, Lambert, and the Official Records.jacksoncountytourism+1
A. C. Quisenberry, “The Battles of Big Hill and Richmond, Kentucky, September, 1862,” Register of the Kentucky State Historical Society 16, no. 48 (1918), 7-25; Kenneth A. Hafendorfer, They Died by Twos and Tens: The Confederate Cavalry in the Kentucky Campaign of 1862; D. Warren Lambert, When the Ripe Pears Fell: The Battle of Richmond, Kentucky, August 30, 1862.
H. Muncy, “A Forgotten Shade of Blue: Race, Memory, and the Civil War in Eastern Kentucky,” Ph.D. diss., University of Louisville, 2020, for broader context on Unionism and guerrilla warfare in southeastern Kentucky.ThinkIR