Appalachian History
A New Mountain County Caught In A National Crisis
When the Civil War began, Letcher County was a very young place on the Kentucky map. The General Assembly created it in 1842 from parts of Harlan and Perry Counties and fixed the seat at Whitesburg on the North Fork of the Kentucky River.
This was not plantation country. Farms along the creeks from Dry Fork to Rockhouse were small, the enslaved population was limited, and most families depended on mixed farming, timber, and whatever cash they could scrape from livestock and seasonal work. Yet Letcher County sat in a crucial position between Bluegrass markets to the northwest and Virginia’s railroads and saltworks to the southeast.
The county was drawn into statewide politics even before the first shots were fired. In May 1861 the Commonwealth formally organized the Kentucky State Guard. Lists of officers published at the time show Major Joseph Cornett of Whitesburg as the State Guard commander for Letcher County. Men who drilled under Cornett’s command soon faced hard choices about whether to follow the Union or the new Confederate government.
Roads, Ridges, And The Making Of A Border
Geography gave Letcher County a strategic weight out of proportion to its population. Pine Mountain and Black Mountain hemmed in the valleys, but at Pound Gap the ridge broke just enough to let a road through. The old route from Mt. Sterling to Hazard and Whitesburg climbed out of the Kentucky interior, crossed Pine Mountain at Pound Gap, then dropped into Wise County, Virginia, on the way to Abingdon and the East Tennessee and Virginia Railroad.
Within the county, Confederate officers and local residents used the name Rebel Trace for the main military road that wound from the gap down Rockhouse Creek and across the hills toward the headwaters of the North Fork. Modern researchers, drawing on wartime maps, diaries, and local memory, have reconstructed the path that led from the crest into Letcher County, through Rockhouse and Colly, and past scattered farmsteads and mills.
In a county with few towns, roads and creeks effectively were the public square. Control of the route over Pine Mountain and along the Rebel Trace meant control of who and what entered Letcher County. That is why armies that seemed small on the national stage mattered so much here.
Garfield, Marshall, And The Mountain Front
The first large military presence in Letcher County came during the winter of 1861 and 1862. Confederate Brigadier General Humphrey Marshall built up a force in the Big Sandy valley, using the mountains as a shield while he tried to organize support in eastern Kentucky. Brigadier General James A. Garfield, recently appointed to federal command, marched his mixed brigade up the Sandy and fought Marshall at Middle Creek in January 1862.
After Middle Creek, Marshall fell back toward Pound Gap and the Letcher County border. From Federal headquarters Garfield reported that Marshall’s men were camped “at or near Pound Gap” and that he intended to push them out to remove “the menace to Eastern Kentucky.” Those reports, preserved in Series I, Volume 7 and Volume 10 of the Official Records of the War of the Rebellion, mark the beginning of an extended struggle over Letcher County’s front door.
On 16 March 1862 Garfield led roughly six or seven hundred Union troops against the Confederate camps around the gap. In his detailed report he described a grueling ascent in snow, difficulty keeping his columns together on the ridge, and a final advance that sent about five hundred Confederate defenders fleeing into Virginia. His men burned about sixty log huts and destroyed wagon trains and commissary stores. They carried off muster rolls and a packet of Humphrey Marshall’s letters that had been left in camp.
Marshall’s own official report, written from Lebanon, Virginia, quoted Major John B. Thompson, who claimed he had “fought them nearly an hour and a half” before being forced to withdraw and insisted that Garfield’s strength was closer to twenty five hundred infantry and one hundred cavalry.
Compilers like Frederick H. Dyer later reduced this contested fight to a single line in their chronological tables: “Pound Gap, Ky., March 16, 1862.” For Letcher County, however, Garfield’s expedition did not end the war. It only marked the beginning of three years in which the county seat, the hollows, and even the graveyards became part of the front.
Whitesburg: A Few Houses And One Large Hospital
To see how, it helps to shift our focus from the crest of Pine Mountain down to Whitesburg.
Edward O. Guerrant, a young Kentucky physician who served on Humphrey Marshall’s staff, kept a diary that later appeared in print as Bluegrass Confederate. In one passage he described reaching Whitesburg, “a town with a few houses and one large hospital,” at the mouth of Sandlick Branch on the North Fork of the Kentucky River.
Those two short phrases show how the war transformed the new county seat. Population and commerce were limited in the early 1860s, but the town suddenly hosted a substantial Confederate hospital. Guerrant’s entries and later local research suggest that wounded and sick soldiers came to Whitesburg from fighting across eastern Kentucky and southwestern Virginia and that a Confederate cemetery grew up nearby as men died far from their home counties.
Other Confederate accounts, such as George Dallas Mosgrove’s Kentucky Cavaliers in Dixie, describe patrols and picket posts along Rockhouse, Colly, and the North Fork. Together, these sources make it clear that Letcher County was not an empty space behind the lines. It was a landscape of camps, hospitals, and recruitment depots that held Marshall’s scattered army together.
Letcher County’s Soldiers In Blue And Gray
The rosters preserved in the Report of the Adjutant General of the State of Kentucky and in federal Compiled Military Service Records reveal how deeply the conflict penetrated Letcher’s households. Even a brief look at those records shows long lists of men from Letcher County serving on both sides.
On the Confederate side, many county men joined what became the 13th Kentucky Cavalry, C.S.A., better known as Caudill’s Army. A detailed regimental study, 13th Kentucky Cavalry, C.S.A.: Caudill’s Army, published by the Ben E. Caudill Camp in Whitesburg, reproduces rosters and service sketches that show enlistments from Dry Fork, Rockhouse, Millstone, and other Letcher communities. Companies mustered at Whitesburg and served along Pound Gap, the Rebel Trace, and in nearby Virginia.
A separate online roster of Caudill’s regiment, based on those same service records, notes for example a cluster of men who enlisted at Whitesburg in 1862, including several members of the Caudill family and their neighbors.
Union service was just as significant. Men from Letcher County appear in the ranks of federal Kentucky infantry and cavalry regiments and in local Home Guard units. Regimental summaries for the 22nd and 45th Kentucky record patrols “from Cumberland Gap to Louisa” and duty “near Pound Gap” or along the eastern Kentucky front, work that necessarily brought them through Letcher County.
The names on these rosters match the surnames in county histories and modern phone books. The Civil War in Letcher County was not an abstract debate over states’ rights. It was a war in which cousins rode under different flags while their parents tried to protect cornfields, livestock, and small patches of bottom land along the creeks.
Skirmishes, Raids, And A Long War On The Home Front
After Garfield’s 1862 expedition, the Official Records and federal compendia list a series of smaller actions tied to Letcher County. Dyer’s Compendium records a “skirmish near Pound Gap, Ky., May 9, 1864.” The Kentucky National Guard’s survey, The Paper Trail of the Civil War in Kentucky, summarizes the county’s wartime experience in a concise section titled “Civil War 1861–1865 in Letcher County.”
That report notes that Confederate and Union forces that passed through strategic Pound Gap “visited the new county,” that Brigadier General Garfield and about seven hundred Union troops drove some five hundred Confederates from the gap on 16 March 1862, that other skirmishes took place near Whitesburg late in 1863, and that on 1 June 1864 John Hunt Morgan’s cavalry dislodged a Union force from the gap during his last Kentucky raid before riding on to Mt. Sterling, Lexington, and Cynthiana.
County histories and local memory flesh out what these terse summaries meant on the ground. Isaac A. Bowles’s History of Letcher County, Kentucky describes the burning of the courthouse, the activity of guerrilla bands, and the long shadow of wartime feuds in local politics. William T. Cornett’s later pamphlet, Letcher County, Kentucky: A Brief History, likewise emphasizes how the war and its aftermath shaped voting patterns and county leadership well into the late nineteenth century.
For residents, each new column of cavalry or infantry did not simply pass through on the way to a named battle. Every passage meant requisitioned livestock, destroyed fences, and the risk that helping the “wrong” soldiers could bring retaliation when the balance of power shifted again.
Black Letcher Countians In A Divided County
Although Letcher County never resembled the plantation belts of central Kentucky, Black men and women lived here as enslaved people and as free residents both before and after the war. The Notable Kentucky African Americans database pulls together census and tax records for the county under the heading “Letcher County (KY) Enslaved, Free Blacks, and Free Mulattoes,” and links those entries to discussions in The Kentucky Encyclopedia and county histories.
These sources show that a small number of enslaved people lived along the creeks and that a handful of free Black families appear in the records as laborers, servants, or craftspeople. Emancipation, military service, and postwar migration altered that landscape, but Black Letcher Countians remained part of the story as miners, farmers, and in some cases veterans of the Union army.
The documentary trail here is thinner than it should be. Pension files, scattered obituaries in the Mountain Eagle, and oral histories hint at Black veterans and their families in and around Whitesburg. Bringing those lives into clearer focus is an important task for future work on Letcher County’s Civil War experience.
Memory On Pine Mountain And Along The North Fork
Today, drivers on US 23 and 119 cross Pine Mountain in a matter of minutes. Near the summit, just inside the Kentucky line above Jenkins, the Pound Gap Civil War Memorial marks the history that once made this stretch of road the focus of statewide anxiety.
The granite “Brothers Once More” monument at the overlook features portraits of Abraham Lincoln and Jefferson Davis on one face and, on the other, James A. Garfield and John Hunt Morgan. Text on the stone and accompanying markers summarize Garfield’s 1862 victory, Morgan’s 1864 raid, and the broader Civil War story of Letcher County.
Historical Marker 510, erected by the Kentucky Historical Society and documented through the ExploreKYHistory project, calls Pound Gap a natural route discovered by explorer Christopher Gist on 1 April 1751 and notes that “Brig. Gen. Garfield and 700 Union troops forced 500 CSA men from here Mar. 16, 1862” and that Morgan’s raiders later dislodged Union forces here on their way across Kentucky.
Nearby markers remember Caudill’s Army, the Pound Gap Massacre of 1892, and later chapters in local history. Together, they show how Letcher Countians in the twentieth and twenty first centuries chose to present their Civil War past to visitors and to themselves, often stressing reconciliation between former enemies without erasing the very real conflicts that once divided the county.
Down in the valleys, Whitesburg’s historic downtown and the bridges over the North Fork still follow the same basic lines that soldiers and civilians used during the 1860s. Modern tourism materials that promote “historic downtown Whitesburg” and the surrounding river scenery unknowingly echo older descriptions of the town as a small cluster of buildings on an important crossing.
Why Letcher County’s Civil War Story Matters
Focusing on Letcher County changes how we see the Civil War in the Appalachian borderlands. Instead of treating Pound Gap as an isolated skirmish site on the Kentucky Virginia line, we see a whole county that became a contested corridor, a hospital district, a recruiting ground, and a home front under constant pressure.
Primary sources like the Official Records, Guerrant’s diary, Mosgrove’s reminiscences, and the rosters preserved in the Adjutant General’s reports and Caudill’s Army volume show Letcher County residents making choices and living with the consequences in real time. Secondary works such as Bowles’s county history, Cornett’s brief narrative, the Paper Trail project, and the Kentucky Historical Society’s markers help us connect those choices to the larger arc of the war in Kentucky.
To walk the overlook at Pound Gap or the streets of Whitesburg today is to move through the same landscape that shaped those decisions. The war in Letcher County was never only about a mountain pass. It was about families along the Rebel Trace who watched flags and uniforms change while the creeks and ridges stayed in place.
Sources & further reading
Official Records of the War of the Rebellion, Series I, especially Volumes 7 and 10 (Part I), for correspondence on Humphrey Marshall’s eastern Kentucky operations and the full reports of the March 16, 1862 action at Pound Gap by Brig. Gen. James A. Garfield and Brig. Gen. Humphrey Marshall. Digitized through Cornell University’s Making of America collection and other repositories:
https://ebooks.library.cornell.edu/m/moawar/waro.html kynghistory.ky.gov+1
Frederick H. Dyer, A Compendium of the War of the Rebellion (Des Moines, 1908), entries for “Pound Gap, Ky., March 16, 1862” and related eastern Kentucky operations, available via Internet Archive:
https://archive.org/details/08697590.3359.emory.edu/page/100/mode/2up Vdoc
Report of the Adjutant General of the State of Kentucky, 1861–1866, for rosters, casualty lists, and State Guard officer appointments for Letcher County, digitized through the Kentucky Digital Library:
https://digital.library.louisville.edu/digital/collection/p16302coll6/id/2461 kynghistory.ky.gov+1
Edward O. Guerrant, Bluegrass Confederate: The Headquarters Diary of Edward O. Guerrant, M.D., ed. William C. Davis and Meredith L. Swentor (Baton Rouge: Louisiana State University Press, 1999), with excerpts and discussion in “Contested Borderland: The Civil War in Appalachian Kentucky and Virginia”:
https://vdoc.pub/documents/contested-borderland-the-civil-war-in-appalachian-kentucky-and-virginia-7klsthf2aqh0TRACE+1
George Dallas Mosgrove, Kentucky Cavaliers in Dixie: Reminiscences of a Confederate Cavalryman (Louisville, 1895), available at Internet Archive:
https://archive.org/details/kentuckycavalier00mosg/page/n5/mode/2up Vdoc
13th Kentucky Cavalry, C.S.A.: Caudill’s Army, Ben E. Caudill Camp No. 1629, SCV, Whitesburg, Kentucky, 2013, with catalog information and partial preview at WorldCat and Google Books:
https://search.worldcat.org/title/960931851
https://books.google.com/books?id=h3iaoAEACAAJ WorldCat+2Google Books+2
Online roster of the 13th Kentucky Cavalry, C.S.A., with enlistment data for Letcher County men, at Yeahpot:
https://yeahpot.com/military/13th_kentucky_cavalry_csa_roster.htm yeahpot.com+1
“The Paper Trail of the Civil War in Kentucky, 1861–1865,” Kentucky Heritage Council and Kentucky National Guard, PDF with section “Civil War 1861–1865 in Letcher County”:
https://kynghistory.ky.gov/Our-History/History-of-the-Guard/Documents/ThePaperTrailoftheCivilWarinKY18611865%202.pdf kynghistory.ky.gov+2facebook.com+2
Isaac Anderson Bowles, History of Letcher County, Kentucky: Its Political and Economic Growth and Development (Hazard, 1949), available via Internet Archive:
https://archive.org/details/historyofletcher00bowl epdf.pub
William T. Cornett, Letcher County, Kentucky: A Brief History (Prestonsburg, 1967). Often cited in later state and local studies; limited library catalog entry at WorldCat:
https://www.worldcat.org/title/letcher-county-kentucky-a-brief-history/oclc/2577384 epdf.pub
ExploreKYHistory, “Pound Gap” (Historical Marker 510), Kentucky Historical Society:
https://explorekyhistory.ky.gov/items/show/237 explorekyhistory.ky.gov+2explorekyhistory.ky.gov+2
Kentucky Historical Society Historical Marker Database, “Pound Gap” and county marker listings for Letcher County:
https://secure.kentucky.gov/kyhs/hmdb/MarkerSearch.aspx?county=67&mode=County secure.kentucky.gov+1
Historical Marker Database (HMdb) entries for “Pound Gap” and “Caudill’s Army” at Pound Gap:
https://www.hmdb.org/m.asp?m=97150
https://www.hmdb.org/m.asp?m=90803 HMDB+2HMDB+2
Notable Kentucky African Americans Database, entry “Letcher County (KY) Enslaved, Free Blacks, and Free Mulattoes”:
https://nkaa.uky.edu/nkaa/items/show/1148 epdf.pub
“The Pound Gap Civil War Memorial (on Pine Mountain),” The Kentucky Wildlands:
https://www.explorekywildlands.com/listing/pound-gap-civil-war-memorial-%28on-pine-mountain%29/1259/
“Historic Downtown Whitesburg,” Kentucky Tourism:
https://www.kentuckytourism.com/explore/historic-downtown-whitesburg-4034
Wikimedia Commons image of the Pound Gap historical marker on Pine Mountain:
https://commons.wikimedia.org/wiki/File:Pound_Gap_historical_marker.jpg commons.wikimedia.org