The route through the Cumberland Gap was first brought to the attention of travelers by Dr. Thomas Walker,(1) who had been hired to stake out an 800,000-acre grant beyond the Blue Ridge Mountains in Virginia. In 1750, hired by the Loyal Land Company as a surveyor, he and five others recounted the importance of the gap as there was little option to cross the great divide back then. While there were other openings further up the range, they were blocked by more mountains behind and other natural barriers that made going any further too difficult or impossible.(2) This paled to Cumberland Gap, where after crossing it into Kentucky, the traveler was greeted by the Cumberland River and the “Narrows,” which allowed those to travel out of the rugged mountain system of the south. From there on north, it was relatively smooth sailing.
Walker was followed twenty-five years later when Daniel Boone, a renowned pioneer, crossed the gap with 30 others to mark out the Wilderness Trail after the Treaty of Sycamore Shoals was signed, securing a large portion of Kentucky from the Cherokees. The trail was to be marked from Long Island on the Holston River in Kingsport, Tennessee through the Cumberland Gap and to the banks of the Kentucky River, near Richmond, Kentucky.(1)(2) Once there, he would found Fort Boonesborough and eventually hold office.
Between 1776 and 1810, 200,000 to 300,000 settlers crossed the Gap and settle in the Ohio Valley.(1) In 1792, Kentucky became the 15th state, the first west of the Appalachian Mountains, and was soon followed by Tennessee, the 16th, in 1796. By the early 1800s, the Gap was seeing large influxes of new settlers, and was seeing an exodus of livestock and agricultural goods that were being shipped to eastern markets.
Civil War
As the Cumberland Gap was a major transportation artery between the growing frontier and the southeast, control was critical during the Civil War. The ground was held twice by both the Confederates and by the Union,(2)(3) although a lack of railroads in the area limited the influx of soldiers, food and weapons to the area. The first to hold the Gap was the Confederates in August 1861, although this changed on June 18, 1862, when the Union occupied the gap under General Morgan.(3) It changed hands only a few months later on September 17, when Confederate General Stevenson forces the evacuation of Union troops from the Gap as the Confederates’ push into Kentucky’s bluegrass region. Finally, on September 9, 1863, Union forces under General Burnside, accept surrender of Confederate General Frazer’s 2,300-man garrison at the Gap.
Afterwards, Cumberland Gap remained in the Union hands for the duration of the war.
The poor condition of the Wilderness Road also led Ulysses S. Grant to pull most of the troops out from the area in early 1864, citing the number of dead animals and broken wagons as the end result of a nearly impassible highway.(2) No battles were ever fought at the Gap, as the fortifications and terrain proved to be too much for any opposing party to attempt, and those that were garrisoned there saw little action and a lot of reported boredom.(3) Fort Lyon overlooked Virginia and Tennessee, while Fort Rains (Confederate name)/Fort McCook (Union name) overlooked Kentucky.
Dear Father and Mother:
As I can get no letters from home to revive or divert the weary mind, I thought I would put in a few leisure moments in pening you a few lines. Notwithstanding, I have nothing new to communicate. We have some tolerably heavy scouting to do… We have learned that there is no army this side Lexington, Kentucky. Hence we do not apprehend any danger of an attack here soon… We have no war news, everything seems to be still. What can the matter be with the Feds? This time last year, they were tickling us on every rib…
I would prefer being in a country where we could have access to the luxuries of country produce. But we cannot expect to live in clover all the time. Since writing the above we have drawed meal, bacon and rice. This is Robins and Campbells day to cook, they have dinner and supper almost ready (for we take both together)…
Col Heart sent a scout down to Barbersville on the 26th inst. They returned with five yanks. They took six in the town and one started to run when he instantly bit the dust. Write soon hope to get some letters today. Your devoted son,
–Confederate soldier Seth Hannibal Hyatt in a letter home on April 28, 1863
Remains of the fortifications can be seen today via the Pinnacle Road.

Remains of the Union fortification.
Hensley Settlement
an image The Hensley Settlement was a 67-acre self-reliant community along the Cumberland Mountains.(3) In May 1903, 500 acres was purchased by Sherman Hensley (7) and subdivided into 16 parts for the Hensley family and their relatives.(6) They began arriving at the site in 1903-04 and cleared the mountaintop for homes. Constructed of chestnut timber with shake roofs from the cleared forest and stone from the protruding rocks, they provided a stable foundation for which to base their community on. Corn cribs, chicken houses and barns were constructed as well. Within a few years, grist mills, a school, a blacksmith shop, a sorghum mill and whiskey stills joined the original dwellings. At the peak in 1925,(7) the settlement contained 50 to 100 inhabitants and 40 structures.(3) The school closed in December 1947 (6) when only four students and three families remained. Hensley settlement was was occupied until 1951.(5)
Since 1965, the National Park Service has restored three of the farmsteads with their houses, barns, fences and fields, along with the cemetery.(7) The schoolhouse and has been fully rehabilitated to the mid-1940s appearance.

Hensley Settlement.
Modernization
In 1889, a single-track railroad tunnel was constructed from Middlesboro, Kentucky to Cumberland Gap, Tennessee,(1) as part of an effort by entrepreneurs to make the city a major industrial center.(2) Only a few years later, construction began on July 29, 1907 (2) on the Object Lesson Road, a Federal Government demonstration project. It was completed one year later on October 3, 1908. The 14-foot wide road utilized experimental road construction methods, with a new paving type called macadam that consisted of laying and compacting beds of broken stone and sand-clay to provide a suitable driving surface that would not wash out or rut. The road’s name was a term used by the Office of Public Roads in the United States Department of Agriculture for giving engineering assistance while local communities provided the funding.(2)
This was followed by a modern two-lane route, U.S. Route 25E, in the 1920s. Pinnacle Road, which connects the visitors center to the Pinnacle Overlook at 2,440 feet, is a winding two-lane route constrained by a steep roadway and numerous switchbacks. It opened in 1929 to sightseers.(3)
Cumberland Gap National Historical Park was authorized by Congress in 1940, and was established in 1955.(1)
By the late 1950s, U.S. Route 25E’s 2.3-mile route over the Gap was nicknamed ‘Massacre Mountain’ due to the high accident rate, beset by the numerous curves and high volume of traffic.(4) As far back as the 1960s, a tunnel was recommended for bypassing the mountain crossing, and work began in 1979 on a core hole to determine the geology of the mountain. Appropriation battles were fought in congress until funding was finally secured, when at the urging by U.S. Rep. Hal Rogers, a member of the House Appropriations Committee, the Cumberland Gap Tunnel project eventually became part of a highway budget that did not require annual reauthorization. Construction of the new four-lane U.S. Route 25E tunnel began on June 21, 1991 (4) and tunnels joined on July 9, 1992. The tunnel was completed on October 18, 1996.
In April 2004, an extensive restoration of the Cumberland Gap National Historical Park Visitor’s Center was completed.(2) The center, along US 25E in Kentucky, was designed to give the feeling of being in a wilderness, under a canopy of trees and surrounded by lush hardwood forests. For 2007, many of the park roads and parking lots were rehabilitated.
Sources
- Cumberland Gap. N.p.: National Park Service, n.d.
- Shattuck, Tom N. The Cumberland Gap Area Guidebook. 1991. 5th ed. Middlesboro: Bell County Historical Society, 2005.
- Various interpretive markers.
- Cahal, Sherman. “Cumberland Gap Tunnel (US 25E).” Bridges & Tunnels. 2007. 15 Oct. 2007 Article. (Self-reference)
- “Guided Tours.” National Park Service. 27 Sept. 2007. 21 Oct. 2007 Article.
- Schroeder, Joan Vannorsdall. “Time Turned Backward.” Blue Ridge Country. 2004. 21 Oct. 2007 Article.
- “Appalachian Culture.” National Park Service. 10 May 1999. 21 Oct. 2007 Article.



