Looking into the gap from the east
|Elevation||2,392 ft (729 m)|
|Traversed by||U.S. Route 23|
|Location||Letcher County, Kentucky /
Wise County, Virginia,
The Pound Gap of Pine Mountain is on the Virginia/Kentucky border between Jenkins, Kentucky and Pound, Virginia. It served as a passage for early settlers to cross into Kentucky from Virginia. Today, U.S. Route 23 passes through the gap.
In 1750, early surveyors for the Ohio Company, possibly including Christopher Gist, passed through the gap. Many hunters used the gap to cross into Kentucky from Virginia for the next ten years. In 1774, Daniel Boone used the gap to cross into Kentucky, along with Michael Stoner, to warn the land surveyors of a possible attack from the Shawnee Indians. Boone referred to Pound Gap as "Sounding Gap". Circa 1800, some the first pioneer families of eastern Kentucky came to Kentucky through Pound Gap.
In 1834, the General Assembly of Kentucky passed an act to improve the road (one of "Kentucky's Wilderness Traces") from Mount Sterling to Pound Gap to make travel to western Virginia more accessible. The route was widely used to drive livestock (horses, hogs and cattle) into Virginia and other southern markets and was shorter than other routes. The Mount Sterling - Pound Gap road was considered "the longest pre-Civil War state road" 
In 1861 the Confederate States Army regiment under the command of Colonel John S. Williams took control of the gap. On March 16, 1862, 800 Union soldiers from the 42nd Ohio Infantry, under the command of Brigadier General James A. Garfield came from Piketon (present day Pikeville)in the Battle of Pound Gap, forcing the 500 Confederate soldiers (under command of Major John Thompson) after the deadly battle to retreat. General Garfield was the youngest (Union) general of the war, and gained fame from the Battle of Pound Gap.
On May 14, 1892, Dr M.B. Taylor, a.k.a. "The Red Fox" and two confederates, Henan and Cal Fleming, ambushed Ira Mullins, a local moonshiner and his family. The ambush killed five out of seven people who were in the caravan at a rock near Pound Gap now called "Killing Rock". Dr Taylor was hanged at the Wise County Courthouse on October 27, 1893 for the murders. The Red Fox Trail & Killing Rock is now a hiking trail in the Jefferson National Forest.
During the construction of the new section of US 23 in 1998, the "Pine Mountain Pound Gap Thrust Fault" was exposed. "The collision of the North American continent with Africa and Europe more than 275 million years ago formed the Appalachian Mountains and the thrust fault at Pound Gap". Geologist consider the exposed rock to be "one of the most remarkable exposures of rock in the entire eastern United States". On September 26, 1998 Pound Gap was declared Kentucky's first Distinguished Geologic Site by the Kentucky Society of Professional Geologists.
- Pound Gap Kentucky Atlas and Gazetteer. Retrieved on 2010-06-20
- Pound Gap overview Pound Gap High School. Retrieved on 2010-06-20
- Historical Sketches of Southwest Virginia - Online edition Retrieved on 2010-06-20
- Oldest House in the Valley - Chapter One - Online edition Retrieved on 2010-06-20
- The Oldest House in the Valley - Chapter 6 - Online edition Retrieved on 2010-06-20
- Overview of Mount Sterling, Kentucky Kentucky Atlas and Gazetteer. Retrieved on 2010-06-20
- Brothers Once More War Monument Retrieved on 2010-06-20
- Federal Writers' Project (1996). The WPA Guide to Kentucky. University Press of Kentucky. p. 242. Retrieved 24 November 2013.
- Environmental Achievements: Pound Gap Thrust Fault Kentucky Transportation Cabinet. Retrieved on 2010-06-22
- Kuehn, Ken (August 17, 1999). "Pound Gap Roadcut: Kentucky's First "Distinguished Geologic Site".". Geogram. Retrieved 2010-06-22.
- KSPG Awards Retrieved on 2010-06-22