[2] 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.

[6] The Mount Sterling - Pound Gap road was considered "the longest pre-Civil War state road" [7] The route roughly follows modern day KY 11 from Mount Sterling to Clay City, then KY 15 from Clay City to Whitesburg, and finally US 119 from Whitesburg, along the Kentucky River, to its headwaters in Pound Gap.

Taylor, also known as "The Red Fox", and two confederates, Henan and Cal Fleming, ambushed Ira Mullins, a local moonshiner and his family.

On November 30, 1927, Leonard Woods, a black coal miner and resident of Jenkins, Kentucky, was lynched on the Virginia-Kentucky border at Pound Gap.

On the night of the lynching, a crowd estimated between 400 and 500 surrounded the Kentucky jail Woods was held in and demanded he be released to their custody.

The crowd then transported Woods to a wooden structure located in Pound Gap adjacent to the recently constructed US 23 highway.

"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".