The Cumberland Gap is a pass through the Cumberland Mountains where Virginia, Kentucky and Tennessee meet. In 1750 the Loyal Land Company of Virginia sent Thomas Walker to look for a way west. He went through the gap and gave the Cumberland name to the mountain, after the Duke of Cumberland. In 1775 the land speculator Richard Henderson paid Daniel Boone to blaze a trail through the gap, and between 200,000 and 300,000 settlers later traveled west on that route, the Wilderness Road. During the Civil War, Union and Confederate troops traded control of the gap in 1862 and 1863.
The song circles the place without telling its story in order. Some texts include verses about the gap’s exploration or its Civil War occupations; one long Kentucky version published in 1931 names the generals and the burning of supplies. The verse that marks the song is a call to the boys to lie down and take a nap, with Cumberland Gap as the place name that answers it. Horace Kephart heard a snatch of it from a mountain companion and called it a song “of modern and local origin” in Our Southern Highlanders (1913). The tune is older: it was widely played by fiddlers across the upland South and dates well back into the 19th century. Bascom Lamar Lunsford thought it was a sped-up form of the tune of the ballad “Bonnie George Campbell.”
Many sung versions are domestic and comic rather than historical. The singer heads back to the gap to see his family, plans to buy a farm and grow sweet potatoes, asks an old aunt to guard his jug and threatens trouble if it is gone, and wakes up sober in the Cumberland Gap after a nap.
The first recording was an instrumental. Uncle Am Stuart, a fiddler from Morristown, Tennessee, made it in New York around 7 July 1924, at a session of fourteen sides for Vocalion with Gene Austin on banjo; it was issued on Vocalion 14839, backed with “Grey Eagle.” Stuart died in 1926. Land Norris made the first sung version later in 1924, issued on OKeh 40212, and Gid Tanner and Riley Puckett recorded it for Columbia the same year. Fiddlin’ Powers & Family also recorded it for Victor in 1924, though their version was not issued. Woody Guthrie set his “End of My Line” to the same tune, and Don Reno and Red Smiley recorded it for King around 1956. In Britain, Lonnie Donegan’s skiffle version on Pye Nixa reached No. 1 on the singles chart in April 1957 and stayed there for five weeks.