Cumberland Gap is a natural Passage through the Mountains near the point where Virginia, Kentucky, and Tennessee meet. It was explored and named by Dr. Thomas Walker and Daniel Boone blazed the Wilderness Road through the Gap into Kentucky. During the Civil War it was considered a strategic location held, at times by both Confederate and Union force. Although, there were many skirmishes and the Gap changed hands four times during the war, no major battles actually took place here.

Dr. Thomas Walker first called this” Cave Gap” he later called it Cumberland Gap. He named it after William Augustus, the Duke of Cumberland. William Augustus was a soldier in command in 1745 in Flanders. In the last battle fought he defeated with great slaughter the Highland forces refusing quarters to the wounded and prisoners. Some whose sympathies were with the Highlanders were disappointed that the beautiful mountains of the Appalachians, this Gap, and a most scenic river, should carry his name. It is claimed that many in the early days endeavored to change it to Ouasioto-its Indian name rather than give honor to the Duke of Cumberland.

The  street names in the downtown district are derived from  Scottish heritage.   The majority of the streets or avenues end in one of the following suffixes: lyn, lynn, or wyn.  In Scottish the suffixes lyn, and lynn, mean all the following: (1) a pool or collection of water; (2) a waterfall or cataract; and (3) a steep ravine or precipice. The flow of Gap Creek and the steep terrain around the town  account for suffixes to the names of the streets.  The last suffix, wyn, is derived from the Scottish  word “wynd” which means either: (1) a very narrow street or alley; or (2) to proceed, go or turn.  In light of these definitions, it is understandable why the streets have the names they do.

 Cumberland Gap became postal town in 1803, but it wasn’t until April 1, 1907 that it was actually incorporated and became a town. Cumberland Gap has the only post office that has been in three states (Tennessee, Kentucky, and Virginia). In October 1885 it was changed back to Claiborne County, Tennessee where it remains today.