I know that song. 🙂 Cumberland Gap and Cumberland County are in two different parts of the state. Now, if you read down to the next verse in the song, Bearden is in West Knoxville about 25 minutes from my house by Interstate. If you follow Kingston Pike (highway 70) you end up in Kingston where I live.
"Blazing right through Knoxville, out on Kingston Pike
Then right outside of Bearden, there they made the fatal strike
He left the road at ninety, that's all there is to say
The devil got the moonshine and the mountain boy that day"
When you go through the Cumberland Gap from Tennessee (now days though a tunnel in the mountain) you are basically in Middlesboro Kentucky not too far from where TN touches Virginia. Cumberland Gap is a cool place where you can see for miles. We went there with our car club a few years ago. Below is a photo of my wife at the Cumberland gap overlook viewing the town of Middlesboro below.