Darius Rucker - Wagon Wheel Lyrics Meaning

The singer although from the South is currently in the north. After realizing how bad it is up there, he realizes that the grass is not greener on the other side. He aspires to get back down south by hitchhiking and to rekindle a relationship with his previous sweetheart. By “if I die in Raleigh, at least I will die free,” is a direct connotation to the Confederate States versus the Union during the civil war.. the confederates fought for freedom from the federal government.. although the war having long been over, it still resonates with him, considering he’s running away from the North where he was currently residing, and wants to be “free,” of all his dislikes of the region. He wants to get back to the south.. to the way things were, and most importantly out of the North because he does not like it.