If you're more "blues" than "bluegrass," consider a trip along Highway 61 through Tennessee and Mississippi. It's not so much the road's scenic beauty that makes this trip, as the ability to eat barbecue while catching a jam session or six. The names of the towns you pass are straight out of a Muddy Waters song: Memphis, Clarksdale, Vicksburg and Rosedale.
The last is the setting of the famous Robert Johnson song, "Cross Road Blues," in which, after failing to hitch a ride, the singer sells his soul to the devil for the ability to play the blues. To spend just one more week eating said barbecue and listening to another jam session, you might just consider a similar trade.