Jimmy Buffet at Riverbend in Cincinatti is great every year but seeing Ralph Stanley and the Clinch Mountain Boys on a glorious summer night, playing from a makeshift stage in a field was the single greatest.
Once when I was an undergrad at the University of Kentucky, I was dating a girl on the student government concert committee. Johnny Cash played a show there. I got to watch from backstage (due to my abject begging for her to let me) and meet the man in black. Hell of a show and a nice guy.