Justin,
Being the C/W fan you are, have you ever heard or gone to FanFare in Nashville? I was there this past June - amazing since I've never been a huge C/W person. However, it was really a great time and I actually enjoyed a lot of the music. Some of those people are just Rock'n Roll with cowboy hats, IMO.
Saw Montgomery Gentry, Brooks & Dunn, Alan Jackson, Sara Evans, Brad Paisley, and a whole bunch of performers I'd never heard of. Worth the trip if you've never attended - I enjoyed the comradery of the fans too. The drive was a killer tho!