I never was a huge fan of jam bands. The Grateful Dead? Never listened to any of their records from beginning to end and have never been to a show. Phish? Meh. But, there was a time in the mid to late 90's and early aughts that I used to listen to DMB all the time, particularly their debut album and Busted Stuff from 2002. Much of the material from this album actually dates back to 2000 but was abandoned at that time and then eventually re-recorded for the 2002 release.
Incredibly (and thankfully) 'Where Are You Going' was one of the new tracks recorded for the record. I would start there as the notes he elicits from his 12-string guitar are as beautiful as you'll ever hear. Going in order, I'd move on to 'Grace Is Gone,' 'Digging A Ditch' and 'Bartender.' Diehard DMB fans will have a bone to pick with these selections I'm sure, so give the whole album a spin and see what catches your ear.