All but one of the forty-two tracks (forty-seven songs; duration: 6 hours, 26 minutes) were previously unreleased.

[4] The title of the album comes from the Jerry Garcia and Robert Hunter song of the same name; the version included is from the group's final concert.

After track two, the fifth disc contains live or rehearsal versions of songs that apparently would have gone into the making of the band's never finished 14th studio album.

Of particular interest to many DeadHeads, many of whom are attracted to the Grateful Dead for the often improvisational nature of their live performances, So Many Roads (1965–1995) contains six "jams": In addition, there are many significantly extended tracks, including fourteen tracks over ten minutes long, and two tracks over twenty minutes long ("Dark Star / China Cat Sunflower /The Eleven", on Disc One, and "That's It for the Other One", on Disc Two.

"Passenger" was omitted from the final box set release due to lack of space.