| Milwaukee Blues | Appalachian Road Show | 3:44 | ||
| The Honky Tonk Downstairs | The Po' Ramblin' Boys | 2:49 | ||
| Cannonball | Sister Sadie | 3:56 | ||
| Wildflowers | Mark O'Connor, Maggie O'Connor | 4:23 | ||
| Whither You Roam | Chris Jones & The Night Drivers | 2:18 | ||
| Ride Away | Della Mae | 3:08 | ||
| Crossing County Lines | The Dirty Grass Players | 2:40 | ||
| Cold Wind | Mile Twelve | 2:35 | ||
| Colorado Bound | Stillhouse Junkies | 3:48 | ||
| Losing You Blues | Sister Sadie | 2:48 | ||
| Trip Around The Sun | Bronwyn Keith-Hynes, Dierks Bentley | 4:20 | ||
| Natural to Be Gone | The Travelin' McCourys | 3:37 | ||
| Ramblin' Heart | Mountain Heart | 2:58 | ||
| You Can't Stop Me from Staying | Jaelee Roberts | 3:16 | ||
| I May Be A Fool | Sister Sadie | 2:12 | ||
| It's Just A Road | The Boxcars | 2:47 | ||
| Jericho | Mile Twelve | 4:18 | ||
| Way Downtown | Rob Ickes & Trey Hensley, Rob Ickes, Trey Hensley | 3:12 | ||
| The Whole of the Moon | The Travelin' McCourys | 4:42 | ||
| Allegheny Town | Missy Raines | 3:32 | ||
| This Time | The Caleb Daugherty Band | 2:26 |