| Heading Home | Pieta Brown | 3:43 | |
| Homeland Refugee | The Flatlanders | 3:58 | |
| Lorraine | Lori McKenna | 4:13 | |
| Wasteland of the Free | Iris DeMent | 5:15 | |
| Downbound Train | Joe Pug | 4:05 | |
| The Road | Amanda Anne Platt & the Honeycutters | 2:39 | |
| I Follow Rivers | Jason Isbell, Amanda Shires | 2:37 | |
| Brightest Star | Lilly Hiatt | 3:07 | |
| Heart Like a Wheel | Zoe Muth and the Lost High Rollers | 3:37 | |
| Crazy | Lydia Loveless | 5:52 | |
| River Girl | Kelley Mickwee | 4:47 | |
| New York | Amanda Anne Platt & the Honeycutters | 4:17 | |
| Highwomen | The Highwomen, Brandi Carlile, Natalie Hemby, Maren Morris, Amanda Shires, Yola | 3:32 | |
| Southern Man | Caitlin Canty | 3:43 | |
| Mineral Wells | Amanda Shires | 4:11 | |
| The Asp and the Albatross | Freakwater | 3:10 | |
| Borderline | Eliza Gilkyson | 2:42 | |
| 18 Wheels | Fred Eaglesmith | 5:01 | |
| First Air of Autumn | Drive-By Truckers | 3:30 | |
| Santa Fe | Eilen Jewell | 4:32 | |
| Only the Song Survives | John Hiatt | 4:00 | |
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| South | Blackie & The Rodeo Kings | 4:24 | |
| Music You Mighta Made | Gurf Morlix | 4:37 | |
| Angel from Montgomery | Bonnie Raitt | 4:11 | |
| Basil Gone to Blossom | Caitlin Canty | 3:07 | |
| Mama Bake a Pie (Daddy Kill a Chicken) | Drive-By Truckers | 3:19 | |
| Bye Bye Montreal | Amelia Curran | 2:46 | |
| If I've Only One Time Askin' | Daniel Romano | 2:54 | |
| White Feather | Amanda Shires | 3:34 | |
| Oyster and Pearl | Amy Ray, Phil Cook, Brad Cook, Justin Vernon | 4:00 | |
| Mercy | Po' Girl | 4:56 | |
| I Hear Them All | Dave Rawlings Machine | 2:27 | |
| Flycatcher Jack and the Whippoorwill's Song (feat. Fats Kaplin) | Kieran Kane, Kevin Welch, Fats Kaplin | 4:01 | |
| Empty Cups | Amanda Shires | 3:58 | |
| Bottomless Mimosas | Sam Outlaw | 3:46 | |
| Redesigning Women | The Highwomen, Brandi Carlile, Natalie Hemby, Maren Morris, Amanda Shires | 2:54 | |
| My Love Follows You Where You Go | Lori McKenna | 3:34 | |
| Back in My Day Blues | Otis Gibbs | 3:14 | |
| Sure Feels Good Anyway | Amy Ray | 4:30 | |
| Cherry Red Wine | Max Gomez | 3:51 | |
| New Damnation Alley | Malcolm Holcombe, Iris DeMent | 4:20 | |
| Something To Me | Tift Merritt | 4:09 | |
| Oh, Sister [Feat. Courtney Marie Andrews] | Logan Ledger, Courtney Marie Andrews | 3:40 | |
| Where I Am Now | Shelby Lynne | 3:40 | |
| Remember Wild Horses | Birds of Chicago | 4:46 | |
| Bottom Of The World | Alejandro Escovedo | 3:04 | |
| Another Free Woman | Blackie & The Rodeo Kings, Sara Watkins | 3:30 | |
| I Am Your Tambourine | Tift Merritt | 3:44 | |
| Dust of Daylight | Son Volt | 3:06 | |