| From Now On | Watchhouse | 3:47 | |
| Joke’s On Me | Rachel Baiman | 2:46 | |
| Kickapoo Creek | Dead Horses | 2:28 | |
| Scattershot | Caitlin Canty | 3:40 | |
| Conveyor Belt | Steve Poltz | 2:34 | |
| I Got You (At the End of the Century) | Chatham County Line | 2:44 | |
| Hello Stranger | Cat Clyde, Jeremie Albino | 2:27 | |
| Giving Back the Best of Me | Jaime Wyatt | 4:38 | |
| Too Stoned to Cry | Andrew Combs | 3:37 | |
| American Poor | Dead Horses | 3:06 | |
| Basil Gone to Blossom | Caitlin Canty | 3:07 | |
| What Made Milwaukee Famous (Has Made A Loser Out Of Me) | Redbird | 3:10 | |
| Roll On My Friend | Pharis & Jason Romero | 3:22 | |
| Far From Home | Western Centuries | 3:52 | |
| Prodigal Daughter | Aoife O'Donovan, Allison Russell | 3:42 | |
| The Flood in Color | Joe Pug | 2:37 | |
| Summertime Mama | Becca Mancari | 2:56 | |
| Chickamauga | Willy Tea Taylor | 5:14 | |
| Garage Flowers | I Draw Slow | 2:58 | |
| Over Alameda | Justin Townes Earle | 4:08 | |
| Live / Die | Nellie Pearl | 3:42 | |
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| Captain's Song (Sorley Boy) | The Orphan Brigade, John Prine | 3:11 | |
| Runnin' | Leah Blevins | 3:57 | |
| Where I'm From | The Steel Wheels | 4:29 | |
| I Thought You Were Somebody Else | Mary Bragg | 3:16 | |
| That's All Right | Dori Freeman | 3:18 | |
| Spittin’ On Fire | Buddy & Julie Miller, Buddy Miller, Julie Miller | 3:05 | |
| How Bad I Wanna Live | Maya De Vitry | 2:53 | |
| Silhouette | Dave Simonett | 2:58 | |
| Lost in the Valley | Caitlin Canty | 3:03 | |
| Adelaide | The Stray Birds | 3:44 | |
| Prettiest Girl | 10 String Symphony | 2:58 | |
| On and On | Dead Horses | 3:37 | |
| Lullaby | Dori Freeman | 3:25 | |
| If I Were a Carpenter (feat. Kelsey Waldon) | JP Harris, Kelsey Waldon | 3:10 | |
| I Don't Wanna Disappear | Malcolm Holcombe, Iris DeMent | 3:53 | |
| Ask Me No Questions | Abigail Lapell | 2:37 | |
| Whim of Iron | Slaid Cleaves | 2:29 | |
| It Ain't Me Babe | River Whyless | 3:40 | |
| Feelin' Good Again | The Brother Brothers | 3:31 | |
| Mama, You Been on My Mind | 10 String Symphony | 2:20 | |
| Wild Heart | Caitlin Canty | 3:17 | |
| Heading Home | Pieta Brown | 3:43 | |
| Hinges | Chatham Rabbits | 3:34 | |
| Wouldn't Be the First Time | Kieran Kane, Rayna Gellert | 2:59 | |
| Roll Julia | The Deep Dark Woods | 3:03 | |
| Barbara's Song | Ian Noe | 3:25 | |
| Mystery | Lukas Nelson and Promise of the Real | 3:33 | |
| Crescent City | I'm With Her, Sara Watkins, Sarah Jarosz, Aoife O'Donovan | 2:59 | |
