| Deep End | Steep Canyon Rangers | 2:57 | |
| My Old Kentucky Home | The Local Honeys | 3:46 | |
| Girl, Where You From? | Hannah Juanita | 3:05 | |
| She Ain't Me | Summer Dean | 4:09 | |
| High Country | Brennen Leigh | 3:12 | |
| Toil, Tears & Trouble | The Po' Ramblin' Boys | 2:40 | |
| If I Were a Carpenter (feat. Kelsey Waldon) | JP Harris, Kelsey Waldon | 3:10 | |
| High Sierra | The Brother Brothers, Michaela Anne | 3:07 | |
| Ghosts | John R. Miller | 2:19 | |
| Charlie Pickle | Sad Daddy | 4:16 | |
| Longhair Bluegrass | Robbie Fulks | 4:58 | |
| Blame it on the Bluegrass | Valerie Smith | 3:04 | |
| Little While | The Wooks | 4:18 | |
| Hurt So Bad | Jaime Wyatt, Shooter Jennings | 3:49 | |
| Mama | Brennen Leigh | 2:23 | |
| Woman of God | The Montvales | 3:01 | |
| Take My Ashes to the River | The Po' Ramblin' Boys | 3:22 | |
| Herding Song | Riddy Arman | 2:07 | |
| Ramble on Man | Charlie Marie | 3:21 | |
| When You Change Your Mind | AJ Lee & Blue Summit | 3:36 | |
| Colorado Sky | Cristina Vane | 3:08 | |
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| I've Endured | Kelsey Waldon | 3:19 | |
| I Heard the Bluebird Sing | Conrad Fisher | 2:52 | |
| Blessing in Disguise | Dylan Earl | 4:31 | |
| Think Again | Jaelee Roberts | 4:07 | |
| Forever, You & I | Victoria Bailey | 3:30 | |
| The Down and Back | Willi Carlisle | 1:45 | |
| That Sounds Lonesome | Pitney Meyer, Mo Pitney, Johnny Meyer | 3:01 | |
| West Texas Wind | Alvin Crow, Leeann Atherton, Steven Collins, Brennen Leigh, Dale Watson, Josh Allen, Omar Dykes, Armadillo Road, Redd Volkaert, Amanda Cevallos | 3:30 | |
| Will the Circle Be Unbroken? | Punch Brothers, Gillian Welch, Dave Rawlings | 3:32 | |
| The North Dakota Cowboy | Brennen Leigh | 2:42 | |
| 'Til It Ain't | Shawn Hess | 3:47 | |
| I'd Jump the Mississippi | Caleb Klauder, Reeb Willms | 2:51 | |
| Tried to Ruin My Name | Cory Walker, Sierra Ferrell | 2:23 | |
| Cigarette Trees | The Local Honeys | 2:43 | |
| Grass Valley | Molly Tuttle, Molly Tuttle & Golden Highway | 3:52 | |
| Long And Lonesome Letting Go | Jim Lauderdale, The Po' Ramblin' Boys, Del McCoury | 2:43 | |
| Bridge You're Gonna Burn | Tina Adair | 2:14 | |
| Near Mrs. | Lonesome River Band | 3:11 | |
| You're Gonna Make Me Lonesome When You Go | The Wildmans | 3:43 | |
| Distracted | Summer Dean | 3:38 | |
| Friend of the Devil | Chicken Wire Empire | 5:02 | |
| The Red Flags You Were Waving | Brennen Leigh | 3:07 | |
| Sweet Dreams, Caroline | Forest Sun | 3:15 | |
| Smoky Mountain Girl | Old Crow Medicine Show | 3:45 | |
| Forever Has Come To An End | Buddy & Julie Miller | 2:50 | |
| Gutted | Bella White | 4:06 | |
| Tall Pines | Laurie Lewis | 3:17 | |
| Silver Dollar | Sierra Ferrell | 2:05 | |