| Angeline | James McMurtry | 4:04 | |
| Senseless | Chip Taylor | 4:26 | |
| Down By the Riverside | Eliza Gilkyson | 5:24 | |
| Brother Flower | Townes Van Zandt, Kimmie Rhodes | 2:56 | |
| Snowin' on Raton | Gretchen Peters | 4:23 | |
| I Dreamed I Saw St. Augustine | John Doe, The John Doe Folk Trio, Carrie Rodriguez | 3:17 | |
| Swept Away | Missy Raines, Alison Brown, Becky Buller, Molly Tuttle, Sierra Hull | 3:56 | |
| What It Takes | Fred Eaglesmith | 3:57 | |
| Pick Me Up On Your Way Down | Steve Forbert | 2:37 | |
| Lingering On | Tift Merritt | 2:43 | |
| All of Your Stories | Jesse Winchester | 2:33 | |
| I'm Looking for Blue Eyes | Shelby Lynne, Allison Moorer | 2:57 | |
| It's Hard to Sing This Song | Chip Taylor | 4:09 | |
| Emerald Street | Eliza Gilkyson | 3:45 | |
| You Only Believe Me when I'm Lying | Zoe Muth | 3:24 | |
| Never Tire of the Road | Rachel Baiman | 3:45 | |
| Dangerous Fun | Jesse Winchester | 2:05 | |
| Christchurch Woman | Justin Townes Earle | 4:11 | |
| If I Were a Carpenter (feat. Kelsey Waldon) | JP Harris, Kelsey Waldon | 3:10 | |
| Death in Arkansas | Eliza Gilkyson | 4:18 | |
| What Does It Mean to Travel | Mary Chapin Carpenter | 3:09 | |
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| His Eyes | Chip Taylor, Carrie Rodriguez | 4:37 | |
| Morning Trian | David Francey | 2:28 | |
| Farewell to Saint Dolores | Dave Carter, Tracy Grammer | 4:29 | |
| Milly's Café | Fred Eaglesmith | 5:28 | |
| Midnight Train | David Rawlings | 3:18 | |
| Going Away | The Flatlanders | 5:04 | |
| Hide Your Tears | John Hiatt | 3:15 | |
| Think About You | Eliza Gilkyson | 3:23 | |
| Silver Lining | Carl Anderson | 2:30 | |
| Unknown Legend | Caitlin Canty | 3:55 | |
| Hearts Beat and Take a Beating | Forest Sun | 3:16 | |
| Hymn for the Crossing | Amy Speace | 3:36 | |
| Do It | Jesse Winchester | 1:27 | |
| A Hold On Me | Diana Jones | 4:20 | |
| Speakin' of Horses | Chip Taylor | 7:06 | |
| Onto You | Caitlin Canty | 3:30 | |
| It's Too Easy | Dave Rawlings Machine | 3:08 | |
| Cowboy Singer | Dave Carter, Tracy Grammer | 3:44 | |
| Traveling Alone | Tift Merritt | 4:44 | |
| Oh Set a Light | Chip Taylor, Carrie Rodriguez | 3:44 | |
| Fishing With Bill | Bill Morrissey, Greg Brown | 4:32 | |
| That's What Makes You Strong | Jesse Winchester | 3:10 | |
| Afraid | Ted Hawkins | 4:36 | |
| Orphan Girl - Live | Holly Williams, Chris Coleman | 3:52 | |
| I Don't Believe You've Met My Baby | Jerry Douglas | 3:13 | |
| Eastern Sky | Birds of Chicago | 5:40 | |
| To Ohio | Della Mae | 3:38 | |
| Ring Them Bells | Sarah Jarosz | 3:30 | |