| In Chicago | Amy Speace | 3:42 | |
| Uphill | Lori McKenna | 3:01 | |
| Farewell to Bitterroot Valley | Dave Carter, Tracy Grammer | 2:37 | |
| Pretty Bird (with Laurie Lewis) | Linda Ronstadt, Laurie Lewis | 2:38 | |
| Tenderhearted | Sara Watkins | 2:54 | |
| Rise Up Singing | Daisy May | 3:35 | |
| Cactus Tree | Caroline Herring | 4:31 | |
| Let The Good One Go | Courtney Marie Andrews | 2:51 | |
| Love Soldiers On | Tift Merritt | 2:59 | |
| Don't Want to Die in the Storm | Anna & Elizabeth | 1:54 | |
| Ten Year Night | Lucy Kaplansky | 5:12 | |
| Let No Man Steal Your Thyme | Traditional, Carey Mulligan, Michael Sheen | 2:05 | |
| Dear Someone | Red Molly | 2:01 | |
| Traveling Alone | Tift Merritt | 4:44 | |
| Pretty Little Miss | Joan Shelley, Doug Paisley | 3:04 | |
| I Had Something | Lucy Kaplansky | 4:16 | |
| Someone's Arms | Eilen Jewell | 3:49 | |
| This Will Be Our Year | Bruce Robison, Kelly Willis | 2:22 | |
| Midnight on the Water | Caroline Herring | 4:04 | |
| Today's The Day | Lucy Kaplansky | 3:11 | |
| Blues in D | Kate & Anna McGarrigle | 2:43 | |
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| If I Could Make You My Own | Dori Freeman | 3:22 | |
| Keep Your Hat on Jenny | Chip Taylor, Carrie Rodriguez | 3:26 | |
| Chase Wild Horses | Kim Richey | 3:42 | |
| All The Pretty Little Houses | Caroline Herring | 3:06 | |
| For Free | Tift Merritt | 4:57 | |
| Little Pink | Kaia Kater | 4:01 | |
| The Ransom | Madison Violet | 3:37 | |
| When the Roses Bloom Again | Laura Cantrell | 4:05 | |
| Don't Explain | Billie Holiday, Simone Dinnerstein, Tift Merritt | 4:11 | |
| River Alone | Caitlin Canty | 4:54 | |
| I Saw A Stranger With Your Hair | John Gorka | 4:03 | |
| Ern & Zorry's Sneakin' Bitin' Dog | Dori Freeman | 2:10 | |
| Urge for Going | Joni Mitchell | 5:08 | |
| Wayfaring Stranger | Traditional, Tift Merritt | 3:38 | |
| It Must Be Someone Else’s Fault | Courtney Marie Andrews | 3:18 | |
| Catch the Wind | Kimmie Rhodes | 3:14 | |
| Willow Tree | Diana Jones | 2:53 | |
| Flee as a Bird | The Secret Sisters | 2:35 | |
| Life is Fine | Tom Rush | 3:39 | |
| Wish for You | Allison Moorer | 3:24 | |
| Guinevere | Lucy Kaplansky | 4:20 | |
| Black Irish Indian | Cherokee Rose | 3:17 | |
| The Bird & The Rifle | Lori McKenna | 4:24 | |
| Adieu False Heart | Linda Ronstadt, Ann Savoy | 3:34 | |
| Way Out West | Mary McCaslin | 4:13 | |
| Lay Down Your Weary Tune | Tim O'Brien | 3:28 | |
| Who Carried You | Malcolm Holcombe | 3:31 | |
| Stars Fell On Alabama | Tara Nevins | 2:56 | |