| Brokedown Palace | Shinyribs | 6:24 | |
| Quality Time | Iris DeMent | 4:05 | |
| Come See About Me | Tom Rush | 2:50 | |
| Bury Me Under the Weeping Willow | Natalie Merchant | 3:20 | |
| Crossing Muddy Waters | John Hiatt | 4:05 | |
| I Saw A Stranger With Your Hair | John Gorka | 4:03 | |
| It's Too Easy | Dave Rawlings Machine | 3:08 | |
| More Love | Darrell Scott, Tim O'Brien | 4:05 | |
| Willin' | Richard Shindell | 3:15 | |
| There Goes My Love | Caleb Klauder, Reeb Willms | 3:00 | |
| Hermano migrante | Joe Troop, Tim O'Brien | 4:20 | |
| Flat Top Guitar | Ana Egge | 2:50 | |
| Livin' in America | Cahalen Morrison & Eli West | 2:37 | |
| Stewball | Willie Watson | 3:47 | |
| I've Been Gone | Zoe Muth and the Lost High Rollers | 4:28 | |
| They Killed John Henry | Justin Townes Earle | 2:46 | |
| To Get By | Malcolm Holcombe | 4:03 | |
| Boat in the Water | Tom Paxton | 3:02 | |
| Rambling, Gambling Willie | The Lonely Heartstring Band | 3:27 | |
| Way over Yonder in the Minor Key | Dave Carter & Tracy Grammer | 4:14 | |
| This Old Road | Kris Kristofferson | 3:59 | |
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| Down on Penny's Farm | Natalie Merchant | 3:43 | |
| Old Time River Man | Michael Cleveland, Tim O'Brien | 4:52 | |
| Walking Each Other Home | Mary Gauthier | 4:17 | |
| Shoulda Been Done | Kieran Kane, Rayna Gellert | 2:10 | |
| Swimming Song | Lucy Kaplansky | 3:01 | |
| Plow To The End Of The Row | Adrienne Young, Little Sadie | 3:16 | |
| Hard Promises to Keep | Kimmie Rhodes | 4:49 | |
| What Do We Do Now | John Hiatt | 2:58 | |
| Wildwood | Chatham County Line | 3:06 | |
| Short Haired Woman Blues | Dave Rawlings Machine | 6:43 | |
| Lonesome Old River Blues | Dom Flemons | 2:42 | |
| The Road | Amanda Anne Platt & the Honeycutters | 2:39 | |
| Hello Trouble | Bronwyn Keith-Hynes, James Kee, Tim O'Brien | 2:42 | |
| Halleluiah | Reeltime Travellers | 5:30 | |
| Song For A Deck Hands Daughter | James McMurtry | 3:30 | |
| Graceland | The Lonely Heartstring Band | 4:48 | |
| Acadian Driftwood | Richard Shindell | 5:34 | |
| Woody's Rag (with Tony Trischka & Tim O'Brien) | The Del McCoury Band, Tony Trischka, Tim O'Brien | 3:24 | |
| Maggie's Farm | Tim O'Brien | 3:25 | |
| Cold & Bitter Tears | Ted Hawkins | 2:14 | |
| Raleigh And Spencer | Dirk Powell, John Hermann, Tim O'Brien | 2:43 | |
| I Feel The Blues Moving In | Slaid Cleaves | 4:08 | |
| Forever Young | Tim O'Brien | 2:31 | |
| I Wish It Would Rain | Rodney Crowell | 3:28 | |
| Hard Times | Dirk Powell, John Hermann, Tim O'Brien | 3:44 | |
| Letter From Down The Road / And Other Things | Della Mae | 2:51 | |
| Everything Is Broken | Tim O'Brien | 2:57 | |
| Angel Band | Dirk Powell, John Hermann, Tim O'Brien | 4:18 | |
