| In Chicago | Amy Speace | 3:42 | ||
| Better Times Will Come | Diana Jones | 2:53 | ||
| Wondering | Teddy Thompson, Kelly Jones | 2:38 | ||
| Birthday Song | Amanda Anne Platt & the Honeycutters | 4:15 | ||
| These Hills | Iris DeMent | 3:40 | ||
| Lonely Street | Bap Kennedy | 4:16 | ||
| You're Still On My Mind | Carrie Rodriguez | 2:56 | ||
| Shotgun Hearts | Amy Speace, The Orphan Brigade | 4:46 | ||
| Detroit or Buffalo | Amanda Shires | 4:08 | ||
| Love, The Magician | Dave Carter, Tracy Grammer | 4:18 | ||
| Next Best Western | Richard Shindell | 4:17 | ||
| Different Kind Of Gone | Mary Gauthier | 3:41 | ||
| Someday Soon | Lucy Kaplansky | 4:01 | ||
| Birmingham Sunday | Rhiannon Giddens | 6:13 | ||
| Maiden Voyage | Caroline Herring | 3:41 | ||
| The Trumpet Vine | Kate Wolf | 4:29 | ||
| Oh Abraham | John Gorka | 4:21 | ||
| I Should Have Said | Bap Kennedy | 3:17 | ||
| Crocodile Man | Dave Carter, Tracy Grammer | 3:02 | ||
| Never Be Fooled Again | Zoe Muth | 7:51 | ||
| Numbered Doors | Lori McKenna | 3:44 | ||
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| My Bucket's Got a Hole in It | Chip Taylor, Carrie Rodriguez | 2:32 | ||
| Every Pilgrim Needs a Highway | Craig Market, Thomm Jutz | 3:32 | ||
| Farewell to Saint Dolores | Dave Carter, Tracy Grammer | 4:29 | ||
| River Girl | Kelley Mickwee | 4:47 | ||
| Jackie's Train | Mary Gauthier | 3:20 | ||
| Buckets of Rain - Live | Neko Case | 2:48 | ||
| Dreams Like This | Greg Trooper | 3:42 | ||
| Pilgrim (You Can't Go Home) | Dave Rawlings Machine | 7:57 | ||
| Free Again | Tim O'Brien, Darrell Scott | 4:30 | ||
| Gospel Shoes | Watchhouse | 4:05 | ||
| One Red Rose | Iris DeMent | 3:07 | ||
| This Will Be Our Year | Bruce Robison, Kelly Willis | 2:22 | ||
| Willin' | Richard Shindell | 3:15 | ||
| April Come She Will | Tracy Grammer | 2:06 | ||
| When My Work Is Done | Stephen Fearing | 2:48 | ||
| The Way It Dimmed | Amanda Shires | 2:11 | ||
| Bye Bye Montreal | Amelia Curran | 2:46 | ||
| Oh Susanna | The Be Good Tanyas | 4:20 | ||
| Deep Water | Amy Helm | 4:08 | ||
| Willow Tree | Diana Jones | 2:53 | ||
| Arrow | Cheryl Wheeler | 4:20 | ||
| Last Of The Hobo Kings | Mary Gauthier | 5:50 | ||
| Before You Leave | Mary Gauthier | 3:42 | ||
| The Maker | Willie Nelson | 5:08 | ||
| Kind Woman | Chris Smither | 3:50 | ||
| Dim Star Of The Palisades | Birds of Chicago | 2:58 | ||
| Holding Up the Sky | Buddy & Julie Miller | 3:09 | ||
| Ring Them Bells | Sarah Jarosz | 3:30 | ||
