| The Trouble with Wanting | Joy Williams | 3:55 | |
| For Emily Asleep | Anna Tivel | 3:27 | |
| The Bear (Trio) | Matt the Electrician | 4:24 | |
| All the Beds I've Made (Acoustic) | Caroline Spence | 3:33 | |
| Banshee Moan | Shannon McNally | 4:01 | |
| She Don't Like Roses | Christine Kane | 4:47 | |
| American Poor | Dead Horses | 3:06 | |
| Jam | Feral Mouth, Sara Watkins | 9:22 | |
| Old Mountain Line | Po' Girl | 2:10 | |
| Kalamazoo | The Show Ponies | 5:53 | |
| Backstreets | The Weepies | 3:42 | |
| Round Prairie Road | Jamestown Revival | 3:54 | |
| The Expert | Rose Cousins | 3:33 | |
| Maria | I Draw Slow | 3:07 | |
| Heavenly Track | Kaia Kater | 3:00 | |
| Endless Running Out of Time | The Secret Sisters | 3:58 | |
| Adelaide | The Stray Birds | 3:44 | |
| Where I Stood | Dori Freeman | 3:02 | |
| Traveling Alone | Tift Merritt | 4:44 | |
| Take Me Home | Free the Honey | 3:32 | |
| The Only Pretty Thing in Texas | Kate Rhudy | 4:28 | |
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| Slow Dancer (Acoustic) | Caroline Spence | 3:59 | |
| On and On | Dead Horses | 3:37 | |
| The Eye | Brandi Carlile | 3:31 | |
| I'll Be Here in the Morning | 10 String Symphony | 4:34 | |
| Lord Won't You Help Me | Sara Watkins | 2:57 | |
| Working Man | Maya De Vitry | 3:22 | |
| Table For One | Courtney Marie Andrews | 3:59 | |
| Only Lonely | The Ballroom Thieves | 3:37 | |
| To The Wild | The Steel Wheels | 4:13 | |
| Be My Husband | I'm With Her, Sara Watkins, Sarah Jarosz, Aoife O'Donovan | 3:15 | |
| Little Birdie (feat. Sarah Jarosz) | Traditional, Silkroad Ensemble, Yo-Yo Ma, Sarah Jarosz | 2:48 | |
| You Can Close Your Eyes | The Brother Brothers, Sarah Jarosz | 3:04 | |
| Stitch In Time | Pharis & Jason Romero | 3:51 | |
| Wildflower Honey | The Stray Birds | 4:08 | |
| Young In All The Wrong Ways | Sara Watkins | 4:18 | |
| Stanley Park | Aoife O'Donovan | 2:50 | |
| Neighborhood Name | Watkins Family Hour | 3:26 | |
| Dream in Blue | The Stray Birds | 3:32 | |
| Hands on a Grain of Sand | Amelia Curran | 3:48 | |
| Strong Enough | Molly Tuttle, Madison Cunningham | 3:17 | |
| A Wanderer I'll Stay | Pharis & Jason Romero | 3:37 | |
| Wild Bill Jones | Nate Leath, Sarah Jarosz, Mark Schatz, Danny Knicely | 2:55 | |
| Send My Love (To Your New Lover) - Live | I'm With Her, Paul Kowert | 3:45 | |
| Yours To Bear | honeyhoney | 4:37 | |
| Milk And Honey | Ondara, Madison Cunningham | 2:54 | |
| Lighthouse | Caroline Spence, Sarah Jarosz | 3:31 | |
| American Flowers | Birds of Chicago | 6:10 | |
| Peace | William G Tee, Dillistone, Sarah Jarosz | 2:44 | |