| Train Song | Watchhouse | 2:02 | |
| Texas Moon | Vincent Neil Emerson | 3:25 | |
| Waterloo | The Tumbleweeds | 2:28 | |
| Walking | Chris Acker | 4:48 | |
| I Must Be Somebody Else You've Known | The International Submarine Band | 2:20 | |
| Mother Earth | Willie Watson | 3:36 | |
| Trading Paint | The Texas Gentlemen | 3:09 | |
| I Love Leaving | Jonny Fritz | 3:26 | |
| Orion's Gut | Chris Acker | 3:12 | |
| I Ride Junk | Nick Hans | 3:41 | |
| Goodbye My Son | The Good Luck Thrift Store Outfit | 3:25 | |
| Hard On You | Daniel Romano | 3:27 | |
| Freight Train | Cat Clyde, Jeremie Albino | 2:05 | |
| Verde River | Kassi Valazza | 4:24 | |
| Mahogany | Chris Acker | 3:21 | |
| Quite a Feelin' | Barna Howard | 4:09 | |
| The Outskirts | Trampled by Turtles | 5:53 | |
| Fifteen Passenger Van | Jonny Fritz | 2:05 | |
| Same Blood as Mine | The Deslondes, Riley Downing, Sam Doores | 3:28 | |
| You're Dreaming | The Cactus Blossoms | 3:25 | |
| Perfect Timing | Drive-By Truckers | 2:57 | |
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| She Lies Alone | The Tumbleweeds | 2:48 | |
| Leaf Change | Willy Tea Taylor, The River Arkansas | 3:52 | |
| Cigarette Machine | Fred Eaglesmith | 4:31 | |
| What Are They Doing In Heaven Today? | The Deslondes, Sam Doores, Twain | 3:00 | |
| Hound Dog | Rattlesnake Milk | 4:01 | |
| Broken | John Craigie | 2:54 | |
| Jailhouse Lament | Cole Wilson, The Tumbleweeds | 2:45 | |
| Mama Bake a Pie (Daddy Kill a Chicken) | Drive-By Truckers | 3:19 | |
| Playing the Fool | The Lostines | 2:25 | |
| Canyon | Emily Nenni | 3:02 | |
| Take Me in the Lifeboat | Ken Lemon, The Tumbleweeds | 2:40 | |
| Run Wild | Twain, The Deslondes | 2:56 | |
| Rise and Fall | Nick Hans | 3:54 | |
| You're the Reason I'm Living | Cole Wilson, The Tumbleweeds | 3:19 | |
| Long John Dean | Willie Watson | 2:54 | |
| Faded Loves & Memories | Kentucky John Clay, John R. Miller, Chloe Edmonstone | 3:18 | |
| Lot Lizard | Joshua Ray Walker | 4:18 | |
| Home Again | The Deslondes, Riley Downing | 2:44 | |
| Maybelline | Ramsay Midwood | 3:17 | |
| Sweethearts or Strangers | The Tumbleweeds | 3:02 | |
| Highway Shine | Vincent Neil Emerson | 3:33 | |
| I Wish We Had Our Time Again | Todd Snider | 2:28 | |
| Miss'ippi | Nick Shoulders | 3:23 | |
| Blossoms in the Springtime | Cole Wilson, The Tumbleweeds | 2:40 | |
| Jump Down Baby | Esther Rose | 3:14 | |
| Where Ya Been? | Luke Bell | 3:29 | |
| Got to Me Since | Izaak Opatz | 3:43 | |
| Alligator's Lament | Ramsay Midwood | 2:55 | |
