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Episode 416 first aired on March 16, 2016
| Artist | Song |
|---|---|
| Old Settlers Music Fest | Humming House – Fly On |
| Hayes Carll | Chances Are |
| Jitterbug Vipers | Viper Just The Same |
| Band Of Heathens | Shine A Light |
| The Sound Of Austin | Good Day For The Blues |
| Rodney Crowell | Moving Work Of Art |
| Carolyn Wonderland | What Good Can Drinkin’ Do |
| Bob Schneider | Honeypot |
| Sarah Jarosz | Song Up In Her Head |
| Milkdrive | Soho |
| The Deer | Do Return |
| The Suffers | Make Some Room |
| Old Settlers Music Fest Promo | The Infamous Stringdusters – Light & Love |
| Wood & Wire – Overblown |