The country-folk songsmith will release his debut record under Big Loud on September 22.
The bittersweet set of visuals tell the story of a young man who's been diagnosed with a terminal illness.
The sampler EP includes the previously teased ‘All Again’, ‘West of Lonesome’, ‘Cue Country Roads’ and ‘Family Ties’.
The newly unveiled string of shows will take the country-pop megastar across Florida, Louisiana, Indiana and Ontario.
Taken from his forthcoming Shooter Jennings album, Golden State
The winner will receive a Taylor 214ce guitar and coverage across Holler's site and socials.