Beginning with several aesthetic aerial shots of mountainous highways, Winding Road is a short film about Todd, the leader of a traveling rock band and Brandiss, the self assured bartender. When Todd’s band tour schedule brings the group to the bar that Brandiss works at and the two are reunited after some time apart, Les, a regular customer tries to convince Brandiss to step outside of her comfort zone and accept how she feels about the nomadic band leader. We see Brandiss as an extremely level-headed person since she works at a bar, and handles more personal questions, mainly about how she came to lose her arm, with charm and wit. It seems everyone is aware of the tension between Brandiss and Todd, though both of them continue with their attempts to cover it. As the band leaves, Todd leaves Brandiss a note telling her that he loves her and will be back next year.