For the past two decades, the cowboy who inhabits country music narratives has appeared with increasing frequency in a seaside setting or beach environment that appears to contradict the well-established conventions of place and space in the genre. Where rural farms and ranches, for instance, evoked codes of white, male working-class sustenance, physical labor, and pride in forging a symbiotic relationship with the land, the new beach imagery offered a different catalog of associative meaning: leisure, escape, travel away from one’s home and roots, and a sense of unbounded freedom. This chapter traces the rise of beach imagery as a setting and reference point in country music, both in song narratives and music videos, since the 1990s. Ultimately, this chapter suggests that, in spite of their ubiquity, these beach settings are only comprehensible to their audience because the underlying cultural meaning of country music has fundamentally changed.