Chapter 2 examines the transformative effect of the opening of Highway 1 in 1937. This chapter argues that planning foresight positioned Big Sur to become one of the state’s best-preserved coastlines, while popular representations of its dramatic natural elements provided the justification for such preservation. Before the highway opened, Monterey County established some of the first ordinances in the nation to prohibit billboards and require well-designed construction along the highway. Tourists responded with enthusiasm, drawn by Jeffers’s powerful verse and countless national newspaper stories extoling Big Sur’s beauty. In 1944 the avant-garde writer Henry Miller settled in Big Sur. Like Jeffers’s work, Miller’s representation of Big Sur left the impression that people belonged in and to this landscape. The highway set Big Sur on an irrevocable course toward participation in contemporary society, but aesthetic zoning, praise from the national media, and accounts from residents like Miller, all worked to blur the modern aspects of this coastal destination. Visitors to Big Sur sought a glimpse of the frontier that had supposedly closed four decades earlier, but ironically, the frontier they encountered derived at least in part from government regulations that responded to California’s phenomenal growth.