While places like Holbrook faded, others adapted and even thrived. Amarillo, Texas, exemplifies this resilience, with Cadillac Ranch as an example of the town’s creative reinvention. Established in 1974, this quirky landmark features a row of half-buried, graffiti-covered Cadillacs that attract over a million visitors annually. It has become a lasting emblem of Amarillo’s ability to blend historic roots with modern artistic expression. The continued popularity of Cadillac Ranch and other local attractions has helped Amarillo maintain a thriving economy and cement its status as an iconic roadside destination.

While this historic highway stands as a testament to change and adaptation, my trip through the American South revealed an area still grappling with the legacies of a bygone era. Its identity has been molded, in part, by agrarian roots, particularly the rise of plantation culture, and by the lasting impact of the Civil War. The region’s pride in its traditions contrasts sharply with the lingering wounds from those tumultuous times. These scars continue to influence the present in ways both visible and profound.

Wormsloe State Historic Site, where Bruno and I found respite under a grove of moss-draped oaks, vividly illustrates the South’s complicated past. Founded in the eighteenth century, it evolved from a fortified colonial estate into a thriving plantation. Like so many institutions during the Antebellum era, it relied on the brutal exploitation of enslaved African men, women, and children. As visitors approach the grand entrance, unique to this region, they are greeted by a landscape of striking natural beauty that conceals a legacy of human suffering.