By the mid-19th century, the sugar economy that had defined Portland’s colonial role was in terminal decline. The very conditions that had once hindered traditional agriculture—the parish’s relentless rainfall and the steep, humid valleys—were the exact requirements for a new, delicate export. The transition to the modern era was marked in 1870 by the arrival of an 85-ton schooner named the Telegraph, which signaled a pivot from local subsistence toward a global commodity market.
Captain Lorenzo Dow Baker, an American merchant mariner, sailed into the harbor and recognized a market where others saw only a local staple. He purchased 1,450 bunches of bananas at a modest local price, reselling them in the United States for a profit that effectively signaled the end of Portland's agricultural isolation. This single merchant venture catalyzed a development engine that would fundamentally reshape the social and physical landscape of the entire parish.
In 1885, Baker partnered with Andrew W. Preston to form the Boston Fruit Company. This move shifted the industry toward vertical integration—a system designed to control the land, the shipping, and the marketing of the fruit under a single administrative umbrella.
This organizational model eventually evolved into the United Fruit Company, an entity that effectively governed the rhythm of Port Antonio. The "Green Gold" of the banana required a precise logistical schedule; the fruit was perishable and required rapid transport. To meet this demand, the corporate structure built a permanent physical frame in the parish, from specialized wharves to the first significant inland transport networks.
The expansion of the banana estates significantly altered the social geography of Portland. As the corporate giants acquired the fertile valley floors, many independent Afro-Jamaican farmers—who had been instrumental in the early years of the trade—found themselves pushed to the more rugged, higher elevations. This "shifting geography" forced a choice between laboring on the large estates or maintaining an increasingly isolated independence in the hills.
The prosperity of the "Golden Age" rested upon a foundation of manual labor that was as rhythmic as it was grueling. Archival records preserve the memory of the banana carriers—often women—who moved in tandem to load the fruit onto the steamers. This labor was the kinetic force that connected the rural interior to the global markets of the north.
The wealth generated by the banana trade did not just leave the harbor; it was anchored in the town's expanding infrastructure. The capital from the fruit financed the permanent masonry of the courthouse, the navigational reach of the Folly Point Lighthouse, and the early rail lines that connected the interior to the coast.