The geography explains everything. The Cockpit Country is a landscape of conical limestone hills and deep sinkholes stretching across parts of Saint James, Saint Elizabeth, and Trelawny parishes. Dense tropical vegetation fills the hollows between the hills, and the terrain is so rugged that it functioned as a natural fortress for people who knew its contours. Enslaved people who escaped from the coastal plantations fled into this interior, where pursuit was nearly impossible. They became the Jamaican Maroons, communities of free people living beyond the reach of colonial control. Today the area still supports small-scale farming, with bananas serving as the primary cash crop. Ground provisions including yam remain staples, and the Maroon Pride Banana Chips brand traces its origins to this community.

In the 1730s, a leader named Cudjoe organized the Maroons of western Jamaica into a fighting force that used the Cockpit Country's terrain to devastating effect against British soldiers. The First Maroon War ground on until Governor Edward Trelawny authorized the signing of a treaty with Cudjoe in 1739. Under its terms, the Maroons won their freedom and the right to self-governance in exchange for returning future runaway enslaved people, a compromise that reveals both the strength of the Maroons' military position and the moral contradictions embedded in their hard-won autonomy. Cudjoe's Town became Trelawny Town, bearing the governor's name as if the treaty had made it a British creation rather than a Maroon stronghold.

Peace held for over fifty years before the Second Maroon War erupted in 1795. This time, the outcome was different. After the conflict ended in 1796, the colonial authorities deported the Trelawny Town Maroons, first to Nova Scotia's harsh winters and then to Sierra Leone in West Africa. It was an extraordinary forced migration: people who had won their freedom in the Caribbean tropics were shipped to the cold of Atlantic Canada and eventually to a continent their ancestors had been taken from generations earlier. The British renamed their emptied settlement Maroon Town and stationed troops there. For half a century, the site served as a military barracks, though officers consistently complained about the dampness and frequent rainfall. A hurricane destroyed most of the barracks buildings in 1812, and the colonial government eventually abandoned the outpost in the 1850s.

The story did not end with deportation. When slavery was abolished in Jamaica in the 1830s, scores of Trelawny Maroons made the journey back across the Atlantic, drawn to the land their parents and grandparents had fought for. Many settled not in Maroon Town itself but in the nearby village of Flagstaff. As late as 1905, visitors observed Returned Maroons from Flagstaff hunting wild hogs in the surrounding hills, practicing a way of life that connected them to the Maroon traditions their families had carried through exile. Today Maroon Town has a population of roughly 3,100 and continues to be a site of archaeological research, its soil still yielding evidence of the people who lived, fought, and were scattered from this place.