The Maroon communities of Jamaica trace their origins to people formerly enslaved by the Spanish who refused to submit when the British seized the island in 1655. Over the following decades, more enslaved people fled the sugar plantations and joined these autonomous communities in the mountains. Among them, according to tradition, was a woman born in what is now Ghana, a member of the Ashanti nation and part of the Akan people. She arrived in Jamaica in chains. She left the plantations with five companions known as her 'brothers-in-arms': Cudjoe, Accompong, Johnny, Cuffy, and Quao. Together, they would scatter across the island to organize resistance. Cudjoe became the leader of the Leeward Maroons in the west. Nanny and Quao made their way to Portland Parish and the Blue Mountains, where they would build something the British could not easily destroy.

By 1720, Nanny and Quao had organized the Windward Maroons into a settlement perched on a 900-foot ridge overlooking the Stony River. The position was nearly impregnable. Any approaching force had to climb through thick mountain jungle under observation from lookouts stationed along the route. Warriors could be summoned instantly by the blast of the abeng. The community was organized along the lines of an Ashanti village, with Nanny serving as both military strategist and spiritual leader, drawing on a deep knowledge of herbal medicine and the traditions of her people. The Maroons sent traders to coastal towns to exchange food for weapons and cloth. When trading failed, they raided plantations directly, taking what they needed and liberating enslaved people who joined the settlement.

The colonial government launched the First Maroon War in the 1730s, determined to crush the communities that were bleeding the plantation economy through raids and by offering a destination for those who escaped bondage. Nanny Town bore the brunt of the British assault in the east. Between 1728 and 1734, colonial forces attacked repeatedly. The Maroons fought with a tactical ingenuity that British soldiers, trained for European-style warfare, could not counter. In the mountain rainforest, Maroon fighters disguised themselves as bushes and trees, blending into the landscape until the enemy walked into point-blank range. Uncamouflaged Maroons would show themselves deliberately, drawing the British forward into prepared ambush zones where hidden fighters waited. The British captured Nanny Town multiple times, yet each occupation proved temporary. The Maroons melted into the mountains and returned to reclaim their home.

Nanny's legacy extends beyond military resistance. Over the span of approximately fifty years, she is credited with freeing more than 800 enslaved people, guiding them from the plantations to the Maroon settlements. After the war, a deed from the colonial government granted Nanny more than 500 acres of land where the Maroons could live, raise animals, and grow crops. It was a grudging acknowledgment that the British had failed to defeat them by force and had to negotiate instead. The Maroons of Nanny Town also claim descent from both escaped African people and Taino men and women, the island's indigenous inhabitants, a lineage that roots the community in Jamaica itself, not just in resistance to European power.

In 1740, Quao, another Windward Maroon leader, signed a peace treaty with the British. The agreement split the community. Quao's supporters relocated to what became Crawford's Town. The Maroons of Nanny Town moved to Moore Town, in the Rio Grande valley, where their descendants live today. Nanny herself is now a National Hero of Jamaica, one of only seven in the country's history, and the only woman among them. Her portrait appears on the Jamaican $500 bill. The site of Nanny Town in the Blue Mountains remains largely as the jungle reclaimed it: a ridge above a river, steep enough to exhaust anyone climbing toward it, quiet enough now to hear only birdsong where the abeng once sounded.