The history of Oracabessa dates back over 500 years to the year 1502 when Christopher Columbus sailed into Oracabessa Bay, and bestowed the name Santa Maria island on the small island located in what is now Goldeneye estate. At the time, the area was sparsely populated by Taino and Arawak Indians and the Spanish established a small supply post named Oracabeza. It remained a Spanish settlement until 1655, when the British captured the North Coast of the island.
For the next 200 years, Oracabessa functioned as a tiny agricultural community with its main crop, bananas, controlled by a small group of British landowners. The arrival of Reverend James Phillippo in 1834 changed the course of Oracabessa's history. Phillippo built the first church in Oracabessa and led a defiant protest against the local landowner's refusal to sell land to former slaves. The parish of St. Mary, where Oracabessa is located, had a large population of freedom fighters, known as Jamaican Maroons, who worked closely with Phillippo in his quest for justice. With this show of force, combined with a decree from the British Government, the landowner's relented and sold Phillippo enough land to build houses, schools, churches and businesses for the hundreds of residents in the area.
Reverend Phillippo was a pioneer of Free Villages, which were settlements that functioned largely without influence from the colonial government. As part of this unique social experiment, Phillippo purchased land from plantation owners and resold the land to the former slaves with terms that required them to only repay what they could afford. Within 3 years, he had received full payment and the residents of Oracabessa owned their land and businesses outright. Phillippo's belief and faith in the people of Oracabessa led to the development of other Free Villages throughout the island.
Phillippo successfully demonstrated that the Free Village concept worked and that it represented a great opportunity
