Cudjoe's Town was located in the mountains in the southern extremities of the parish of St James, close to the border of Westmoreland, Jamaica.

[1] In 1690, a large number of Akan freedom fighters already living in the mountains launched an assault on the Sutton's Estate in Clarendon, central Jamaica, free between 300 and 400 enslaved people.

[9] Leeward Maroons from Trelawny Town helped the colonial authorities to put down the rebellions of Tacky and Apongo between 1760-6, and were financially rewarded for their assistance.

[15] However, the Maroons of Trelawny Town were unable to maintain their guerrilla campaign during the drought months, and Colonel George Walpole employed a scorched-earth policy, backed up by the importation of hunting dogs.

By 22 December Walpole was able to persuade Montague James and his Maroon lieutenants, including Major Jarrett, Charles Samuels and Andrew Smith, to come to terms.

[16][17] Walpole promised the Maroons that they would not be transported off the island if they laid down their arms, and the Trelawny Town warriors agreed to submit to terms.

The Second Maroon War proved costly to the colonial authorities, and in an attempt to recoup their losses, the Jamaica Assembly auctioned off most of the 1,500 acres belonging to Trelawny Town.

In 1800, the British government eventually agreed to transport the Trelawny Maroons to Sierra Leone, where they helped to suppress a rebellion by the Black Nova Scotians.

The Trelawny Maroons flourished in Sierra Leone at first, but their situation soon soured, and they submitted petitions to British government, asking for permission to return to Jamaica.

Mary Brown and her family, which included her daughter Sarah McGale and a Spanish son-in-law, sold off their property in Sierra Leone, bought a schooner, and set sail for Jamaica.

[25] Brown, Ricketts and their families petitioned the Jamaican Assembly, pointing out they had used up all their resources in returning to their homeland, and requested financial assistance in purchasing the property of their ancestors.

However, their request was ignored by the Jamaican Assembly, so Brown, Ricketts and their families settled on land near Maroon Town, contributing to the establishment of the village of Flagstaff.

However, Returned Maroon oral historians describe how many of their ancestors landed at Lucea, Jamaica, working on the canefields of Westmoreland Parish, as well as Hampden and Long Pond in Trelawny, before eventually settling in Flagstaff.