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Trelawny was established in 1770 from parts of Saint James and Saint Ann and was named for the Governor of Jamaica at the time, Sir William Trelawny, who died in Jamaica in 1772. The first capital was Martha Brae. The parish covers about 338 square miles, making it the fifth largest on the island. Trelawny has a population of 74,000. Some of the major towns in the parish are Clarks Town, Stewart Town, Duncans, Wakefield, Jackson Town, Ulster Spring, Wait-a-Bit and Albert Town.

Much of Trelawny is flat with wide plains such as Queen of Spain’s Valley and Windsor. The southern section of the parish is part of the Cockpit Country and is uninhabitable. This makes is a natural reserve for plants and animal life. Most of Jamaica’s 27 bird species are found there and sometimes the giant swallowtail butterfly, the largest butterfly in the western hemisphere. Covered in limestone, there are cockpits, sinkholes, caves and underground passages. Windsor Cave is one of the largest and the roar of the Martha Brae River can be heard there during rainy season as it flows underground. Carnabi Cave is known for its phosphate deposits. There are caves near Pantrepant where Arawak/Taino wall carvings can be found. The main rivers in Trelawny are the Martha Brae, Rio Bueno, Cane and Quashie.

Trelawny is best known for its sugar plantations and sugar factories. It allegedly had more sugar plantations than any other parish so they needed a seacoast town to export sugar. Lands were bought from Edward Moulton Barrett (the father of the poetess Elizabeth Barrett Browning) and Barrett Town became one of the best laid out towns in Jamaica. It was renamed Falmouth and the planters erected luxurious townhouses. Falmouth became a thriving seaport and social center and is a historic and architectural treasure.

The largest group of Maroons, descendants of the slaves left in the island by the Spaniards, lived in the southern section of the parish in the Cockpit Country. Their chief town was Trelawny Town. A treaty between the Maroons and the English in 1739 gave the Maroons their freedom and land and effectively stopped their raids on the plantations. In 1795 the second Maroon uprising led to over 600 Maroons being exiled to Nova Scotia in Canada and later to Sierra Leone in Africa in 1800. Trelawny Town was destroyed in retaliation.