Titchfield High School is a secondary high school in Port Antonio, Jamaica, in the northern part of Portland. The school was established in January 1786 and is the fifth-oldest high school in the country.In 1870 a settlement, in Port Antonio, was established for the general use of all the people in the area. By 1875 these 350 acres of land was being unlawfully used and was in danger of being lost. It was then given over to some trustees later known as the "Titchfield Trust" to raise funds for erecting a free school to be maintained and endowed from the proceeds of the land.The school was to provide instruction for the youth without charge to their parents, in the three basic skills – Reading, Writing and Arithmetic and also Latin and Greek. Teachers were to be of the Church of England and the school would be open to children of the island in general, although preference was to be given to those from the area.The school began in 1786 in an area in Port Antonio known as "Free School" and, in 1883, the management of the Trust was given to the Jamaica School Commission. It leased, from theGovernment, the old military barracks of Fort George for the siting of the school. A day school for boys and one for girls was established in 1886 with Major W. H. Plant as headmaster.At first, the school consisted of Infant, Elementary and Secondary Departments but later, the Elementary and Infant departments were separated from the Trust and Titchfield School was then the only Secondary School.