Portland is located at the north-eastern tip of the island. It is to the north of St. Thomas and to the east of St. Mary. The parish was named after the Duke of Portland who was Governor of Jamaica in 1723. It extends from the sea coast to the highest peak of the Blue Mountains and is noted for its fertility and the beauty of its scenery. It also experiences a significant amount of rainfall annually. The town of Port Antonio, which is also the parish capital, is located on the northern coast, approximately in the centre of the Parish perimeter. It is a combination of the original parish of St. George with a part of eastern St. Thomas and a part of St. Mary. During that same year a grant of thirty acres of land was offered by the Governor to every white Protestant wishing to settle in Portland. To every free mulatto, Indian, or Negro, was offered a grant of twenty acres, all in an attempt to populate the parish. The response to the offer was so poor, that the Governor increased his incentives to include provisions of beef and flour and an offer to free the inhabitants from taxes and arrest for three years. However, all these efforts came to naught as the prospective immigrants were unable to withstand the rigors of cultivating on the mountainsides and the challenges of the Maroons who lived in the intimidating Blue and John Crow Mountains. After a series of battles with the Maroons during the 1730s, the British captured Nanny Town, the settlement governed by the woman who was later to become Jamaica’s first National Heroine: Nanny.

Eventually many prosperous sugar plantations were developed near the coast. The parish experienced a later period of prosperity during the banana boom, which also contributed to the development of the capital of Port Antonio as one of Jamaica’s first tourist resorts with one of the island’s popular attractions, rafting on the Rio Grande and the annual Blue Marlin fishing tournament.

The parish is a richly blessed piece of land with very fertile soil, wonderful green mountains and exquisite beaches. The Blue mountain range, with the highest peak in Jamaica at 2256 meters, comes within the boundaries of Portland. These mountains had provided safe haven for many an escaped slave when slavery was still practiced. The mountains also ensure that the parish receives the highest rainfall in the island from the northeast trade winds. Port Antonio also has two harbors. Portland has as many as 17 rivers watering the whole parish largest of which are the Rio Grande, Buff Bay and Hectors Rivers. The entire Portland coastline has several land formations like caves, bays, waterfalls and hills. It is no wonder that this beautiful land is a tourist’s paradise.

Hectors Rivers. The entire Portland coastline has several land formations like caves, bays, waterfalls and hills. It is no wonder that this beautiful land is a tourist’s paradise. Major History Features FOLLY – the Legend
The legend states that a young American decided to build a summer house for his bride. The house was built on land at the eastern headland of Port Antonio harbour, with a commanding view of the sea. Legend also states that the completed house was white, the flowers which adorned the gardens were white, so too were doves, monkeys and peacocks which the bridegroom kept in the gardens. As soon as the young bride set foot in the completed house, to her dismay, a wall crumbled. In building the house, sea sand was used in the cement mixture. Distressed, she fled the scene vowing never to return. Her distraught husband pined away and soon died. His remains, at his request, were put at a point where the sea water would splash upon the grave. The facts are that although the house wasn’t correctly built, it survived longer than the legend would make one think. Also, the bride was not young, in fact, when she came to Folly in 1905, she was already a grandmother. What is more, her husband died in 1912 and photographs taken as late as 1914, show that she continued to live at Folly long after his death.

Moore Town:
This Maroon village on the banks of the Wild Cane River was founded in 1739 when the Maroons signed a peace treaty with the English and obtained their freedom and 500 acres of land. The treaty forbad them to harbour runaway slaves. The community is still governed by a Colonel assisted by a Council of 24 members. At one end of the village is Bump Grave. It is the grave of the Right Excellent Nanny of the Maroons, Jamaica's only National Heroine. The plaque on the grave reads: "Nanny of the Maroons/ National Hero of Jamaica/Beneath this place known as Bump Grave lies the body of Nanny, indomitable and skilled Chieftains of the Windward Maroons who founded this town." Both the Jamaican and Maroon flags fly there.
Nanny Town
This Maroon settlement referred to as "the great negro town" in most official documents is situated on the southern slopes of the Blue Mountains in the Stony River Valley. .A recent expedition discovered the long buried remains of this town. Its inhabitants were the Windward Maroons of Queen Nanny and Captain Quaco who as an excellent guerilla fighter. They successfully terrorized the plantocracy in that end of the island. The town was captured in 1734 by a successful expedition of white forces, prior to the signing of the June 1739 Peace Treaty.