In 1739 the Maroons signed a peace treaty with the British and this led to a new period of development in Portland. Settlers started pouring in, accepting the Governor's offer of free land and slaves. Many began large scale sugar cultivation. By 1779 there were 38 large.
Baker established an office in Port Antonio and began to make an average
of 5 trips a year and eventually, in 1881, moved his wife and 4 children
to Jamaica. He and his family spent most of the year in Jamaica and lived
in Wellfleet during the summer and early fall.
He formed the Boston Fruit Company by buying out smaller concerns. Small farmers began to buy and rent land all over the parish to plant banana. His company, through many mergers and acquisitions, made possible the giant conglomerate Chiquita brands.
Baker expanded by buying estates (including Bog, near Port Antonio and Bowden in Port Morant), more ships and building piers. He soon faced increased competition, especially from the Keith and Lindo families who were engaged in a thriving fruit trade from Costa Rica to New York. In 1885, after buying out some of his competitors (including the Keith interests) his enterprise became known as the United Fruit Company. By 1902 Baker controlled the entire island's banana trade (St. Mary had also emerged as a major producer of bananas) and he went on to supply fruit all along the east coast of the United States and later, New Orleans, Montreal and London. Regular exports to Britain had begun in 1901 with Sir Alfred Jones's Imperial Direct Steam Line (which included refrigerated machinery) employed to the United Fruit Company and later bought out by them. Some 650 tonnes of banana were shipped to the UK each month.
As Baker's trade grew, Port Antonio became the second most important town in Jamaica. Most of his workers lived in Portland. Those who did not grow bananas, reaped them or loaded them onto ships, earning some 70 cents per day. Money was new to the people of Portland and it is said that some became so rich that they used five-pound notes to light their cigarettes. Knowledge of saving was sadly lacking.
In addition to the Titchfield which was only open during the winter season, Baker also owned a hotel back home in Wellfleet called the Chequessett which was only open during the summer season. Baker often used the same staff in both locations, thus providing year around employment for many persons both in Jamaica and Wellfleet.
In 1905 the Titchfield hotel boasted 600 feet of piazza and 400 rooms. It was said that "no other hotel this side of the Atlantic provided as many conveniences that minister to the pleasure of travellers as the Titchfield." It became known for its afternoon tea on the piazza and bathing in bath houses.
another of Titchfield Hotel's great claims to fame is that it was once owned by famous Hollywood swashbuckler Errol Flynn who died before he could execute on any of his plans to develop the hotel. In the late 1960s the hotel was destroyed by fire and today only the ruins of this great landmark still stand.