Montego Bay is a relatively young town, without the historical importance of its neighbour Falmouth in Trelawny and Lucea in Hanover. The St. James town took off as a community with the rapid growth of tourism in western Jamaica. However, the area of Montego Bay goes back a long way, when the Taino Indians (incorrectly called Arawak Indians) had a large village in Fairfield which was one of the top 14 caciquecoms in the island. Fairfield was chosen for its closeness to the Montego River along which cottonwood canoes could be paddled out into the Bogue Islands for fishing. Their religious ceremonies took place in caves, one at Williamsfield, near John's Hall and another at Crawle west of Rosehall.
Christopher Columbus was probably Montego Bay's first 'tourist' when he sailed into the bay on May 9, 1494. It is from Montego Bay that that a Taino Indian joined the crew of Columbus and became the first indigenous inhabitant of the Americans to visit Europe. Columbus touched at Montego Bay once more three months later on his way from Cape Cruz in Cuba, before completing his exploration of Jamaica. Columbus called the bay El Gulfo de Bien Tiempo, which is the Golf of Fair Weather, but Spanish colonists later called it the less complicated name of Manteca Bahia, which is Lard Bay. The town's start however, was more, ignominious- as the lard capital of the Caribbean. "Montego" derives from the Spanish word for hog fat, Manteca. Wild boars in the hills provided the lard. Later, about 1511, they started sugar farms and used Tainos as slaves to look for the elusive gold mines. Montego Bay then became a major port for bananas and sugar.
The Spaniards erected a tower in flankers and there was a monastery at Miranda Hill and dwellings in Mango walk.
In 1655, the British invaded Jamaica and won it from the Spanish after a brief squirmish. Then began the division of the land, and some large plots of land were awarded to victorious soldiers. Each lot or parent was about 100 acres and were given to such officers as Colonel Jonathan Barnett, who owned these cane fields that now house the City of Montego Bay and after whom Barnett Estate was named died and was buried near the Holy Trinity Church near Westgate, the Lawrences and Richard and Mary Rutledge of True Friendship, which was renamed Rose Hall and was passed down to the notorious Annie Palmer.
In 1673, while the population of Jamaica was 17,268, St. James had a mere population 146. St. James was to remain a poor parish until the middle of the 18th century. The 'Northsiders' as they were called used their slaves to clear the land and tried to grow indigo, a small legume which produced a purple dye which was used as an ink. Sugar however, soon proved to be more profitable. The parish of St. James was formed in 1671 apparently named after the brother of King Charles ??, the Duke of York. The parish was considerably larger than now because in 1770 more than half of it was cut off to form the parish of Trelawny. One of the reasons for the slow development of the 'Northside' had to do with the numerous of attacks from the Buccaneers and later the Maroons.
Montego Bay slowly grew in importance, as its trade expanded from small beginnings. By 1791, over 150 ships were using the harbour each year, as ships came from Africa with slaves, from Charleston and Wilmington in the United States, and Greenock and Belfast in Britain. Montego Bay also played a pivotal role in the outbreak of the Second Maroon War in 1795, when two Maroons who were caught pig-stealing were flogged in the western town. This war had more of a dishonourable end as General Balcarres dishonoured the pledge of General Walpole not to deport the Maroons, and he sent 600 of them to Nova Scotia. The Montego Bay planters no longer had to worry about the threat of the Maroons. A new courthouse was completed in 1804, and it was there that Sam Sharpe and his fellow 'rebels' were tried and marched outside to be hung.

Remains of the Old Fort.