1790
1791
On the 18th of August, 1790, the regiment embarked from Ireland for Nova Scotia, and in 1791 it was removed to the island of Jamaica, where it remained five years.
1793
1794
A revolution broke out in France, and the republican principles which filled that kingdom with anarchy, confusion, and bloodshed, soon extended to the French West India Settlements, where the blacks and mulattoes rose in arms against the European planters, and filled the islands with rapine and devastation. Many of the respectable inhabitants of the French island of St. Domingo solicited the protection of the British government against the fury of the blacks, and a detachment of British troops proceeded to their aid, from Jamaica, in 1793. The SIXTEENTH regiment furnished a portion of this detachment, but the climate of St. Domingo proved injurious to the health of the British troops, and the whole of the party of the SIXTEENTH died of a pestilential fever, excepting Lieutenant Vernon and one serjeant, who rejoined the regiment at Jamaica.
1795
The island of Jamaica was taken from the Spaniards, by an English armament in 1655 (during the commonwealth under Cromwell), when the slaves belonging to the Spanish planters fled to the mountains, where they lived in savage independence, and were called "Maroons." They procured arms, became expert marksmen, and frequently committed outrages against the British inhabitants. In 1738 a treaty was concluded with them, and they received a grant of land; but the pernicious doctrines of the French republicans were circulated among the Maroons, who were joined by a number of runaway slaves, and commenced hostilities against the English in 1795. The SIXTEENTH served in the Maroon war, when the soldiers encountered many difficulties, and at first sustained some reverses, from the difficult nature of the mountainous districts into which they had to penetrate, and from the expert character of the Maroon warriors in bush-fighting among rocks and dells covered with trees and underwood. A detachment of the SIXTEENTH was first called into action; and in October the regiment, commanded by Major John Skinner, who held the local rank of Colonel, was called into the field. This officer had served many years in the regiment; he had distinguished himself in the American war, while serving with Tarleton's Legion, with which corps he was present at numerous engagements, and on joining the field force in the Maroon war, his presence inspired the troops with confidence. Offensive operations were conducted with prudence and skill, and by a strict combination in the movements of the troops employed, united with valour and discipline, the Maroons were driven from their mountain-fastnesses, and chased from post to post, until they were forced to submit. In performing this service, the soldiers underwent great fatigue and privation, and they conquered the Maroons in a part of the island where no European had ever before thought of penetrating. Captain Drummond, of the SIXTEENTH, distinguished himself in this war.
1796
The Maroons tendered their submission in March, 1796, and they were afterwards removed from the island.
1797
Having become considerably reduced in numbers, the regiment returned to England, towards the close of this year, and was stationed a short time at Greenwich, from whence it embarked for Scotland, early in 1797; at the same time it was ordered to recruit with boys.