Flagstaff is named for (duhh!) the flagstaff that was erected there around the time of the The Second Maroon War which started in July 1795
Prior to the war, the town was called Cudjoe/Kojo Town (by the Maroons) and Trelawny Town by the British.
The origin of the English name "Trelawny Town" was with Governor Edward Trelawny (1738-52) who was responsible for signing the Maroon Treaty with Cudjoe/Kojo in 1738. The town is shown on at least one map from the period as "Trelawny Negro Town" and it was located in the original Parish of St James.
By 1771, St James had been divided into two, with the eastern end being called Trelawny Parish, in honour of the presiding Governor, William Trelawny (1767-71). It so happens that "Trelawny Negro Town" remained in St James parish, only a mile or so from the Trelawny border. One can well imagine that the British were pleased to clear up this confusion by changing the name after the War.
Barracks were built in the upper part of Trelawny Town,and the military graveyard can still be seen. The lower part of the Town was
originally called "Furry's Town"and corresponds to the
present-day Maroon Town.
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