The first civilian settler in the Troy valley was Mr Knowles, around 1800, and his house, "Troy", is still standing near the road junction to Craighead. Troy was the site of a military fort, the "Troy Post", established in 1796 by Col. Robertson and Major Shaw under General Walpole. This was located at the junction to the Windsor trail and was used by the Clarendon and Vere Militia and housed the canine division with wolfhounds "big as colts" which were imported from Cuba during the Second Maroon War! It should be noted that this area of the country was very undeveloped in the 18th century and was virtually unexplored except by the Maroons.

In 1840 the Jamaica Almanac reports that Troy consisted of 2600 acres and belonged to William Carter,