The fort was built by the British Royal Engineers in 1794 at an elevation of approximately 947 feet over Road Town, and was erected on top of an earlier wooden stockade believed to have been originally built by the privateer Joost van Dyk to act as a lookout post.
Road Town became the Territory's capital instead of much better anchorages at Soper's Hole, Hodge's Creek and Spanish Town on Virgin Gorda (each of which at some point in the Territory's history acted as the centre of administration for the islands) largely because of its instrinsic defensiveness in a highly turbulent era.
Tortola was never again attacked during the turbulent colonial era, and it is reasonable to surmise that the combination of the relatively low economic value of the Territory, and the relatively formidable defences, simply meant that it was an equally unattractive target for competing colonial powers on the one hand and privateers and pirates on the other.
The area of the Fort is heavily overgrown, and for safety reasons the government has sealed off the cistern to avoid the possibility of tourists falling in.
The hike to Fort Charlotte (there is no road) is considerably less arduous since the government cut a road from the top of Macnamara to the ridge, but it is still a good climb, and a machete to clear the bush that frequently overgrows the donkey track leading to the fort is usually a necessity during the wet season.