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The Troy-Windsor Trail, Cockpit Country, Jamaica

Information on our current guiding services can be found at JCO Funding and Tours.


Advisory - Cockpit Country Bauxite Mining


The Cockpit Country of Jamaica, in its central region, can be traversed by only three routes: the Troy-Windsor Trail, the Quickstep Trail, and the now almost-lost Heading-Pantrepant Trail. Other than these three thin lines that offer a tenuous course through the inhospitable depths of the Cockpit Country, there are no "easy" ways across. "Easy" in this sense means that if you know what you're doing, and you have a guide, you won't die.

The Troy-Windsor Trail, Trelawny, Jamaica The Troy-Windsor Trail was built by soldiers of the British Army in the 1700's, during the Maroon Wars, as a "fast" way across the Cockpit Country. In addition to this, it also gave them control over two important sources of water: the head of the Martha Brae at Windsor, on the north side of the Cockpit Country; and the springs of Booth and Tyre in the south. Because of the geological nature of the Cockpit Country (karst), most waters run underground, far below what can be accessed with wells, and except for the perimeter, water can be scarce. Strategically, the Troy Trail was brilliant. It did not, however, succeed in the end, as the British would eventually be forced to sign a peace treaty with the Maroons, of the western Cockpit Country, in 1738.

Untold hours were spent on the creation of this military trail, by poor British conscripts, in an attempt by the upper-class overlords of Jamaica to drive the Maroons back to slavery. The Maroons, victorious, had the better part of it; the average life-span of British soldiers was 3 years after their arrival in Jamaica. Nevertheless, what they built endures.

The quality of the stone embankments that support the trail, as it contours around the many steep hills, is a testament to those British soldiers who died in the making of it. Even in its bushed-up, degraded state, the trail remains impressive. Although only a metre wide in most places, the trail snakes and contours through some of the nastiest terrain on Earth. It is hard to imagine how the original survey of the trail was done, several centuries ago, when a compass and sextant were hi-tech, but the building of it, in a place that has no surface water, no readily available food, and many mosquitoes, can be imagined by anyone who has visited the Cockpit Country; those assigned to the job were lucky to last for 3 years in Jamaica.

Although the trail endures, following it can be a problem. It is seldom used these days and, at times, it leads the unwary astray.

Salla, one of our crew, was the foremost guide for the trail until his death, October 1, 2003. He had been raised in the Cockpit Country, long years ago, when the people of the hills had yet to move to the electricity and convenience of town. He remembered the Cockpit Country, and the Troy-Windsor Trail, as home. He knew every hill, every valley, and many of the trees. Salla was the expert.

Taylor and Stewart We've attempted to build on the base that Salla gave us. In particular, we have GPS georeferenced the trail, a task that has consumed many hours and has resulted in many scratches, bruises, and mosquito bites. The map shown above, a low-resolution copy of the best map currently in existence of the trail, is a product of that work. It has accompanying GPS track and waypoint files, referenced to WGS84. It is a small section of a map that has been created for the entire Cockpit Country, and has been created by layering the 1:50,000 Ja Metric Grid topo maps onto the best available Landsat series for the western/central parts of the island.

Even though we wish that all of the members of the JCO were wealthy beyond our wildest dreams, and that we could freely give away the knowledge that we have gained through the years, the fact remains that we are all relatively poor and constantly in need of funding to continue what we do. In pursuit of those needs, we are willing to share our data, knowledge, and guidance, in return for appropriate recompense. We are not overstating the case when we say that we are the experts on the Troy-Windsor Trail. We can supply the best guides, GPS data, and logistical assistance to those who wish to make the crossing. If you would like to hire us, great stuff; if not, the best of luck with it, and please remember to bring lots of water.

For rates and logistics, please check JCO Funding and Tours.

Many thanks to The National Land Agency of Jamaica for the use of the topo maps on this site.


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