Despite popular disbelief, hiking trails do exist in Cockpit Country, with well-organized guided tours on offer to point out rare plants and birds. Windsor, Albert Town and Flagstaff are the most accessible starting points, where you should hire a local guide – essential not only to stop you getting lost but also in case of accident. The main sixteen-kilometre trail starts at Windsor and runs straight through the middle to Troy on the southern fringes of Cockpit Country, though it gets very overgrown towards the middle. The first few kilometres are relatively easy, but in the heat of the day it’s an arduous eight-to-ten hour trek; you’re in the midst of foliage most of the time with few open vistas, and you’ll certainly feel a sense of achievement at the end. Alternatively, the first couple of hours from Windsor give you a pretty good idea, and if you set out from Troy, the trail is mostly downhill and a lot easier – the best plan is to base yourself at Windsor, hire a guide and get yourselves to Troy early enough to make the hike back before nightfall.
Another great option is a trip to the gorgeous village of Bunker’s Hill, from where you can take a walk to Dromilly Cave, and then to a picnic spot by the Clear River, with a deep pool and lunch of anything from pepperpot or janga (freshwater crayfish) soup, to rundown, roast yam and sweet potato. Most walks are fairly easy-going, but for longer treks you’ll need a stout pair of shoes or boots, a waterproof, something warm for the evening, a torch and water bottle – and don’t forget mosquito repellent. Allow double your usual walking time for chopping foliage.
Cavers find Cockpit Country irresistible, despite a lack of infrastructure. Around 250 caves network the area, but only Windsor is easily accessible, with cathedral-sized Quashie River Sink a tougher scramble down steep slopes – not for the unfit. Caving in Jamaica is a good source of information, as is Alan Fincham’s essential book Jamaica Underground, which lists all the island’s caves.