Nowhere in Jamaica is more off the beaten track than the Cockpits, and hiking and caving here is a real-life adventure, compared to the artificial thrills of zip lining and other 'adventure activities' around the island. Cockpit Country also provides a vital habitat for Jamaica's birdlife, with Windsor being a prime destination for birding.

Hiking

Just over 30 crow-flying kilometers from the roasting sunbathers of Montego Bay glowers a foreboding wilderness that challenges popular images of Jamaica as tame, well trodden and bereft of backcountry. Cockpit Country is a broad, barely penetrable thicket of dense foliage and intricate karst topography scattered with caves, hollows and conical hills that, metaphorically speaking, resembles an upturned egg carton.

A few hunters’ tracks and farmers' footpaths lead into and even across Cockpit Country. Most are faint paths, often overgrown, and hiking away from these trails can be dangerous going. The rocks are razor sharp and sinkholes are everywhere, often covered by decayed vegetation and ready to crumble underfoot. Never travel alone, as there is no one to hear you call for help should you fall into a sinkhole. Take lots of water: there is none to be had locally.

It is imperative you take a trusted guide. The one company that regularly organises tours in the Cockpits is the Southern Trelawny Environmental Agency, based in Rock Spring. STEA works with reputable local guides, simultaneously empowering local communities while giving visitors access to this little-explored corner of Jamaica. These locals are versed in ecotourism practices and know their way around these hills and caves. You’ll still need to bring stout walking shoes (or water shoes if caving), rain gear and a powerful flashlight in the event of a delay past sunset. Take warm clothing if you plan on staying overnight, as nights can get cold. Rates for guides vary based on hike length. STEA's most popular hike – and a great introduction to the Cockpits – is a 20km walk along the abandoned B10 road from Kinloss to Spring Garden that passes through Barbecue Bottom. Along the way, you get a real appreciation for the beautiful scenery – the honeycombed limestone cliffs and verdant valleys. It's a long hike, but with gentle inclines, so accessible to any moderately fit hiker, and with beautiful views – something you don't get hiking through the Cockpits' interior. Shorter hikes along that route are also possible.

Other trails through the Cockpits are little used and woefully overgrown. As locals drive more and walk less, the knowledge of the Cockpits' interior is becoming lost, which is great news for the ecosystem, but does mean that it's more and more difficult to find a guide who knows the longer routes. These include the arduous old military trail through the Cockpits connecting Windsor (in the north) with Troy (in the south), about 16km as the crow flies. It is a more difficult hike southbound, leading gradually uphill; an easier option is to begin in Troy and take the downhill route. A shorter loop hike is possible from Windsor, as is the Windsor–Quickstep trail.

Hiking the Troy–Windsor Trail

In the 1700s, Cockpit Country provided a savage refuge for runaway slaves – the Maroons – who waged an intermittent guerrilla war against the British colonizers. In an unsuccessful attempt to subjugate them, the British built a precarious military road across the Cockpits from Troy to Windsor that wound tortuously around hidden sinkholes and mosquito-infested jungle with paranoid place names including 'The Land of Look Behind’ and ‘Me No Sen You No Come.’ Dicing with danger, many British soldiers disappeared into the Cockpits never to return, victims of ambush or sheer exhaustion.

Miraculously, the Troy–Windsor road still exists, though what remains of the route today consists of a vague, overgrown trail that should not, under any circumstances, be tackled without a guide; experienced backcountry hikers have almost died here. If you mean to hike it, hire a guide with a machete from the Jamaican Caves Organisation, form a small group, and ensure that your party has a GPS, plenty of water (a minimum of 6L per person), mosquito repellent, high-energy snacks and a flashlight. Additionally, leave your name(s), contact information and estimated time of arrival with a reliable source. The trail measures 16km between the hamlet of Tyre and Windsor (although you need to add on an extra 3km at Tyre and 5km at Windsor to walk to the nearest reliable transport sources – Troy and Sherwood Content, respectively). It's very infrequently walked these days; sometimes not for years, so much of it is an arduous bush-whack, making it incredibly easy to get lost (not a good idea seeing as there are no settlements, no surface water and no chance of helicopter rescue.) Six hours is the minimum time required, eight hours is average, 10 hours isn’t uncommon. Start early!

Difficulties aside, the hike is one of Jamaica’s – nay, the Caribbean’s – greatest challenges. Tree cover and steep-sided hills block any expansive views, and you have to walk in single file, meaning the most interesting aspect of the walk lies in studying the remarkable endemism of the karst ecology. The Cockpit’s bloody history, as related by any good guide, is equally fascinating. Look out for the stone walls of the old road, which can be seen throughout much of the journey. The trail is easier done south to north starting from Troy. Beware, the mosquitoes are brutal!

For a guided hike with the JCO, you'll need a minimum of five people and your own transport. The cost is US$100 per person.

Spelunking

The Cockpits are laced with mostly uncharted caves that are a tempting draw for cavers. This is true adventure travel; guides lead trips into the better-known caverns, but past that, exploring is for experienced and properly outfitted cavers only. There is no rescue organization, and you enter caves at your own risk. The most accessible is the Windsor Cave at Windsor, though that's more interesting for its bats rather than rock formations. STEA organises an excellent two-hour caving excursion (US$50 per person) into the beautiful Painted Circuit Cave with an underground river that requires wading through.

The Jamaican Caves Organisation provides resources for the exploration of Jamaican caves, sinkholes and underground rivers. In 2005 the group completed a project to formally classify and evaluate more than 70 caves within Cockpit Country. They lead the occasional trip to the Peterkin-Rota cave system near Maldon in St James, involving some swimming (US$100 per person; minimum US$250). Transport is extra (US$100 depending on location).