The town of Flagstaff is located on the northwestern boundary of the Cockpit Country, approximately a one-hour drive from Montego Bay, and is the original site of one of the earliest Maroon settlements. The Maroons were runaway slaves that banded together and subsisted independently. In Jamaica, the Maroons are famous for having fought the British military during the Maroon War from about 1730 to 1738. The cockpit karst landscape of Cockpit Country provided natural fortresses from guerilla strikes and foraging expeditions were conducted. The Maroons were such a formidable force that the British sought a Peace Treaty with the Maroons, a document signed in 1738 at Petty River Bottom, near Flagstaff.

The community is home to The Flagstaff Heritage Tour & Trails. Flagstaff heritage tours are operated by an outfit called Cockpit Country Experience, which was developed by the Local Forest Management Committee (LFMC). The Cockpit Country’s LFMC is a co-management institution developed in partnership between the Jamaican Foresty Department and local residents. It is commited to the conservation of the forest’s resources and the development of heritage and cultural tourism offerings that create sustainable livelihoods and industries for the local community. Together, Cockpit Country LFMC members and residents strive to create both an enlightening experience for visitors as well as offer training in resource management, tourism and marketing, and economic development to the local community.

The history of Flagstaff is brought to life through viewings of Maroon and British burial sites; the place where the Peace Treaty between the Maroons and the British was originally signed; the former British parade and training grounds and barracks; the site of the old Hospital; and Petty River Bottom, where the Maroon’s campaign for freedom was memorialized.

Among the tours offered are the Dragoon Hole Trail, the Maroon Trail and the Cemetery Trail. Herbal gardens, healing mineral springs, exquisite flora and fauna, and historic landmarks are among the habitats visitors will experience, all of which are enhanced by the defining character of the area, its people.

At the community’s center is a lovely visitor center that offers shade and a place to rest in between hikes. On the lower level are bathrooms and a gift shop with locally made items. Lunch can be arranged at a nearby restaurant, although options tend to be limited.