You can get a taste of Cockpit Country by entering the narrow valley south of Falmouth. This passage, surrounded by towering cockpits, is accessed via Sherwood Content, a 20-minute drive south of Martha Brae. An unpaved single-track road leads from Sherwood Content to Windsor, near the head of the valley. It is technically possible to hike across the Cockpits from Windsor to Troy, but the trail is overgrown and reputable guides are essential. The charm of Windsor (population = 4 + dog) is its end-of-the-road remoteness, its verdant beauty and its importance as a natural habitat that lures birders and bat-lovers.
Sherwood Content is the birthplace of world-champion sprinter Usain Bolt, and you'll see signs honoring him and his searing speed dotted around. On the way to Windsor you'll pass the wall surrounding his parents' house and the cookshop run by his aunt Lilly in the hamlet of Coxheath.