This restored military lookout and gun battery was named after Sir Thomas Shirley (1727–1800), who became the first Governor of the Leeward Islands in 1781. Get some historical background at the small interpretive center, then head uphill to explore the grounds for crumbling ruins and enjoy sweeping views. Admission includes entry to Nelson's Dockyard and the Dow's Hill Interpretation Centre.

　　As you drive uphill, the road forks with the left lane leading to the Blockhouse, where you can see the vestiges of officers' quarters and a powder magazine as well as enjoy superb views southwest, including Eric Clapton's vast Crossroads drug rehab center. If you turn right at the fork, the road dead ends at the Shirley Heights Lookout. The former guardhouse is now home to a restaurant-bar that hosts a famous Sunday-afternoon barbecue party with live bands. Views take in English Harbour and, on clear days, Montserrat and Guadeloupe. The moderate 1.5-mile Carpenters Trail runs from Galleon Beach up to Shirley Heights.