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I often run along an historical trail in English Harbour. Go to the Copper and Lumber hotel and walk through to the waters edge. Take the dinghy dock out by the wall and then follow the white stone markers. The run is extremely challenging with many very steep ups and downs, but the rewards of running past historical gun emplacements and always overlooking the Caribbean/Atlantic sea well make it worth it. The route is circular so you end up where you start.