Desmond and Carpenter Rock Trail, near Shirley HeightsStarting just before Galleons beach, there's some roadside parking. You'll see a trail marker on the right for the Lookout. As you get closer you'll see another sign that reads Desmond Trail. Take it up to Shirley Heights, where you'll find great views overlooking Falmouth and English Harbors.
But wait, don't head back the same way. Head down the paved road a 1/4 mile and find a dirt road on your right. Check out the cemetery on your right. More nice views. Of the harbor and a monument to soldiers lost during the English battles of the Carribean.
Head back to the dirt road and continue to follow it to the right. Check out the cliffs overlooking the Carribean Sea . Now a little searching around the cliffs edge and you'll find the Carpenter Rock Trail(White Trail Markers on the rocks) Steep at first, the trail quickly easy to a steady descent. The views are nothing less than spectacular. They take you right to sea level where we were able to cool off in some tidal pools cut into the rocks. The trail leads you all the way back to Galleon Beach. Walk along the beach til you get to the gate house. Take the road about 100 yards back to the parking lot. About 2 1/2 miles and some great pics and memories.