Lookout Park – also known as “Lookout Hill” because it sits at the highest point on Cuttyhunk Island – gets its name from its role as a naval lookout during World War II. From up here, soldiers could watch out for any German submarine activity in the surrounding waters.
These days, Lookout Park is best enjoyed as a quiet, scenic destination on a summer day trip to Cuttyhunk. A platform was built over the original bunker, providing a sweeping 360-degree view of the surrounding islands, Buzzards Bay, Vineyard Sound, and the Atlantic Ocean. Bring a lunch to enjoy at one of the picnic tables next to the observation platform, and don’t miss a spectacular sunset here over the water.
From Lookout Park, several footpaths and dirt roads lead toward the West End of Cuttyhunk Island. Head west on Tower Road to reach several more abandoned naval artillery batteries, which look out over the West End Pond and iconic Gosnold Monument. As you walk, please respect private property by obeying any posted signage along the roads.
Habitats & Wildlife
Cuttyhunk Island sits at the end of the Elizabeth Islands chain, at the entrance to Buzzards Bay and Vineyard Sound. Because of its open-water location, Cuttyhunk is a hotspot for birds. Look for seabirds like eiders, loons, and cormorants on the water and ospreys soaring through the air in summer. In the low grass and shrubs around Lookout Park, keep an eye out for warblers, sparrows, and other songbirds.