Chilmark boasts beautiful homes set on rolling land, rambling stone walls, grazing sheep, and one of the most beautiful of all Vineyard drives: Middle Road. The ancient stone fences, undulating landscape, and soaring ocean views suggest Ireland. The town provides some of the best hiking and photography on the island.

Chilmark’s small, rural community is located toward the western end of Martha’s Vineyard. The town center, near Beetlebung Corner, offers a modern library, a general store, and a chocolate factory. Most of its land is devoted to residential and agricultural use. At the Chilmark Store, you might spot a celebrity from New York or Los Angeles sitting right beside a local in one of the rocking chairs on the porch.