Hilly Chilmark boasts the island's highest elevation. 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 was named for a town near Thomas Mayhew Sr.'s birthplace in England. It was established in 1671 along with Tisbury and Edgartown. It became a farming community, and by 1850 had 96 farms.
The Chilmark village of Menemsha is an authentic New England fishing village with several small shops and eating places. The town center, near Beetlebung Corner, offers a modern library, a general store, and a chocolate factory.