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. Chilmark's small, rural community is located toward the western end of Martha's Vineyard. Most of its land is devoted to residential and agricultural use.
At Menemsha, the last remnants of a fabled fishing fleet are tied up at the dock behind two fish markets where you can find the catch of the day. You can catch a bike ferry across to Lobsterville, take a catamaran trip to Cuttyhunk Island, or climb out on the jetty with a folding chair and some wine and cheese to watch a spectacular sunset. At the Chilmark Store, you might spot a celebrity from New York or Los Angeles sitting right besides a local in one of the rocking chairs on the porch.
The center of town houses a an old elementary schoolhouse, originally a one-room school built in 1850 and the current site of the Chilmark Police Station. There is also a tiny post office, a public library, a town hall built circa 1897, elemetary school and a handsome church built in 1843.
Also located in Chilmark is The Yard, a performing artists' colony tucked between hills and meadows in Chilmark. The Yard has become a major cultural force on the Vineyard, bringing in diverse acts to the tiny theatre as well as widening their presence through performances around the Island.