Noted for rolling hills, roaming wildlife, old stone walls and gorgeous coastline that create a scene straight out of a pastoral painting, Chilmark is a picturesque Up-Island town. Settled in 1660, and made a separate township in 1694, Chilmark is now a mainly residential town, with lots of farming and a small working harbor that creates a haven for fishing and boating.
There are a number of sanctuaries in Chilmark including Menemsha Hills, 211 acres of land protected by the Trustees of the Reservation and crisscrossed with walking paths that allow hikers to enjoy wooded groves and breezy coastline. Climb to the highest point of Martha’s Vineyard on Peaked Hill and take in the breathtaking views.
Chilmark also has several lovely beaches, including the public Menemsha beach and two beaches open to permanent and summer residents only.
Although attractions like the Chilmark Store, the library, the famous Chilmark chocolates (home of scrumptious chocolate covered blueberries) and the Chilmark Tavern are in more rural settings throughout the town; Menemsha is the real town establishment.
A quaint and picturesque fishing town along the Vineyard sound, Menemsha has long been a point of departure for draggers and lobstermen, as well as the site of the United States Coast Guard station. Indeed, this village is a prime spot to take a private vessel or to embark on a chartered fishing trip or boat cruise.
Thanks to this fishing boom, Menemsha is home to many restaurants and markets that serve up some of the freshest seafood on the island. Order a lobster steamed to order at Menemsha and Larsen’s Fish Markets or pick up fresh fish and live lobsters to bring home. The fried delicacies at The Bite, an unassuming shack on the way to Menemsha beach, are a must-have. Take your meal to the beach and have a picnic while watching the sunset, as Menemsha is renowned as the best place on the Vineyard to watch this spectacle.