Explore Martha's Vineyard Towns

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... Click for more ...

AQUINNAH , also known by its former name Gay Head , is the site of the most dramatic natural phenomenon on Martha’s Vineyard – the Gay Head Cliffs. The western portion of Martha’s Vineyard is marked by boulders, sand and clay deposits from the glacier. But nothing is more dramatic than the colorful cliffs of clay at Aquinnah (Gay Head). The cliffs are open for public viewing, from a high point near the Gay Head Lighthouse . From this vantage point, there is water on three sides, and Noman’s Land can be seen to the south and the Elizabeth Islands (both parts of Dukes County, but mostly unoccupied) are on the opposite horizon. The view from here of the cliffs and the ... Click for more ...

Tisbury (also known as Vineyard Haven) is the most active year-round community, partly because it is the only year-round ferry port on Martha’s Vineyard. Most Vineyard Haven shops and restaurants remain open in the winter, unlike those in Oak Bluffs and Edgartown, which rely more heavily on summer tourist trade. Vineyard Haven — the village is the center of the town of Tisbury—has a rich and deep maritime tradition and was one of early New England’s busiest ports. In the modern era, Tisbury’s summer crowd has had a literary/journalistic bent with famous summer residents. Click for more ...

The first of the up-island towns, West Tisbury provides a gradual transition from the hustle of down-island to the bucolic tranquility of up-island. Although primarily rural, it still offers a variety of retail businesses along State Road. You can definitely get away from it all in West Tisbury, Martha’s Vineyard’s traditional farming community. All of the Vineyard takes its flora and fauna seriously, but never more so than in West Tisbury, where the trees that canopy the roads have a special protected status. The Island’s leading conservation groups all have properties within the town boundaries where visitors can take easy, peaceful hikes of varying duration. Click for more ...

Edgartown, Massachusetts is a walking town on on Martha’s Vineyard with a compact village center, but the town itself is a total of 35 square miles. It contains miles of waterfront, either on the beaches, harbor or Edgartown Great Pond , with homes often tucked down dirt roads that feel especially “last century.” Edgartown also contains a portion of the Island’s state forest , with abundant walking, hiking and mountain bike riding paths. The Town of Edgartown is an old whaling town that has reemerged as a charming village, characterized by elegant historic homes and churches. Main Street, Edgartown looks the way a Main Street in a small New England town should look... Click for more ...

Oak Bluffs, adjacent to Tisbury on Vineyard Sound, is renowned for its gingerbread, “carpenter Gothic” cottages. Appropriately, the town was incorporated in 1880 as Cottage City, then renamed Oak Bluffs in 1907 in recognition of its increasingly year-round character. The genesis of the town was a Methodist camp that today is a collection of colorful cottages centered on a park with a soaring Tabernacle, a forum for religious and artistic events. Like Vineyard Haven, Oak Bluffs is a shopper’s mecca. It is a favorite destination for families because of the range of attractions, including beaches, parks, a hip harbor front scene, and a bustling downtown. Click for more ...