For some of you lovely people, this trip to Martha's Vineyard will be one of many cherished visits, but for others it will be your first. The Island is a very special place to the two of us and we would love to share some tips, secrets, favorite spots and local knowledge with you.
Ups and Downs
Residents often divide the Vineyard into up-Island and down-Island districts. Up-Island is the western area, which comprises the three rural towns of Aquinnah, Chilmark and West Tisbury. Down-Island is the eastern portion, home to the larger historic villages of Edgartown, Oak Bluffs and Vineyard Haven. The two terms come from the rich seagoing tradition of Martha’s Vineyard, which was once home to a bustling whaling industry : heading “up,” in nautical terms, takes you west because it’s further from zero degrees of longitude in Greenwich, England, home of the Prime Meridian.
In its 100 square miles, Martha’s Vineyard has six towns, each with its own proud history and unique character.
One Island : Six Towns
Edgartown Originally established in 1642 as Great Harbour, Edgartown occupies the southeastern corner of the island. It’s the oldest English settlement on Martha’s Vineyard and still the shire town, or county seat. Edgartown is famous for the white-painted captain’s houses and grand churches that speak to the great prosperity of the whaling era. The plains district south of the town center, near the popular expanse of South Beach, is known as Katama. Famous residents include: Teri and Ralf Pirozzi.
Oak Bluffs North of Edgartown are the two main ferry ports of Martha’s Vineyard, Oak Bluffs and Tisbury. Oak Bluffs, to the east, was once a district of Edgartown, but seceded and became a separate town in 1880. In its early years, Oak Bluffs developed as a center for summer religious retreats; one of its architectural treasures today is the Methodist Campground, an enclave of multicolored gingerbread cottages with the grand open-air Tabernacle in its central park. It's delightful.
Vineyard Haven Tisbury is the only Island town with two common names – known almost interchangeably as Vineyard Haven. Years ago, Tisbury was known by yet another historic name, Holmes Hole, the “hole” referring to the town’s natural harbor. During the days of coastal shipping before the creation of the Cape Cod Canal, Holmes Hole was one of the busiest shipping ports on the whole East Coast. Today, Vineyard Haven is still the island’s main port of entry.
West Tisbury Heading southwest from Vineyard Haven will take you to West Tisbury, another town that testifies to the stubbornly independent spirits of old New Englanders. As the name might suggest, West Tisbury used to be part of Tisbury, but it followed the lead of Oak Bluffs and split away from its parent town in 1892. West Tisbury has buckets of rural charm, and its smaller downtown center features the historic Alley’s General Store, where Ted Danson likes to hang out and feel important (because he is). West Tisbury is home to the Island’s historic Grange Hall, and to the grounds of the Martha’s Vineyard Agricultural Society, home to the popular fair held every August.
Chilmark Further Up-Island from West Tisbury is the town of Chilmark, known for its rolling hills and stone walls, nature preserves and wild coastlines. From the South Road you can look across pastures of grazing sheep to sandy southern beaches and the island of Noman’s Land, now a federal bird sanctuary closed to vistors; the rockier north shore offers views of the Elizabeth Islands chain. Chilmark includes the picture-postcard fishing village of Menemsha, and the best views of the sunset anywhere on the Vineyard.
Aquinnah, at the westernmost tip of Martha’s Vineyard, is best known to visitors as home of the brightly colored Gay Head Cliffs and, atop them, the historic Gay Head Lighthouse. The town encloses less than six square miles and has some 400 year-round residents; it is home to the lands of the commonwealth’s only federally recognized Native American tribe, the Wampanoag Tribe of Gay Head (Aquinnah). According to Wampanoag legend, the ancestral giant Moshup created the colorful clay deposits in the Cliffs by smashing whales against them.
Get Around
If you are bringing a vehicle over let me implore you to make ferry reservations now.
If you aren't bringing a car over but would like to rent one we highly recommend AA Rental. Special rates pending!
If two wheeled transpiration is more your bag, then we recommend Cutler Bikes in Edgartown (ask for Thor) or Anderson's in Oak Bluffs. Cycling is a lovely way to traverse the island, with a rich network of functional and recreational bicycle paths and trails running through the six towns.
If you plan on visiting the Island sans vehicle you still have options:
Vineyard Transit - the Island's public transportation service - is nothing to shake a stick at. 12 bus lines run at regular intervals at reasonable fares. It's an economic and efficient way to get around the Island.
If you need to call a taxi at any point, we recommend Lighthouse Taxi. All of the taxi options on island can get a little pricey - and will charge more for late night travel - but this is the best one!
Our favorite spots for lobster rolls, day hikes, lighthouse peeping and more. Just a taste - stay tuned for more!