The 100 square miles of Martha’s Vineyard are home to six separate towns which have evolved six unique personalities since the first arrival of English settlers to the island in 1642. The island, with its beautiful beaches, nature preserves and historic villages, is a magical place to visit at any season. But one of the most unexpected delights for many newcomers is the rich variety and unique charms of these six individual towns.

Tisbury, Port of Entry
The three towns of Vineyard Haven, Edgartown and Oak Bluffs together are home to about three-quarters of the island’s year-round population of some 15,000 people. For most visitors, their first steps on the island will be in Vineyard Haven, also called Tisbury, because this is the main port of entry for the Steamship Authority ferries sailing from Woods Hole. (The SSA also runs ferries to Oak Bluffs, but only during the summer season.)

Vineyard Haven is the island town least buffeted by the dramatic population cycles of the summer and winter seasons. It’s a densely settled community, with a population that matches Edgartown’s but on one-quarter the land area.

One of the natural treasures of Vineyard Haven is its harbor, which is protected by two promontories of land known as East Chop and West Chop. “Chop” is an old word for jaws, and these two jutting landforms have left Vineyard Haven with a natural enclosure that made it one of the busiest harbors on the East Coast during the heydays of coastal schooners in the United States. Along that harbor are such working businesses as the island’s main ferry terminal, the island’s only gasoline and heating oil depot and the famous Gannon & Benjamin boatyard, one of the finest builders of classic wooden yachts in the United States.

The man-made treasures of Vineyard Haven speak mainly to the town’s history. A drive out to the West Chop point will take you to the lighthouse, and past impressive private homes with sweeping ocean views. A walking tour of downtown is a chance to enjoy such island landmarks as the Bunch of Grapes bookstore, recently honored as the best private bookstore in the United States, the Black Dog Tavern and Bakery (not a tavern in the sense you might expect, because Tisbury is a “dry” town) and bustling family businesses like the Net Result Fish Market.

Oak Bluffs, the First Resort
Before there was even a town named Oak Bluffs – back in the 1830s – Methodist congregations across New England would organize summer retreats to the outlying woods north of Edgartown, where they would spend a week in revival meetings, hearing as many as four sermons a day. Many found this setting so delightful, they started coming early on their camping trips and staying late. That early tradition of the “camp-meeting” really gave Martha’s Vineyard its start as a summer resort community.

As the Methodists expanded their summer visits, they first built wooden platforms for their tents, and then began building a community of colorful cottages around their open-air meeting center. Thus was born the island’s only truly original architectural style, known today as Campground Gothic Revival. Some 300 cottages with “gingerbread” scrollwork details and gaily-colored paint schemes still stand at the heart of Oak Bluffs, around the central Tabernacle with its graceful arches of wrought iron.

The historic path of this burgeoning summer resort so departed from Edgartown that in 1880 its residents split away, forming the town of Cottage City. The town took on the new name of Oak Bluffs in 1907.

From its revivalist beginnings, Oak Bluffs has grown to become the island’s liveliest center for after-hours entertainment, with a downtown district, called Circuit Avenue, bustling well into the wee hours on summer weekends. Oak Bluffs is also home to such landmarks as the Flying Horses, the nation’s oldest operating carousel, and Union Chapel, a remarkable octagonal structure that dates to 1870.

The Oak Bluffs harbor is known as the island’s favorite center for power boaters, with its long concrete dock and electrical hookup services. Oak Bluffs is also home to the island’s most impressive collection of public parks. The jewel of them all is Ocean Park, with a bandstand at the center from which concerts are given on alternating Sunday nights throughout the summer. Ocean Park is also the center for the August fireworks display which traditionally draws the biggest crowds of any single island event, and which marks the conclusion of the high summer season.

Edgartown, Whaling Center
Edgartown, the parent community to Oak Bluffs, is arguably the island’s toniest town today. And in a sense, it has always been. In the 1600s it was site of the island’s first English settlement, then called Great Harbour. In the 1800s, Edgartown was a world center for the whaling trade, and all along the harbor today are formidable mansions, built by the whaling captains and ship owners, that testify to the wealth of that era. Fans of traditional New England architecture will be in for a treat in areas like North Water Street, with its stretch of immaculate homes in the Federal, Colonial and Greek Revival styles.

Edgartown shares with Oak Bluffs the distinction of being a “wet” town, where alcohol sales are legal, but it’s not quite as lively a party scene in the summer. The downtown district has a modern movie theatre and a fine assortment of shops dealing in everything from gourmet foods to designer clothes and jewelry.

Along the Edgartown harbor is the yacht club, with a parade of impressive sailing craft that lasts all summer. And beside the town’s Memorial Wharf, which has a spacious public viewing platform on its roof, the Chappaquiddick ferry service takes cars and passengers back and forth all day to the island-within-an-island whose highlights include the remarkable Japanese garden, Mytoi, and the large coastal nature preserves cared for by The Trustees of Reservations.

West Tisbury, Athens of Agriculture
If the island has a town best known for its rural, agricultural heritage, it is West Tisbury, which lies just west of Edgartown. West Tisbury is home to the fairgrounds of the Martha’s Vineyard Agricultural Society, whose annual fair and livestock show is the place to be for four festive days every August.

Driving from Edgartown, the road to West Tisbury takes you past the 5,100 acres of the Manuel S. Correllus State Forest, a nature preserve originally created in 1908 in an attempt to save a dying species of bird called the heath hen. (The bird went extinct, but by happy accident the state forest turned out to be a critical bit of environmental protection: it was placed perfectly above the aquifer, the lens of groundwater that provides the island’s primary fresh water supply.) You’ll also pass a lovely pond with a former woolen mill, now headquarters for the Martha’s Vineyard Garden Club.

Driving from Vineyard Haven, the road to West Tisbury takes you past farms and fields that speak to the island’s agricultural heritage. In the downtown village center, you’ll find a white-steepled church, a quaint town hall that was once an academy for aspiring young mariners, and the famous Alley’s General Store, whose motto, “Dealers in Almost Everything,” pretty much sums up its mission as the last all-purpose retail outpost on the western end of the island. After your stop at Alley’s for a morning paper, a monkey wrench or a boogie board, be sure to wander across the street. There you’ll find the Field Gallery, its lawns dotted with whimsical dancing sculptures created by a beloved island artist, the late Tom Maley.

Chilmark, Rural Enclave
The visual trademark of Chilmark, just west of West Tisbury, might well be the stone walls that wind their way through rolling fields and forests, recalling the day when vast expanses of the island landscape were open land, devoted to sheep farming. You’ll still see a working sheep farm if you look south from the South Road across the fields of Allen Farm to sweeping vistas of the Atlantic.

Chilmark has two important town centers. One, at a place called Beetlebung Corner for the trees there, has its library, school and town hall. Just a ways to the north is Menemsha, a picturesque fishing village which, remarkably, has kept much of its old New England character. The beach at Menemsha draws people all summer long, and is especially popular as the best place on the island from which to watch a colorful sunset.

Aquinnah, A Town of 2 Nations
A year-round population of fewer than 400 people lives in Aquinnah, the most remote town at the southwestern tip of Martha’s Vineyard. This community was known as Gay Head until 1998, when townspeople voted to give their home a name which recalls its heritage as the native land of the Wampanoag Tribe. Aquinnah, in the Wampanoag language, means the land beneath the cliffs, and certainly a visual highlight of any trip to Martha’s Vineyard must be the spectacular formation known as the Gay Head Cliffs. A national landmark, this outcropping of colorful clay was created by the shearing force of the same glacier that formed the Vineyard some 20,000 years ago.

The island’s Wampanoags are the same tribe that famously greeted the first Pilgrims at Plymouth Rock. Originally they had half a dozen villages or more across the island; it is only at Aquinnah that they have managed to survive as a distinct Indian community. In 1978, the U.S. government granted federal recognition to the Wampanoag Tribe of Gay Head (Aquinnah), making it the only tribe so recognized in the state of Massachusetts. At the Wampanoag Tribal Center on Black Brook Road, a museum detailing the history of the Wampanoags on Martha’s Vineyard is open every summer.