Coastal charm abounds from shore to shore on the storied island of Martha’s Vineyard. But among great expanses of beach, forest, and countryside, six seaside villages each offer their own personality and historic splendor.

The bustling villages on the eastern side of the island, or down-Island, will be most familiar to visitors, from beautiful Edgartown to Oak Bluffs to Vineyard Haven. And to the west, or up-Island, the remote villages of Aquinnah, Chilmark, and West Tisbury entice with quaint towns and rolling hillsides. (The directions hail from whaling days – when seamen heading “up” traveled west, seeing increasing numbers of longitude, while those heading “down” traveled east back to England.)

To truly explore each village, you would need more than a day, and with Tradewind Aviation’s regularly scheduled shuttles to Martha’s Vineyard and private charters, an easy getaway is always at your fingertips.

Below is a general overview of each destination, complete with recommendations for dining:

Edgartown

 Photo: Barry Peters

Photo: Barry Peters

With a picturesque port that regularly hosts yachts and sailing regattas, Edgartown is one of New England’s most sought-after coastal retreats. The elegant village in the southeast is home to a flourishing town center, grand churches built during the whaling era, the white-painted captains’ houses, and miles of scenic beaches accented by Edgartown Lighthouse. It is one of only two “wet” towns on the island, making for lively nightlife in the summer.

Must-try Restaurant: Atria, a polished local eatery with global inspiration and an ever-evolving menu. Try the Pay Day burger with black truffle aioli, arugula, forest mushrooms, red wine reduction, and seared foie gras.

Chilmark

Dramatic coastlines and sweeping hillsides define Chilmark, home to some of the best sunset views on the entire island. Along with lovely nature preserves, you can find pastures of grazing sheep, the rocky northern shore offering vistas of the Elizabeth Islands, and the charming fishing town of Menemsha with its little shops and fresh seafood restaurants. The village also encompasses the island of Noman’s Land, a federal bird sanctuary closed to visitors.

Must-try Restaurant: Larsen’s Fish Market, a quaint market-slash-restaurant located on the fishing docks of Menemsha. Try the littleneck and cherrystone clams.

Oak Bluffs

 Photo: Michele Schaffer

Photo: Michele Schaffer

Modern elegance meets rich history in Oak Bluffs, a lively harbor-side village extending inland from East Chop Light. A walk through town will take you to the multi-colored gingerbread cottages, displaying their whimsical, Victorian architecture, as well as the open-air Tabernacle, Union Chapel, and the oldest platform carousel in the nation. Great expanses of pristine beaches are the village’s main draw, and in the evenings, visitors can enjoy vibrant nightlife and late-night pastries at Back Door Donuts.

Must-try Restaurant: Red Cat Kitchen, a tucked-away eatery with bold, artistic presentations and a nightly-changing menu.

Vineyard Haven

A place for the arts, Vineyard Haven brims with galleries and free musical performances. A walk down Main Street will take you by the renowned Bunch of Grapes bookstore, exquisite shopping and dining, and just a block away, the Vineyard Playhouse. The village was once one of the busiest shipping ports on the East Coast and today remains the island’s main port of entry. It is also very interchangeably referred to as Tisbury.

Must-try Restaurant: Little House Café, an intimate establishment with a menu brimming with creative flavor. Try the fish tacos.

Aquinnah

Gay Head Cliffs in Aquinnah, Martha's Vineyard

Located at the westernmost point of Martha’s Vineyard, Aquinnah is home to the stunning Gay Head Cliffs (formed from colorful clay deposits) with Gay Head Lighthouse standing atop them. The village itself is less than six square miles and offers a tranquil way of life in the country. It also harbors the lands of the Wampanoag Native American Tribe of Gay Head.

Must-try Restaurant: Aquinnah Shop Restaurant, a vibrant oceanfront destination with expansive decks and both American and Native American dishes. Try the Codzolez codfish cakes topped with pico de gallo and guacamole.

West Tisbury

Not to be confused with Vineyard Haven, West Tisbury is a destination in itself. The idyllic village abounds with rural charm, highlighting a 4,000-acre state forest and the grounds of the annual Martha’s Vineyard Agricultural Society fair. In the small downtown center, you can find the historic Alley’s General Store catty-corner from the Field Gallery (you will know it by the dancing lawn sculptures), and for another bit of history, head down the street to Grange Hall.

Must-try Restaurant: Scottish Bakehouse, a health-conscious bakery serving everything from quinoa burgers to coconut tofu. Try the famous egg sandwich.