The Up-Island Lowdown: Visiting Western Martha’s Vineyard

With so many things to do in downtown Edgartown, it can be tough to justify straying very far from North Water Street, especially on a shorter visit. Still, if you’re a veteran of these parts or just looking for a change of scenery, a trip up-island is well worth your time. When we say up-island, we mean the western part of Martha’s Vineyard: West Tisbury, Chilmark, Menemsha, and Aquinnah. Confused yet? The phrase “up-island” dates back to our whaling days, when latitude and longitude were crucial for navigation. The further up-island you go, the higher your coordinate of longitude.

Getting Up-Island from Edgartown

We’ll admit that heading up-island takes a bit more planning and travel time than a stroll to Edgartown Lighthouse, but, trust us — the extra effort pays off. These smaller towns run at a slower pace, with natural scenery as their main focal point. For a quick ride out of town, your best bet is to check out the Vineyard Transit Authority bus schedule — day passes are inexpensive, and buses run regularly from town to town all day during the summer. For total freedom at a higher price, you can charter your own Stagecoach Taxi for your person tour-de-island. Guests can always stop by the front desk for personalized help planning a day up-island.

There’s a lot of ground to cover over in those parts, but we consider these up-island attractions essential:

West Tisbury

A perfect stop on the way to or from the island’s western tip, West Tisbury’s limits reach the shore both north and south of downtown, covering a huge swath of central-western Martha’s Vineyard. With the people here scattered few and far between, this hamlet provides the perfect opportunity for a meandering stroll through nature.  Just outside the village lies the 70-acre Polly Hill Arboretum, where tree species from around the world thrive amidst beautiful stone walls and meadowlands. Split your outdoor time between the Arboretum and the Field Gallery, whose whimsical sculptures live in harmony with a green landscape.

Menemsha

For hundreds of years, the island’s freshest catches have been arriving daily from the tiny fishing village of Menemsha. Larsen’s Fish Market menu has all the classics cooked to order from clam chowder and lobster to stuffed scallops. Visit for lunch or stop by mid-afternoon to avoid the evening rush that accompanies Menemsha’s famous sunsets. A walk around this sand-swept town promises rewards in the form of lesser-known storefronts, ocean views, and solitude.

Chilmark

Just southeast of Menemsha, Chilmark is the place to stock up on farm-fresh up-island produce and treats. Chilmark Chocolates make a sweet gift (if you can resist eating them yourself), and the Chilmark General Store serves up top-notch breakfast sandwiches and gourmet pizza with seating on their covered porch. Expect a fair amount of company at both places — they’ve earned the fuss.

Aquinnah

Home to the famed Gay Head Lighthouse, Aquinnah marks the westernmost tip of Martha’s Vineyard. You’ve probably seen photos of this historic beacon atop copper-colored clay bluffs, but a camera just can’t do it justice. The shoreline changes constantly with the tides—so much so that the lighthouse has actually been moved back from its more precarious original location.