Vineyard Island Towns

Aquinnah
Home to the Wampanoag tribe, Aquinnah sits at the Western most point of Martha’s Vineyard. Shop at the Cliffs for beautiful wampum, other native goods, and then visit the Wampanoag Cultural Center.

Just below the 1799 lighthouse, rise the cliffs - marvelous in their composition of clay and sand with colors that burst in the vibrant glow of Aquinnah’s sunsets.

Don’t miss: the Orange Peel Bakery where everything is fantastic, but Pizza night - where the community brings the toppings for homemade crusts and shares the pie family style - is out of this world.
Aquinnah
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Chilmark
It’s hard to think of Chilmark without thinking about Chilmark Chocolates, but those treats are only the beginning of what’s good in this up island village.

Across from the library and the community center, you’ll find the Chilmark Store with its incredible pizza and a rocking chair-filled porch that’s just made for sitting and shooting the breeze.

Chilmarkers enjoy two of the island’s most stunning beaches, Lucy Vincent and Squibnocket. And then, there’s Menemsha, a quaint fishing village where the boats pull up to the dock and unload their bounty right into the back door of Larsen’s fish market.

Don’t miss: grabbing dinner at the Homeport Restaurant back door and walking down to catch the sunset from Menemsha Beach.
Chilmark
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Edgartown
For an historic experience of a true New England whaling town, take in the beautiful architecture, the old captain’s houses, and the rose-bordered gardens of Edgartown.

After enjoying the great shopping and restaurants of downtown head out to Katama to play on the cool sands of South Beach.

Edgartown is home to the old-fashioned 4th of July parade and fireworks. And if you’re into living local, visit the FARM Institute for a real farm experience and Morning Glory Farm for incredible local produce and delectables.

Don’t miss: taking the ‘On Time’ ferry over to Chappy, the little island across the harbor from Edgartown, and head to Wasque Point and Cape Pogue for some great surfcasting.
Edgartown
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Oak Bluffs
Oak Bluffs is the place to go for entertainment. Circuit Avenue boasts great food, live music, and some lively taverns.

For the kids, visit the oldest carousel in the country - the Flying Horses, the arcade and, of course, miles of sand, sun, and surf at State and Inkwell beaches.

The Arts District has beautiful galleries and an Art Stroll that exhibits the creative talents of the islanders.

Be sure to amble through the Victorian Gingerbread Cottages in the Campground, especially on Illumination Night and during the evening sing-a-longs at the Tabernacle.

Don’t miss: the legendary fireworks in Ocean Park in late August.
Oak Bluffs
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Vineyard Haven
The definition of Vineyard Haven is charm. The village is home to the William Street Historic District, boutique shopping on Main Street, the world-renowned Bunch of Grapes bookstore, and the Black Dog Bakery.

For entertainment, find the Vineyard Playhouse that draws top actors, directors and plays from around the world and the vintage movie experience of the Capawock Theater.

Then, head out to West Chop to see the lighthouse or play a round at Mink Meadows Golf Course. Steeped in history, the Vineyard Haven Harbor is the main port of entry to the island.

Visitors and islanders alike enjoy the comings and goings of the authentic working waterfront. Don't miss: a bounty of fresh fish in the case plus shrimp cocktail, fried clams, lobster rolls, and signature sushi rolls at The Net Result.
Vineyard Haven
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West Tisbury
The agricultural center of the island, a drive through West Tisbury offers rolling hills, cow and sheep filled pastures, and wonderful ponds.

Don’t blink or you’ll miss the center of town. There’s great stuff to be found, especially Alley’s General Store and the Grange Hall - home of the famous West Tisbury Farmers’ Market and the Artisans’ Fair that both run summer through fall.

Town residents enjoy Lambert’s Cove on the north side and Long Point on the south shore. For the little ones, there’s easy swimming along the shore of Uncle Seth’s Pond.

The gem of this town, of course, is the stunning Ag Hall, and the Ag Fair that blooms on the island every August. Don’t miss: communing with Martha’s Vineyard nature on the north shore at Cedar Tree Neck Sanctuary.
West Tisbury
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