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Which of the 6 Martha’s Vineyard Towns is Best for You? A Guide.

A crowd of people enjoying drinks at an outdoor bar underneath umbrellas, next to a tall pale blue Victorian house with a wraparound porch.

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Unspoiled seaside settings, rolling hills, and a relaxed pace have long attracted visitors to the shores of Martha’s Vineyard. This is, after all, a small island; a wonderfully rural place to enjoy drives on country roads. Its 87 square miles is an oasis of old-world charm and natural beauty in equal measure, with both a summer season and year-round population.

Located about four miles off the southeast coast of Cape Cod, Massachusetts, quaint towns and fresh ocean breezes bring hordes of visitors every year. The two famously photogenic towns of Martha’s Vineyard include Oak Bluffs, with its colorful Victorian gingerbread houses, and Edgartown, with its stately brick homes.

The island of Martha’s Vineyard is divided into two main sections: the more populated “down-island” towns of Vineyard Haven, Oak Bluffs, and Edgartown, and the more rural “up-island” towns of West Tisbury, Chilmark, and Aquinnah. Home year-round fishermen and farmers, creatives and entrepreneurs, tradesmen and teachers — and a LOT of lawyers and surgeons in the summer — a strong sense of community and unique character is the draw for many to make a home here. 

Martha’s Vineyard is a great place to partake in the simple pleasures of walking, biking, fishing, boating, crabbing, beachcombing, grilling, or simply reading a book under a tree. 

And here’s something to know: despite its name, Martha’s Vineyard does not actually contain any vineyards, much to the chagrin of wine enthusiasts (and my husband in particular). But fear not, there is plenty of wine to drink, and hundreds of other things to do in these six wonderful Martha’s Vineyard towns.

Best Towns on Martha’s Vineyard

What are the best Martha’s Vineyard towns for families? 

Every single town on Martha’s Vineyard is very family-friendly, but Oak Bluffs has some delightful kids’ attractions like the carousel.

What’s the Martha’s Vineyard Town with the gingerbread houses?

Oak Bluffs is the town with the gingerbread houses, and the island takes great pride in these architectural gems.

What are the best Martha’s Vineyard towns with lots of things to do?

If you want to have lots of things to do nearby, I recommend staying in Oak Bluffs, Edgartown, or Vineyard Haven. These are the most hopping towns.

What are the quieter Martha’s Vineyard…

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