This quaint fishing village -- a happy medium between well-developed Cape Cod and isolated Nantucket -- offers pristine beaches, boutique shops, and a taste of the region's maritime past. Read more
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Edgartown and Oak Bluffs are picturesque New England seaside towns, but still have shopping and entertainment options, such as wine bars, ice cream parlors, and elegant boutiques. On the western side of the island, towns like Chilmark and Menemsha provide a more remote experience.