Consisting of roughly 100 sq. mi., the island of Martha’s Vineyard has six classic New England towns, each with its own unique and unforgettable charm.
Established as an English settlement in 1642, Edgartown first rose to prominence during the golden age of whaling. To this day, stately captain’s manors – aproned by rose-entwined, white picket fences – stand in serene contrast to the energy and vibrance of North Water and Main Streets, where residents and visitors alike browse the town’s bistros and boutiques, art galleries, bookstores, curio shops and more.
Famous for the vibrant colors of its Gay Head Cliffs – as well as the iconic lighthouse perched atop them – Aquinnah is situated on the westernmost tip of Martha’s Vineyard. To this day, it serves as the centuries-old home of an indigenous tribe known as the Wampanoag.
Stone walls. Rolling hills. Stunning coastlines and a nature preserve. Welcome to Chillmark, where trademark sunsets cast a honey-rose hue across this historic region, including the quaint fishing village of Menemsha – where tourists and locals alike explore an eclectic array of curio shops, fashion boutiques and authentic New England eateries.
World renown for its vibrantly-colored gingerbread cottages and imposing, open-air Tabernacle, Oak Bluffs served for decades as a major center for summer religious retreats. Still a vibrant community with miles of public beaches and a verdant central park, this utterly charming town serves as one of only two ferry ports on the island; it also possesses another quite enviable distinction – it serves alcohol, which is not permitted in any other Vineyard community but one (Edgartown). Cheers!
Also commonly known as Tisbury, Vineyard Haven serves as the island’s main port of entry. But there’s more to this historic burg than the beauty of its harbor; just a block from the ferry, Main Street’s vibrant and eclectic shopping district awaits, brimming with an avant-garde, bohemian vibe perfect for those who seek a relaxed island experience.
Having faithfully preserved much of its 19th-century rural charm, West Tisbury is a nostalgic reminder that the independent spirit of “the stubborn New Englander” is alive and well. A small but quaint downtown is anchored by a “don’t-miss-it” general store known as Alley’s; across the way, there’s the Field Gallery, featuring large, whimsical dancing figures; and don’t forget to pay a visit to Grange Hall, a historic landmark built by the Vineyard Agricultural Society, which today serves as a gathering place for farmers, artisans, and local residents.