Travel Diaries: 36 Hours on Martha's Vineyard, Massachusetts
Massachusetts year after year. The Vineyard, with a history of presidential visitors, has a reputation as a respite for the elite, a narrative that prompted Gov. Ron DeSantis of Florida to send two planeloads of migrants there without warning last fall, throwing the island in the national spotlight once again. Despite the stereotypes, the Vineyard's many cultures — African American, Brazilian, Jamaican and islanders that go back dozens of generations or far more, including Native Americans — have come to redefine this longtime summer destination as a place of community and joy. ITINERARYFriday
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6 p.m. | See colorful cottages Catch Oak Bluffs, an eclectic town on the island's northeastern shore, as the sun begins to peek through the ornate cutouts of the gingerbread cottages that have lined the downtown streets for more than 160 years. The brightly colored houses were built by a Methodist movement for their growing community and mimic the tents its members originally gathered in. Many of the 300-plus original cottages can be found in Wesleyan Grove, the historic district encompassing the old campground. Afterward, stroll a few minutes east to admire some of Oak Bluffs' grandest homes, which line Ocean Park, including the Joe Overton House, a Victorian mansion built in 1875 that was eventually owned by a Black union organizer from the New York City neighborhood of Harlem, for whom it is named today. The house was a frequent destination for civil rights leaders, including Martin Luther King Jr., and is part of a vibrant African American history in Oak Bluffs.7 p.m. | Dine on the harbor Summer is on full display along Oak Bluffs harbor, where
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