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Martha’s Vineyard, located just seven miles off the coast of Cape Cod, feels like a world apart. This island has long attracted artists, presidents, and vacationers seeking something quieter than the mainland. With six distinct towns, each with its own style, visitors can explore everything from the stately streets of Edgartown, once a prosperous whaling port, to the laid-back vibe of Chilmark, where stone walls and sheep pastures stretch to the sea. The island’s scale encourages wandering, with scenic drives, bike paths, and walking trails linking beaches, farms, and storybook villages.

One of the most iconic sights on the island is the row of brightly colored gingerbread cottages in Oak Bluffs. Originally part of a Methodist summer camp in the 1800s, these tiny homes now make up one of the most photographed spots on Martha’s Vineyard. Right around the corner is the Flying Horses Carousel, the oldest operating platform carousel in the United States. Built in 1876, it still delights visitors with hand-carved horses and a brass ring game that keeps kids (and adults) coming back for another ride.

Martha’s Vineyard also offers dramatic natural landscapes. The clay cliffs of Aquinnah, sacred to the Wampanoag Tribe, rise above the Atlantic in shades of red, orange, and gray. Visitors can take in sweeping views from the nearby Gay Head Lighthouse, which was carefully relocated in 2015 to protect it from shoreline erosion. For a quieter experience, the Long Point Wildlife Refuge provides access to windswept beaches, freshwater ponds, and miles of undeveloped shoreline all accessible by a short trail or kayak.