Martha's Vineyard

The ferry from Woods Hole takes just forty-five minutes, but it felt like crossing into a different decade. Lia and I stepped off in Vineyard Haven with bicycles instead of a rental car, having read enough to know that the island rewards a slower pace than the mainland allows. Martha’s Vineyard sits a few miles off Cape Cod, an island of clay cliffs, weathered shingle cottages, and small harbor towns that have resisted, with real effort, the kind of overdevelopment that swallowed much of the nearby coast.

Oak Bluffs and the gingerbread cottages

Our first stop was Oak Bluffs, where more than three hundred candy-colored Victorian cottages cluster around a central tabernacle, built originally as a Methodist camp meeting ground in the 1860s and now one of the most photographed streets in New England. We wheeled our bikes slowly past porches trimmed in lavender, mint, and rose-pink gingerbread, half expecting someone to ask us to leave — it felt too perfectly composed to be a real neighborhood people actually lived in. Down at the harbor we rode the Flying Horses Carousel, the oldest platform carousel still operating in the country, its hand-carved horses creaking pleasantly on their brass poles, and ate a lobster roll on the harbor wall while the evening ferry pulled in.

Aquinnah cliffs and the south shore beaches

The next day we biked the long, flat road out to Aquinnah, on the island’s western tip, where the Gay Head cliffs rise in bands of red, orange, and gray clay above the Atlantic — sacred ground to the Wampanoag Tribe, whose small museum and lighthouse sit at the cliff’s edge. We climbed down to the beach below, the clay staining our feet a faint rust color, and swam in water colder than we expected for August. On the ride back we stopped at South Beach near Edgartown, a wide stretch of Atlantic-facing sand backed by dunes and beach grass, utterly different from Oak Bluffs’ busy harborfront, and lay there until the light went low and gold over the water.

Getting There

Ferries to Martha’s Vineyard depart year-round from Woods Hole on Cape Cod, a crossing of about forty-five minutes, with seasonal boats also running from Hyannis, New Bedford, and Falmouth; reservations for cars fill up fast in summer, which is exactly why we left ours on the mainland. Cape Air offers short flights from Boston to Martha’s Vineyard Airport for those short on time. Once on the island, an extensive bike path network and a reliable seasonal bus service make a car genuinely unnecessary.