Napoleon Madison built the Aquinnah Shop – the first food shop on the cliffs – in 1945. The tribe’s medicine man was married to Nanetta Vanderhoop, whose family owned the land atop the cliffs. Asked what things were like when she first got involved in the shop, niece Anne Vanderhoop Madison says, “I was mouthy then, because I was young. I would tell Uncle Poli what he should do.” Anne thought there should be a greater variety of things for sale, and certainly didn’t approve of Napoleon putting canned condensed milk in the customers’ coffee.
The main items were takeout hamburgers and hot dogs, and because electricity didn’t arrive in Gay Head until 1951, there was no refrigeration. That meant a trip to Cronig’s on Main Street in Vineyard Haven every day for fresh supplies.
Anne was fully in charge of the Aquinnah Shop by the late 1960s and grew the business, adding more tourist items to the shelves and filling out the menu while expanding the size of the building. Legions of young women – Islanders and wash-ashores – have benefitted from Anne’s training, becoming waitresses and hostesses, earning their summer money and leaving for the larger world with a valuable new skill in the fall.
Today Matthew “Cully” Vanderhoop (one of Anne’s sons) is the proprietor. Seventy years since it began, the shop now has a large dining area, with wide-ranging breakfast, lunch, and dinner menus, and a wonderful deck that hangs out over the cliff edge for a truly spectacular view of the water and cliffs.
That deck, which Anne calls “the precious patio,” offers the lucky diner a front-row seat for sunset – if they time their reservation correctly. For waiting diners, a few displays of Island history entertain. They include photos, memorabilia, and native artwork – alongside Cully’s brother Buddy Vanderhoop’s sixty-plus-pound striped bass mounted on the wall.