Cuttyhunk used to be a much bigger island.
Or it at least seemed that way, when I was small and running barefoot through the worn streets with herds of other island children, our parents plying the water for bass and releasing us on the humble stretch of land where it is impossible to get lost or disappear. In that way, Cuttyhunk was my first taste of freedom.
Getting to the island was always a perfect blend of nerve wracking and exciting. Nerve wracking because, like the island, the little swells in Buzzard’s Bay also appeared much larger than they actually were to a small child staring out at our wake from the cockpit, still developing my sea legs. Exciting because I knew we had packed Pop Tarts in the crates of food we were brining ashore, our provisions for the week since there is only one small market on the island – the only time I was allowed to eat them all year. But the excitement pervaded the sugary treats, because there is a strong sentimentality to the island, one that sticks with you permanently from the moment you step ashore.
That sentimentality stems from Cuttyhunk’s long and impressive history, one that you might not expect from such a small island and its quirky group of fishermen residents. Cuttyhunk is the outermost of the Elizabeth Islands, and one of only two out of the 16 that are not privately owned by the Forbes family. Much less trafficked than some of New England’s other cruising destinations, Cuttyhunk has been a sort of secret haven for anglers since a group of wealthy businessmen founded the Cuttyhunk Fishing Club in 1864. The club disbanded in 1921, war efforts taking precedence, and in 1941, the Coast Guard built defensive bunkers on the island to survey the ocean for Nazi U-boats.
Today, that history is still felt everywhere you go on the island. The bunkers are now picnic areas that you can explore, and the meeting place for the Fishing Club has been restored as a bed and breakfast. To travel to Cuttyhunk is to take a step back in time, where cellphone reception is spotty at best, the number of cars can be counted on one hand, and a one-room schoolhouse educates the children of the year-round residents. And above all else, fishing is still the glue that holds society together. The memories of running around carefree with friends made spontaneously, carving out our own fun in the absence of structured entertainment, have permanently established Cuttyhunk as my favorite cruising destination. It may not have any frills, but that’s the best part.