A true harelegger—so named because of the foot speed needed to catch the ferries that are the only way on or off Shelter Island—needs to be born on island. Amanda Clark doesn’t qualify since she was born at nearby Southampton Hospital. But she’s never really lived anywhere else, and her roots run back to a paternal great-grandfather, who moved to Shelter Island to care take a private estate on what is now the Mashomack Nature Preserve. The diminutive Clark, who is disarmingly youthful even at 29, followed her older siblings onto the water. Her brother and sister left the sport for greener pastures—horseback riding, and soccer and lacrosse, respectively—but she was hooked. As soon as she was able, she would spend most of her free time sailing her Optimist out of the Shelter Island YC. Initially her dad would keep watch, pantomiming the competition in a small motorboat. “I don’t think I ever beat him,” Clark recalls with a smile. As a pre-teen, she would venture out on her own. She’d pack a sandwich, bike from her childhood home to the yacht club, launch her boat, and point her bow west or east, always sailing up current first. She’d stop for lunch on some remote beach—using her bailer as an anchor so she didn’t scratch the bottom of her boat—and then sail home.