This tiny, old-money village on the north side of Shelter Island is nestled between the forks ofLong Island‘s east end. Rent a kayak and paddle through the gorgeous Mashomack Wildlife Preserve, keeping an eye out for ospreys and the endangered piping plover. Residents of Dering Harbor can also brag that no one who calls the tiny village home lives below the poverty line, and in fact most live far, far above it, as the median family income is $98,750.