What's In A Name? Whooping Boys Hollow

Legend says the name Whooping Boys Hollow, about halfway between East Hampton and Sag Harbor off Route 114, comes from warring Native Americans passing along a trail, or restless spirits dwelling in the woods.

More likely, according to the Rev. Jacob E. Mallmann in "Shelter Island and its Presbyterian Church," it is named for the "parting whoop" let out at the spot in 1653 by braves carrying the body of Poggatacut, the Sachem of Shelter Island, to Montauk for burial. (Some sources say the year was 1651.)

North of Whooping Hollow Road, a 1935 state landmark sign (which has been moved over time with the widening of the highway) marks the site. It also calls attention to Sachem's Hole nearby, where the body of Poggatacut (also spelled "Poggaticut") was laid while the pallbearers took a break during the trek.

Montauk Indians passing the sacred site kept Sachem's Hole clear of leaves and debris for almost 200 years.

Lion Gardiner referred to Poggatacut as the "great Sachem of all long Iland." His influence passed to his younger brother, Chief Wyandanch of Montauk, when he died.

William Wallace Tooker, a noted ethnographer who made a lifelong study of the tribes of Long Island, notes, however, that the name Poggatacut appears in no other colonial document but Lion Gardiner's. The state sign refers also to "Buc-usk-kil," though the connection between Buckskill Road, a few miles away off Stephen Hand's Path, and Whooping Boys Hollow is unclear. Buckskill is apparently of European origin: a "kil" in Dutch is a creek or other water source.

The only reference to Buckskill in the East Hampton Library's Long Island Collection is from April 9, 1698, when the Town Board "did then order that the prison should be sett at ye end of bucks skell."