Shelter Island History & The Dickerson Family

The Story

A Rich and Remarkable Past

Before 1652 — The Manhansett People
Shelter Island was home to the Manhansett, a branch of the Montauk people. They called the island Ahaquatuwamock — “the island sheltered by islands.” The island was abundant with fish, shellfish, and game.

1652 — English Purchase
Nathaniel Sylvester and partners purchased Shelter Island from the Manhansett. Sylvester Manor — still standing today — became one of the earliest English estates on Long Island, a key hub of the colonial Atlantic trade network.

1675 — Quaker Refuge
Nathaniel Sylvester sheltered persecuted Quakers fleeing Puritan Massachusetts. Among those given refuge was Mary Dyer — who was later hanged in Boston. The island became a landmark in the history of American religious freedom.

1776 — The Culper Spy Ring
During the Revolutionary War, several islanders participated in the Culper Spy Ring — the intelligence network that fed George Washington critical information about British movements on Long Island.

1851 — Captain Josiah Perkins Dickerson
Shelter Island’s most celebrated son. Captain Dickerson commanded the clipper ship Flying Cloud on its legendary 1851 voyage from New York to San Francisco — setting a record of 89 days, 8 hours that stood for over 130 years.

1980 — Mashomack Preserve
The Nature Conservancy purchased 2,039 acres — over a third of the island — creating Mashomack Preserve. Today it protects one of the most ecologically significant landscapes in the northeastern United States.

Today
Shelter Island remains one of the few places on Long Island without a traffic light. No chains, no big box stores — just farms, beaches, trails, and a community that has carefully protected its character for generations. The ferries still run 365 days a year.