Back in the early 1600s, a stunning island called Manhansack-aha-quash-awamock, meaning "an island sheltered by islands," was home to the peaceful Manhanset tribe. Their respected leader, Sachem Pogatticut, held great influence as the Grand Sachem of most of the tribes across Long Island.

Time slows down on this tiny island and nature takes center stage. Accessible only by ferry, this hidden gem boasts tranquil beaches, lush forests, and winding roads perfect for leisurely bike rides.

With its protected wetlands in Mashomack Preserve, Shelter Island offers a haven for birdwatchers and hikers alike, inviting visitors to reconnect with the simple joys of life surrounded by breathtaking coastal views.

Because of its maritime location, Long Island was home to the largest slave-holding population in the north from which Nathanial Sylvester’s 700-acre sugar cane operation on Shelter Island sadly profited extensively.