Shelter Island

Situated snugly between Long Island’s rural North Fork and its posh southern neighbor, the Hamptons, Shelter Island blends a balanced mix of both areas beckoning the rich, the famous and the common man alike. Lulled by the tides of its Peconic, Gardener’s and Shelter Island Bays, this 8,000-acre paradise offers pristine beaches, breathtaking water views, historic homes, hideaway inns and gourmet eateries in a truly unique setting.

Shelter Island was settled in 1652, by Nathaniel Sylvester, a wealthy sugar merchant from Barbados, who owned the entire island by 1673. Following his death, the island was divided among him family and further divided and sold until the finally boasting more than 20 families at the time of the island’s incorporation in 1730. Crude trails dotted the Island and there was no organized transportation as the population continued to grow. Residents would travel by rowboat to mainland points in modern day Southold, Orient and North Sea.

The American Revolution took quite a toll on the island as residents suffered under British occupiers who had decimated much of Shelter Island’s landscape but, in the years that followed, the population continued to slowly expand and, in 1790, records show that 177 free individuals and 24 slaves lived on the island.

As the population grew, a need for access to the mainland became more apparent and in 1828 a road was completed connecting two commercial ferry services, one connecting the island to the south and the other to the north. Not only did this road benefit Shelter Island’s residents, it became the first link between the North and South Forks, via Shelter Island.

Through the 1800s East End of Long Island bustled with maritime work and many Shelter Island residents worked in the wailing, shipbuilding and fishing industries and a number of men enlisted in Lincoln’s army during the Civil War.

By 1871, the character of the island began to change, as Shelter Island became a popular summer destination for outsiders beginning a rapid trend that transformed the island into the preferred resort destination that it is today. By the turn of the century, the existing ferry services had improved bringing and even greater influx of visitors to the island.

Today there are approximately 2,500 full time residents and the population, like the rest of the East End, swells to more than three times that figure.

More than one-third of the island has been set aside as the Nature Conservancy's Mashomack Nature Preserve, which makes a great destination for hiking and witnessing the island as it originally was nearly 400 years ago. Although island traffic can rival neighboring tourist spots during the height of the season, Shelter Island continues to maintain its peaceful, rural character, which makes it a truly precious destination.