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Léon 1909 is one of Shelter Island’s most distinctive dining destinations, offering creative cuisine in a beautiful setting that combines old-world character with modern sensibility. Named for the year the property was established, Léon 1909 honors its history while delivering a dining experience that feels fresh, thoughtful, and completely of the moment. The menu showcases seasonal ingredients sourced from local Read more...

Isola brings the warmth and flavors of Italy to Shelter Island, offering handmade pasta, fresh seafood, and classic Italian dishes in a cozy, intimate setting that feels like a true neighborhood trattoria. The menu celebrates the best of Italian coastal cooking — think fresh linguine alle vongole, wood-fired preparations, vibrant antipasti, and desserts that will make you want to linger Read more...

225 acres of historic farmland dating to 1651. One of the oldest continuously farmed estates in America, with tours, community farming, and cultural events. Read more...

2,039 acres of forests, marshes, and shoreline managed by The Nature Conservancy. Miles of hiking trails and world-class birdwatching on the Atlantic Flyway. Read more...

Chic boutique hotel with a French Riviera feel right on the water. Hip, stylish, and uniquely Shelter Island. Read more...