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Shelter Island Craft Brewery is a welcome addition to the island’s food and drink scene, offering locally crafted beers brewed with the character and spirit of Shelter Island built right in. The taproom is a relaxed, welcoming space where you can sample seasonal and year-round brews, learn about the brewing process, and enjoy a cold pint in good company. From Read more...

The Shelter Island Heights Pharmacy is one of the island’s most beloved and historic landmarks, a classic American soda fountain and neighborhood café that has been a gathering place for Shelter Island residents and visitors for generations. Step inside and you’ll find a wonderfully preserved piece of American nostalgia — an old-fashioned soda counter, homemade ice cream, egg creams, milkshakes, Read more...

Heights Cafe and Wine Bar is one of Shelter Island Heights’ most inviting spots, offering a carefully curated wine list, creative small plates, and a relaxed neighborhood atmosphere that makes it the ideal destination for a casual evening on the island. The wine selection spans Old World and New World producers with a focus on interesting, food-friendly bottles by the Read more...

The 1901 Grill is a classic Shelter Island restaurant and bar, offering well-crafted American grill fare in a historic setting that nods to the island’s rich past. The menu features all the grill classics done right — prime burgers, fresh seafood, grilled steaks, seasonal salads, and hearty sandwiches — along with a bar program of craft cocktails, local beers, and Read more...

Opties and Dinghies is Shelter Island’s most nautically spirited bar and restaurant, offering cold drinks, casual food, and a laid-back waterfront atmosphere that perfectly captures the easy, sun-soaked vibe of island living. Named with a nod to the small sailboats that dot the island’s harbors, Opties and Dinghies draws a mix of boaters, beachgoers, and locals who come for the Read more...