Shelter Island

Aside from water, one thing Shelter Island has in plentiful supply is history. The town’s timeline flows back to a 1620 land grant, with initial settlement beginning in 1652. Residences on Shelter Island can function as heirlooms, passed down by families from generation to generation, some dating to the Revolutionary War era. Sylvester Manor, built in the 1730s on that first tract of settled land, still stands today. By the 19th century, Shelter Island figured out its architectural character, something that remains relatively unchanged. Understanding the atmosphere of Shelter Island essentially comes down to one point: Despite zero stoplights, the place has yet to descend into utter chaos. It’s said about many places, but things really do move at a different speed on Shelter Island. The concept of “island time” is in full effect—if you’re always on the go, you may have to slow your roll to make it here.

It’s a running theme that even the singular Shelter Island cannot escape: seafood rules the East End. An active dining scene more or less revolves around aquatic fare, scoring top marks for lobster rolls, oysters, shrimp, and calamari. However, Shelter Island is still New York, meaning you can still get a slice of pizza or dip into other comforting sources of nourishment. Because of the inherent insular nature of Shelter Island, some restaurants rely on hyper-local fish markets and farms for their products. Speaking of, for a meal perhaps cheaper than you might indulge in at a restaurant, you too can stock up on fresh fish and shellfish, cheeses, eggs, honey, and produce. Grab some chocolates and flowers too. Retail space is famously non-existent, but if you’re the kind of person who loathes the sprawl of shopping malls, then Shelter Island may be the island to shelter on.