When your town’s timeline predates the birth of the United States, that’s a justifiable source of local pride. Some key dates include 1620 (James I of England includes Shelter Island in the Plymouth Company’s original land grant); 1656 (persecuted Quakers begin to seek refuge on the island); 1730 (first town meeting); 1743 (first church built); 1791 (first school opens). Yes, things moved slowly in that century after the first colonists landed on Manhansack-aha-quash-awamock (“an island sheltered by islands”) in 1638 and encountered the Manhanset tribe. If it seems things still happen slowly here, that's just the draw. The new Shelter Island Historical Center, currently under construction, will house more than 100,000 artifacts detailing the island’s layered four-century pedigree. Beyond that history, Shelter Island’s culture is a lifestyle full of nature trail walks at Mashomack Preserve and sunny days sunbathing or kayaking at any of the fine beaches (Wades Beach and Crescent Beach are watched over by lifeguards). That’s what island life is about, after all.

An active dining scene revolves around seafood restaurants and the occasional wild-card joint, like Mexican food at Maria’s Kitchen and Lucharito’s. But mainly, Shelter Island is tops for lobster rolls, oysters, shrimp, and calamari. There are seafood towers and clam chowder aplenty at Little Creek Oyster Farm & Market. And 18 Bay earns raves for its Italian cuisine (all the pastas are house-made) and relies on local sources for its products, from Southold Fish Market to Sang Lee Farm to Condzella’s Farm. Speaking of which, the island is replete with farm stands, a few of them on the honor system; they’re the spots to stock up on fresh fish and shellfish, cheeses, chocolates, honey, eggs, flowers, and produce. It is widely accepted that Shelter Island isn’t a big draw for retail therapy, though the lighting, jewelry, and works of ceramicist John Pagliaro at Handwerklab Art Gallery are highly regarded.