Though miles of Long Island Sound divides the two points, Southold was considered part of Connecticut for the first few decades after its 17th-century founding. Actually, the story goes that residents of Southold quite preferred the Connecticutter life until the then-colonial government forced their hands. Perhaps this has contributed to the hamlet—and the North Fork at large—feeling decidedly more coastal New England than Empire State. While not massive, Southold is large enough that it has distinct areas to either immerse yourself in hamlet life or to get away from it all. Like any worthwhile main street, Main Street is a hub for activity. However, turn off Main Street—or head further north past Route 48—and you’ll find things are more open and tranquil. If you grow tired of Earth entirely, spend an evening stargazing and staring toward far-off galaxies at Custer Observatory, the oldest structure of its kind on Long Island.

With street names like Albacore and Blue Marlin, it’s clear that Southold holds a place in its heart for creatures of the sea. Unfortunately for those creatures, Southold also has a place for them in its stomach. You wouldn’t be out on the East End if you couldn’t indulge in fresh seafood, and boy, does it not get any fresher than stopping at a local fish market to pick up the catch of the day steps removed from the water where anglers hauled it in. When dining out, options pretty much run the fanciness gamut from comfort food at cafes and taverns to prime provisions at eateries with Michelin star pedigrees. Of course, if you’re spending any amount of time in the North Fork, you’re going to want to sample the wares of neighborhood growers, be they gathered in a bushel or poured into a glass.