Get to know Southold

Southold? In the North Fork? Seems incongruous, but it is a fact. Sandwiched in the middle of the Suffolk County town of the same name, Southold’s freeform shape makes it rich in coastline. It’s something that enables far more access to water than many if not all of Southold’s neighbors, either on the North Fork or across the way in the Hamptons. The Sound splashes up on the northern shore, with the Peconic doing the same on the southern. Meanwhile, a wealth of waterways lay everywhere in between. The hamlet is a flagship for the greater town of Southold, offering pristine waterfront properties, excellent kayaking and biking, and peaceful beaches. It casts a hometown vibe, albeit with some added heft. After all, not many sentences start with “I grew up in a small town” and end with “that has an opera house downtown.”

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Southold History & Culture

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 get away from it all. Like any worthwhile main street, Main Street is a hub for activity. However, turn off Main — 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.

Southold Dining & Shopping

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’ll want to sample the wares of neighborhood growers, whether gathered in a bushel or poured into a glass.