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The view from above Main Street. Credit: David Benthal

For many transplants and second-home owners, their North Fork story begins wherever they had that first great experience here. It’s the weekend they spent in Greenport Village or that winery trip where they ended up making it no farther east than Mattituck.  

But the true story of settling on the North Fork begins at what is now a park in the hamlet of Southold, appropriately named Founders Landing. That’s where John Youngs, a Puritan minister, arrived with his family in the autumn of 1640, establishing the first English settlement here. The main settlement consisted of a four-acre lot with a church, built in the northeast corner of what is today the cemetery of First Presbyterian Church.

While Southold sometimes gets overlooked in favor of its neighbor to the east, the Village of Greenport, or points west that are closer to home for many visitors to this region, it remains a prime destination for people looking to escape New York City and plant new roots in the country.

That’s particularly true for people looking to eat, drink, live and breathe the North Fork.

The hamlet of Southold is home to North Fork Table & Inn, the restaurant consistently rated tops on Long Island by Zagat. The nearby Caci North Fork is a wine lover’s paradise, serving rustic Italian fare and boasting a wine list perennially ranked by Wine Spectator among the best in the area.

Both restaurants are ideal landing spots for wine country guests. Southold also lays claim to being the home of some of the region’s finest wineries. Sparkling Pointe, with the bubbly offerings reflected in its title, and Croteaux Vineyards, which bottles only rosé, provide perfect niche tasting spots for connoisseurs. The ambience at The Old Field Vineyards or the Tap Room at Corey Creek offer different unrivaled experiences.


Settled: 1640

Indian name: Yenicott

Name origin: Southwold, England

School nickname: First Settlers

Population: 5,748

Area: 11.3 square miles

ZIP code: 11971

Great lunch spots abound. There are Southold Fish Market — where you leave with a full belly and bag of fresh-caught local fish — and The North Fork Shack, which effortlessly blends the farm-to-table experience we’ve come to expect on the North Fork with Mediterranean influences. The banh mi at Wednesday’s Table on Main Road is also guaranteed to please.

Southold is also where many, visitors and residents alike, seek out the latest in home furnishings — from the rustic chic of White Flower Farmhouse to the mid-century modern offerings of touchGOODS. Every room of your house can be improved at 1670 Furniture House and Complement the Chef is sure to up your game in the kitchen.

Of course, the Southold experience begins for many with their first cup of coffee from North Fork Roasting Co. or first breakfast at Erik’s on the North Road.

You barely even need to step on land to experience all the hamlet has to offer. The still waters of Southold Bay and Jockey Creek become open highways for boaters and office spaces for fishermen. And Long Island Sound in Southold is home to Horton Point Lighthouse, a landmark worth checking out for both its history and its serene setting.

Three public beaches in Southold also call Long Island Sound: Town Beach, Kenny’s Beach and McCabe’s Beach. We’d tell you about many other great beaches along the Sound and bay, but that might get us in trouble with the locals.

Of course, after you’ve read this and made up your mind that Southold is the next place you’ll call home, scan these pages for advertisements from local real estate agents, who will help you find that dream destination. In Southold, everyone’s a first settler.

North Fork neighborhoods is a series of profiles for northforker magazine on the different communities in Riverhead and Southold towns. Up next in April is Wading River.