If you’re looking to escape New York City, there are two ways to experience the East End of Long Island in summer.

On one hand, the Hamptons, on the South Fork, can be downright wild. Drinks on the sandy beach. Naked (or mostly naked) pool parties. Celebrity-spotting at high-end boutiques. In the summertime, tiny towns such as Southampton, East Hampton, Bridgehampton, Amagansett and Sagaponack turn into New York City East, and they’re crawling with weekend hipsters who invade and bring the city to the country as they go.

On the other hand, if you like calm water, quiet beaches, and nice family-friendly afternoons, there is another option: The North Fork.

Here, in quiet towns and beaches, the vibe is diametrically different. Drinks usually are consumed in local dive bars. Pool parties usually comprise a bunch of families. The only celebrities you might see are local fishing legends. And almost none of the boutiques would even pretend to be high-end.

No wonder I love it so much.

As a kid growing up on Long Island, I’d come to the North Fork with my parents a few times every summer. Nowadays, though I don’t get back nearly as much as I’d like, it’s the only place I visit when I can. Here’s a rundown on what I consider to be must-see spots.


My absolute favorite of the North Fork towns is Greenport. The city’s history includes heydays in the oyster industry, but I like to think of it as a New England fishing town that went for a swim one night, crossed Long Island Sound and ended up on the tip of the North Fork of Long Island. The quaint village has a lively marina downtown. Elsewhere around the city, you’ll find other hallmarks of a great colonial-era town: Old buildings, open space, and families that have been there for generations.

Claudio’s, an iconic restaurant, from the water. Photos courtesy of discoverlongisland.com

One of my closest friends from high school now serves as a Village Trustee for Greenport, so I know it better than ever. This is a lucky development, especially since my prior knowledge of the city comprised the marina, a dive bar, the East End Seaport Museum, the mini-golf course, and a few B&B’s on the outskirts of town.

On recent visits, I’ve enjoyed stuffing my face with tacos and guzzling tequila (and margaritas) at Lucharito’s, a Mexican restaurant at the intersection of Main and Front streets near the marina.  I’ve also enjoyed staying at the Greenporter Hotel, a hip and modern boutique hotel downtown.

One of Greenport’s biggest summer draws is the Tall Ships America celebration. This event brings a number of old and replica schooners into town for people to watch and—in some cases—board.

The event is held every year around the same time; the featured ship for the 2015 iteration will be the Hermione frigate, an exact replica of the historic French ship that brought French general Marquis de Lafayette to the United States.

Southold wineries

The East End of Long Island is renowned (at least in the Eastern United States) as an up-and-coming wine region, and most of the wine is grown in vineyards across the North Fork. That means no trip to this part of the world is complete without stopping at least a few wineries to sample the literal fruits of local labor.

Most of the best wineries are located in the region west of Greenport, including a town named Southold..

When I was younger, my parents always gravitated toward Pindar Vineyards, one of the oldest in the region. The winery grows 17 different varietals and produces roughly a dozen different wines. Also interesting: Pindar runs 80 percent of all winery operations on wind power from a giant turbine.

Viewfinder Tip: For an intimate experience, sign up for a private tasting with the winemaker/owner at The Old Field; tastings include five wines and an individual cheese plate.

These days, my personal preference is The Old Field, a winery that practices sustainable farming and makes about 10 wines. One of the best things about The Old Field is that the same family has owned and operated the place for nearly 100 years. When you go into the winery’s modest tasting room to sample its wines, there’s a good chance you’ll be served by one of the members of the owning family. What’s more, the wine is good, too.

Another Southold winery worth visiting: Bedell Cellars. Here, the highlight actually isn’t the wine (sorry, winemaker); it’s the barn in which the tasting room sits. Built in 1919, the historic barn recently was named one of the “Top 25 Tasting Rooms in America” by Wine Enthusiast magazine. If it’s slow, tasting room personnel gladly will regale you with stories about some of the artifacts you see around the room.

The Big Duck

Finally, no visit to the East End of Long Island is complete without at least a short pilgrimage to the Big Duck. Technically speaking, this roadside attraction isn’t on the North Fork; it’s in Flanders, near Riverhead, where the two forks that comprise the back end of Long Island meet (or diverge).

As its name suggests, this icon is a building in the shape of a big white duck.

The structure was built in the 1930s by a duck farmer as a shop to sell ducks and duck eggs. It was added to the National Register of Historic Places in 1997. Today, the inside of the duck is home to a gift shop where visitors can purchase duck memorabilia and grab travel information. It’s kitschy. It’s garish. And it’s as much a part of North Fork history as anything.

What are your favorite off-the-beaten-path destinations around the country?