How to Properly Eat and Drink Your Way Through Long Island Wine Country


The North Fork of Long Island isn’t just about bachelorette parties frolicking through the vineyards in search of men. For the connoisseur interested in a pairing that doesn’t involve Tinder, the rural region known fondly as “Wine Country” offers so much more than a handful of crushed grapes.

You can take the Long Island Railroad all the way out to Orient Point, but hopping aboard the Hampton Jitney’s North Fork line may prove to be quickest way to the destination of your choice. Depending on the scene you’re looking for, it’s the best way to make the most of your time. And if it truly is a scene you’re after to capture the spirit of Long Island, there’s no better place to spend an entire day than Claudio’s (111 Main Street, Greenport; 631-477-0627). The massive waterside complex — parts of which date back to 1870 — features distinct dining areas including an outdoor deck where a live band often plays. On the off chance you’re traveling by boat from Manhattan, the restaurant even has a marina.

While the main dining room offers an assortment of seafood and steaks, Claudio’s Clam Bar (111 Main Street, Greenport; 631-477-1889) is where most patrons choose to saddle up with a Miami Vice and a plate of cherrystones. A sister spot, Crabby Jerry’s at Claudio’s (111 Main Street, Greenport; 631 477-8252) which is geared more toward families and offers more casual fare — think popcorn shrimp, sandwiches, and seafood platters.

If you’re traveling as far out as Greenport, you might as well chart a course across the water to Sunset Beach (35 Shore Road, Shelter Island Heights; 631-749-2001). A ferry service leaves from Greenport until 1 a.m. and can accommodate bicycles and cars. Grab a drink and proceed to pretend you’ve landed in the south of France. The hotel and restaurant features an array of activities, including Ping-Pong tables and the occasional petanque tournament, though no matter how busy the place feels it’s hard not to feel complete relaxation. You may leave a few bucks poorer, but the ambiance will have you feeling richer on the ride home.

If the sight of the sea makes you weak in the knees, award-winning food abounds nearby. The North Fork Table & Inn (57225 Route 25, Southold; 631-765-0177) is widely recognized as one of the best culinary retreats on Long Island (Gerry Hayden was a James Beard Award finalist this year). If you can snag a table, you’ll be rewarded with dishes like butter-poached lobster and sweet-corn risotto. Naturally, there’s seared local tuna and Crescent Farms Long Island duck breast. Whichever you choose, the restaurant has a curated red and white list that’ll save you the trouble of vineyard hopping from Southhold to Aquebogue.

If you’re not looking to drop a monthly paycheck on one meal, the North Fork also runs a food truck that cooks up grass-fed beef chili, lobster rolls, and a Berkshire pork roll.

Another notable Southold table you might want to grab is Erik’s Breakfast & Lunch (43715 County Road 48, Southold; 631-765-6264), which offers a picturesque patio dining not to mention much needed coffee if you’ve been traveling all day.

If you’re hellbent on spending a day planted at a picnic table, Pindar (7645 New York 25, Peconic; 631-734-6200) and Raphael Vineyard and Winery (39390 Main Road
Peconic; 631-765-1100)
are two serene scenes worth seeking among the crowd. In particular, Raphael’s Italian-style villa design and live music makes it exceptionally welcoming for out-of-towners.

A trip to Long Island wouldn’t feel complete without a stop at a diner. The timeless Riverhead Diner and Grill (87 East Main Street, Riverhead; 631-727-8001) offers satiating plates of bacon and eggs. It’s the perfect spot to check out before hopping on the bus back home or to cure a cabernet hangover from the night before. Either way, you’ll reminiscence with your friends about a trek well worth having taken.