Kontokosta Winery

More than 40 wineries call the North Fork home, along with a brewery and distillery. Wineries are a mix of corporate and independent; if you’re traveling with a larger group, check with independent operators ahead of time, since many don’t allow buses or vans.

Kontokosta Winery is the island's easternmost winery, and one of the most beautiful properties in a region packed with Instagram-ready wineries. Its long, vineyard-flanked driveway makes for a dramatic entrance, and leads to an equally impressive tasting room housed in a large, airy farmhouse. For the ultimate North Fork experience, cross the sprawling backyard with your glass of award-winning Rosé or Sauvignon Blanc while drinking in the rural sweep of Long Island Sound.

The Old Field Vineyards

The Old Field Vineyards feels like you’re drinking wine on a friend’s farm, where chickens run free and you’re welcome to wander the grounds. Mattebella Vineyards is a small winemaker focusing on sustainable practices. Its impossibly quaint tasting area includes a cottage and patio overlooking rose bushes and endless vineyards, and the knowledable employees are happy to answer your burning wine questions. Sparkling Pointe specializes in sparkling wines, and the indoor tasting room is distinguished by airy white walls accentuated with crystal chandeliers and colorful artwork. If the weather’s nice, opt to do a tasting on the terrace while admiring rows of vineyards. Oenophiles can book a tour of the facility, from the cellar to the tank room.

Shinn Estate Vineyard and Farmhouse

Shinn Estate Vineyard and Farmhouse excels at reds, from Merlot to Cabernet Sauvignon. Tastings on the rustic outdoor patio are ideal, and include a self-guided vineyard tour. You can also join an official tour, which includes the barrel cellar. Even better, stay the night in one of the estate’s four guest rooms. Croteaux Vineyards produces only Rosé; its flower- and greenery-filled tasting barn, peppered with umbrella-topped tables, contributes to the sense that you’re in the south of France. Raphael and Bedell Cellars are also standouts for their rustic chic ambience and excellent wine.

What to Do

You could easily spend the entire weekend visiting wineries, but it's not the only option. Rent bikes from Dan’s Bike Rental, either to pedal to wineries or around Greenport. A number of wineries also hold yoga classes in their vineyards during the warmer months. There's no shortage of farms, and Harbes Family Farm is one of the largest with three locations. The main location in Mattituck offers 10 acres with horses, sheep, chickens, rabbits and more. It also features two corn mazes, hayrides, and a tasting room for adults.

Orient Beach State Park is located at the very end of the North Fork, and is just a 15-minute drive from Greenport. The beach is long enough so that it never feels crowded; in fact, if you visit during an off-peak time, you might have much of it to yourself. Either way, hiking paths lead to such finds as mussel beds or giant osprey nests in trees, while kayak rental is available from Eagle’s Neck Paddling Company. On the way back, stop by Lavender By the Bay to stock up on lavender supplies. Walk through the lavender fields when they’re in bloom (usually between early summer and fall) for an $8 entry fee.

Shelter Island

The North Ferry to Shelter Island is conveniently located next to the Long Island Rail Road, and the trip takes five minutes. Shelter Island is a worthwhile excursion; if the North Fork feels like a serene getaway, the island is even more so. Exploring it requires a car, unless you’re in good enough shape to bike hills and longer distances. Grab lunch at SALT Waterfront Bar & Grill next to a marina and chow down on steamed mussels and lobster rolls. Afterward, make your way over to Sunset Beach and head upstairs to the bar to enjoy sunset views over the water.

Back in Greenport, make time to pop into its dozens of boutiques and antique stores that line Front and Main streets. Verbena sells eclectic gifts, while Bealle & Bell is a go-to among industry insiders for its antique treasure trove; Thursdays are the best bet to score new weekly finds.

Nightlife is low-key, but many wineries provide live music in the evenings. You can also find live music in Greenport at Claudio’s Clam Bar, First & South and on Greenport’s waterfront.

Where to Eat

Shabby chic Love Lane Kitchen in Mattituck is a beloved breakfast and brunch spot; you can’t go wrong with the French toast or a lobster roll. The North Fork Table & Inn, a ten-minute drive from Greenport in Southold, serves destination-worthy farm-to-table fare in an upscale farmhouse setting. Options for lunch or dinner might include tuna sashimi or handmade ricotta cavatelli. Desserts tend to be artistic takes on savory dishes, such as a tapioca pudding resembling sunny side up eggs. If you can’t score a reservation, look for The North Fork Food Truck in the parking lot and order the lobster roll at least once. A side of North Fork Potato Chips are obligatory.

In Greenport, The Salamander General Store serves some of the best fried chicken around. Place your order an hour ahead of time, then bring your feast to the waterfront for a lunchtime picnic. For dinner, Noah’s is acclaimed for its seafood and small plates, and provides an interesting selection of local wines. The Frisky Oyster is another upscale option for dinner, and yes, oysters are a highlight. For more casual dining, Claudio's Clam Bar is an open-air dining spot right on the water, and the perfect spot for enjoying fresh seafood and local wine.

Where to Stay

If you’re coming by public transportation, the Greenporter Hotel is just across the street from the Long Island Rail Road and within walking distance of town. The eco-friendly hotel is quiet, comfortable and even has an outdoor pool. The Harberfront Inn is also situated in Greenport. Its simple but luxurious rooms offer a clear view of Peconic Bay, and amenities include a heated in-ground pool. Further out, The Blue Inn at North Forkis a good value and neighbors Lavendar By the Bay. Rooms include a kitchenette, there’s an outdoor pool, and breakfast is included.

When to Go

The best time to visit is between Memorial Day and harvest season in the fall.

Getting There and Around

The North Fork is about two hours by car, or three hours via the Long Island Rail Road from Penn Station to Greenport. The Hampton Jitney, an upscale bus service that stops in both Manhattan and Brooklyn, is another popular option, and also stops in Greenport next to the Long Island Rail Road station. 

If you didn’t drive out, consider renting a car in Greenport, or arrange for a bike rental. A handful of wineries are within easy biking distance. Many restaurants and businesses are also within easy walking distance if you’re staying in town.