Massoud began work in the family business on the North Fork at age 10. His earliest memories at Paumanok are of tracking his father’s footsteps in the vineyards, tying grapevines onto tomato stakes and pulling weeds.

His parents, Charles and Ursula, established the winery on 22 acres in 1983, when only a handful of wineries existed on Long Island. Today, the estate spans 125 acres and Paumanok, in which his brothers, Nabeel and Salim, are also involved, is one of the region’s most respected wineries, known for its Chenin Blanc and Bordeaux varieties.

“If it was a ballgame, you might say that Long Island is still in the third inning…we still have a ways to go.”

His parents never expected Kareem to take over the family business: “They basically told me to get a real job,” he says.

Despite an Ivy League degree and a promising start on Wall Street, Kareem was drawn back to life in the North Fork and the pursuit of wines unlike any in the world.

“It’s paradise here,” Kareem says. “We have the sea and an agricultural region with rich history and such a diverse community of farmers, artists and writers.”

The challenge of developing Long Island’s still nascent wine industry was also compelling.

“If it was a ballgame, you might say that Long Island wine is still in the third inning,” he says. “If, say, Napa is the ninth-inning standard, we still have a ways to go.”

What really excites Kareem is the variety of grapes that Paumanok utilizes.

“We can make all these different wines and do them all well,” he says. “And if balance, moderation and varietal character is what you desire, Long Island is the perfect place for that.”

In the next decade, the Massouds plan to expand vine plantings and increase production by another 50 percent.

“My daughter is now eight months old, and in 15 years, she’ll be coming up on her sweet 16,” Kareem says. “It would be great for her and my nieces and nephews to continue our family business. And for us to become a multigenerational family business that can support that many families.”

Meador is one of the most talked-about new winemakers in New York. Yet, his path to making his own wine has been rocky.

Following a varied career in finance, music and advertising, the longtime Manhattan resident relocated in 2011 to the North Fork where his wife, Carey, grew up. Meador landed an entry-level winemaking position and says he “just took to it.” The couple then purchased a 24-acre plot in Southold with a dilapidated farmhouse. They began to rebuild and plant vineyards.

Southold Farm + Cellar launched with a tongue-in-cheek Kickstarter campaign aimed at helping Meador plant unusual varieties like Teroldego, Lagrein and Goldmuskateller in a world “awash in grapes like Merlot and Chardonnay.” A few established locals bristled at the campaign, but it raised nearly $25,000 within a month.

“Full-on naked winemaking…no temperature control and exposure to every bit of the elements….”

With no vineyard or winemaking facility, Meador’s 2013 vintage was made with grapes from the only certified organic grape grower in Long Island and using borrowed tank space at a nearby winery. His quirky roster of wines, from a pétillant-naturel Chardonnay to a carbonic-maceration Cabernet Franc, quickly sold out at New York City restaurants and wine stores.

In 2015, Meador initiated plans to build a winery. However, the town of Southold claimed he lacked the necessary variances to begin the project. The town said that his farm winery license could not be used to sell wine from his tasting room. Still without winemaking facilities, Meador’s 2015 vintage, including some that use his first estate-grown grapes, were made under a tent pitched at a neighboring winery.

“Full-on naked winemaking,” he says. “No walls means no temperature control and exposure to every bit of the elements imaginable.”

It’s been a struggle, but Meador is hopeful.

“There’s this old joke about how the best way to become a millionaire in the wine industry is to start with $2 million,” he says. “But it doesn’t have to be true here. We weren’t millionaires, but we’ve been able to make it work and grow quite quickly. It’s still possible to get in here and do something spectacular.”

Born and raised in the heart of Napa Valley, the last place that Urbanik Koch imagined she would end up was Long Island. But after earning a degree in viticulture and oenology from UC Davis and winemaking stints in Burgundy and Napa, Urbanik Koch was looking for a change.

In 2006, she found an ad for an assistant winemaker that was willing to relocate. But when the North Fork’s Bedell Cellars contacted her, Urbanik Koch nearly declined on the spot.

“To be honest, New York wasn’t a leap that I was seeking out,” she says. “I knew very little about the region, and New York wine wasn’t really something I had been exposed to.”

Urbanik Koch agreed to visit the North Fork. She arrived with no expectations and left blown away by the wines.

“I knew it was an opportunity to be part of something really special, and if I didn’t come out here, I would always regret it.”

“There was so much more structure and intensity than I expected from what I thought was such a cold-climate region,” says Urbanik Koch. “The reds had so much ripeness and lushness, and the whites were so aromatic.”

By the end of the trip, she knew she had to accept the position. “You could see there was this evolution happening in the wine industry already,” she says. “I knew it was an opportunity to be part of something really special, and if I didn’t come out here, I would always regret it.”

After four years at Bedell, she joined Macari Vineyards as head winemaker in 2010.

“It was just a perfect fit,” she says. “Working with the Macaris has been a huge opportunity for me creatively. It’s a special family, and such a unique vineyard located right on the water.”

She admits New York can be a hard region for winemaking.

“It’s so much easier to make wine where the weather is perfect,” she says. “Here, the weather is never the same. Every year is a new adventure.”

Urbanik Koch finds the challenge enthralling.

“It’s such a young industry still here, there are few rules,” she says. “We’re still writing the history of the region. It’s not set in stone, and we’re creating the expectations.”

“You’ve got to be crazy to stay here,” Nappa says, describing the unpredictable weather, exorbitant land prices and oft-difficult political climate in Long Island that struggles with the growth of the wine industry. But, he says, “Long Island is still the most interesting place on the East Coast to grow grapes.”

Before settling in Long Island in 2007, Nappa racked up a list of degrees in agriculture, viticulture and enology, and also made wines throughout New Zealand, Southern Italy, California and Massachusetts.

Upon returning to the U.S., Nappa says he “tasted up and down the coast,” but that Long Island is “an incredible maritime climate that gives wines a natural cohesion. If you pick the right grapes at the right time here, you get a natural balance of flavors without having to add anything [like yeast or acid] to the wines.”

“Long Island is still the most interesting place on the East Coast to grow grapes.”

As head winemaker for Raphael as well as his namesake label, Anthony Nappa Wines, he represents two sides of Long Island’s wine industry.

Raphael is a no-expense spared, Italianate winery built in 2000 at the height of Long Island’s wine boom. It easily accommodates the weddings, limousines and buses that pour in. Since he began at Raphael in 2011, its wines, particularly its Sauvignon Blanc and Cabernet Franc, have become more nuanced and elegant. Nappa says his Raphael wines show quality and consistency across a broader spectrum of styles and varieties than his own label does.

Nappa’s personal label produces less than 2,000 cases of wine per year and is sold quietly in his cooperative tasting room, The Winemaker Studio. His label’s focus is entirely on quality rather than consistency.

“For my own brand, if we are able to make an exceptional Cabernet Sauvignon or Pinot Noir just once every 10 years, that’s fine,” he says.

Expressing hope for the future, Nappa says that Long Island is “the kind of place where the stars have to align for great wine to work out. But part of the growth of a region is just figuring it out, and I think we’re getting to the point where the stars are aligning.”