The first in her family to pursue higher education, Jasmine Alonso is a student at Napa Valley College with hopes of transferring into UC Davis’ viticulture and enology program — widely considered the top in the country. In some ways, she’s following in the footsteps of her grandfather and father who, like many Mexican immigrants in Wine Country, spent their careers in vineyards.

The key difference is that a degree will enable Alonso to secure a higher-paying position and avoid the monotonous, backbreaking work of pruning vines, thinning shoots and picking grapes.

Vineyard work “is all my father’s ever really known, so I think he always wanted me to go to school, get a degree and do something for myself since he never got the opportunity to do that,” said Alonso, who also works part time at Nickel & Nickel Winery.

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Alonso is part of a generational shift occurring within California’s agricultural workforce where the offspring of farmworkers are pursuing alternative, gainful and fulfilling careers — a result of having more opportunities and education than their parents and grandparents did when they arrived in America. But this deviation is compounding the labor shortage in Napa Valley’s vineyards, which has already been impacted by factors like immigration policy and the rising cost of living. One possible solution, mechanization, is fiercely contested by many Napa wineries, who are instead finding new ways to attract the next generation of vineyard workers.

Family photos hang on the walls of Leo Urena’s home he’s shared with his family on the property of Hudson Vineyards for the past 26 years in Napa, Calif. Friday, July 22, 2022.

A wall full of awards for Leo Urena’s prized pumpkins sits in the home he’s shared with his family on the property of Hudson Vineyards for the past 26 years in Napa, Calif. Friday, July 22, 2022.

Cristina Hudson, co-owner of Napa’s Hudson Ranch & Vineyards, said workers want more for their children. “They have aspirations for their kids to get out of the field,” she said. “And so they’re doing everything they can to make sure (their children) are educated and they have other opportunities.”

At the same time, many of Napa’s longtime vineyard workers are eyeing retirement — at Hudson, several employees are over 60 — and there aren’t enough young, skilled people to replace them. “We don’t see a lot of young people coming up the road and we certainly don’t see anyone who was born in Napa coming up and looking for a job,” Hudson said.

If a labor shortage continues, the most obvious solution is increased mechanization of the farming process, like harvesting wine grapes by machine. This is already happening in other regions, especially those producing mass-produced, lower-tiered wines, but that’s unlikely to happen throughout Napa Valley, said Pete Richmond, co-owner of vineyard management company Silverado Farming. Richmond has broached the idea of mechanization with his clients before, and they’ve all been adamantly resistant. The industry-wide perception is that regions utilizing mechanization are prioritizing quantity over quality, and many Napa wineries note their hand-picked grapes in marketing materials.

“In Napa specifically, we’re in such a luxury market that hand labor is still going to drive things for a foreseeable future,” Richmond said.

Plus, many vineyards, especially those planted on steep hillsides, can’t be farmed with machines.

“Talk to any high-end winery in Napa — it’s not going to happen,” said Steve Matthiasson, owner and winemaker of Matthiasson Wines, who has no plans to implement machinery. “We just have to pay more and have better working conditions and actually compete to attract labor.”

Leo Urena and his wife Gloria have coffee in the kitchen of the home they’ve lived in for the past 26 years on the property of Hudson Ranch & Vineyards.

But attracting labor has become an uphill battle, despite the fact that Napa Valley is the highest-paying county for vineyard labor in the country. Hudson, which flies a Mexican flag on its estate next to an American one, offers competitive wages — last year, the winery increased wages by 20% — as well as up to four weeks of paid vacation, health insurance, subsidized housing and scholarship opportunities for the children of employees. The company even offers a system where employees can turn down the Hudson benefits package if they’d rather make 20% more in wages, which the winery said happens often.

Hudson is still struggling to recruit qualified workers. Winery founder Lee Hudson blames the stigma that’s long been associated with agricultural work. This dates back to the migration to California in the 1930s when tens of thousands of Americans migrated from the drought-ridden Great Plains and Midwest following severe weather events known as the Dust Bowl. The only jobs these migrants could get was for seasonal farm labor. They were treated as outsiders, lived in poverty and faced harsh working conditions. The profession continues to receive less respect than other blue-collar jobs, Lee Hudson said.

“Socially, it’s recognized as the lowest rung on the ladder,” he said. “I don’t agree with it, but I think that plumbers are higher up on the social ladder than ag employees.”

Immigration policy is another hurdle. Due to tightened immigration laws from the Trump administration, it’s more difficult and expensive for workers to come to California from Mexico. Some vineyard management companies utilize the H-2A program, which allows employers to bring foreign nationals into the U.S. to fill temporary agricultural jobs. But the program has strict requirements — like providing transportation to and from Mexico, food and housing — that are difficult for most wineries.

Master gardener Leo Urena picks flowers for the tasting room in the garden at Hudson Ranch & Vineyards in Napa, Calif.

Rep. Mike Thompson, D-St. Helena, whose district includes Napa, doesn’t think immigration policy reform will happen anytime soon. “We’ve been trying to reform it forever, but it’s a tough nut to crack,” he said.

In the meantime, local programs are trying to close the gap. Fields of Opportunity, for example, exposes high school students to Napa’s wine industry through paid internships. Alonso participated in this program and landed an internship at the esteemed Opus One. There, she realized she wanted to focus on the viticulture side of the business.

Agricultural nonprofit Ag Health Benefits Alliance offers a scholarship program to farmworkers and their families for pursuing higher education or vocational opportunities. The program is in its third year, but executive director Becky Barlow hasn’t received a single application for a vineyard employee. “It’s always been for their children,” she said.

Alonso, who also received a scholarship from Ag Health, is an anomaly, Barlow added. Very few of the applicants are pursuing degrees in viticulture, instead setting their sights away from the fields and on careers like criminal justice. “The older generation, that’s what got them here and it became their way of life,” said Barlow. “It’s just such hard physical labor that I don’t think it’s an attractive career.”

With few solutions on the table, wineries and wine growers are seeking new ways to make labor more efficient and less physically demanding. “Recruiting and keeping experienced people here is a big deal,” said Matthiasson. “We’re trying to figure out how to change the work so that people don’t have to kill their bodies doing it.”

Vineyard manager Andres Urena, left, walks and talks through the grapevines with Hudson Vineyards owner Lee Hudson at Hudson Ranch & Vineyards in Napa.

Both Matthiasson and Hudson have introduced small mechanized tools like electric pruning shears to cut down on labor and raised the vineyard trellising system so that workers don’t have to bend over to work. Matthiasson redesigned the trays used to harvest grapes so that they’re easier and lighter to pick up. He also rotates his workers through different jobs to avoid repetitive-motion injuries.

Silverado Farming starts every work day with stretching and a warm-up to reduce the risk of injury. The company introduced a profit-sharing program for full-time employees, which divides 10% of the net annual profit among staff based on the number of years worked and job title. In November, Silverado will also pay for a handful of employees to enter a 30-day English-immersion program. “We’re really trying to make people understand that we value them for being here,” Richmond said.

If these strategies become the standard throughout Napa Valley, Matthiasson believes the workers will come. “When I first started working in ag, the boss got mad at the foreman for not firing anyone that week. You don’t have three people a day knocking on your door and asking for work anymore,” he said.

“But if we pay more and create a better working environment, the next generation will want to do it.”

Jess Lander is a San Francisco Chronicle staff writer. Email: jess.lander@sfchronicle.com Twitter: @jesslander