Will Guidara helped define a new caliber of high-touch hospitality as the front-of-house impresario behind New York’s Eleven Madison Park, one of the most acclaimed restaurants in the U.S.—ranked first, in 2017, on the World’s 50 Best Restaurants list—where a waiter might anticipate your drink order from studying your social-media feed and a tableside card trick was once part of the meal.
Its casual sibling, the NoMad, was as celebrated for its bacchanalian parties as for chef-partner Daniel Humm’s foie gras–stuffed roast chickens.
In July 2019, Guidara and Humm announced the end of their eight-year partnership. It was a bombshell in the restaurant world. Guidara would eventually sell his shares in the Make It Nice restaurant group, the business they’d built together, before Humm transitioned Eleven Madison Park to an entirely vegan menu (and the NoMad shut down).
Guidara’s Next Act
Guidara, meanwhile, began planning a new solo career. Ideas for three separate New York restaurant projects were percolating by the time the pandemic hit. As the city entered lockdown in the spring of 2020, they all came to a standstill. Guidara escaped to his weekend home up the Hudson River for what he thought might be a few weeks. He wound up settling in for the long haul.
“The more time I spent up here, the more I realized I just love it, and I wanted to build my entire life up here,” he says from his home in Kingston, New York, approximately 32 miles northwest of Millbrook. Guidara made a split-second decision to abandon all of his big-city plans and focus instead on launching an epicurean hotel in the country.
By the end of 2020, he’d found the perfect location for sale across the river from his home, near the village of Millbrook in Dutchess County, the 350-acre Migdale Castle estate, built in 1927 for Andrew Carnegie’s only daughter, Margaret, and occupied until recently by billionaire art dealer Guy Wildenstein and his family.
The Wildensteins, who bought the property in 2000, spent $50 million renovating their 34,549-square-foot, 29-room mansion, adding a home theater, a 43-foot indoor swimming pool, and a pub bar imported from England. The grounds have tennis courts, two ponds, an organic vegetable garden, and a medieval-style thatched-roof hut for cooking barbeque.
Guidara and his silent partners—he won’t say who his backers are—secured an option to buy the property, listed at $20 million, pending approval of a zoning change to commercial use.
According to a lavishly illustrated prospectus for Second Mountain, as it would come to be called, Guidara dreamed of creating a Relais & Châteaux–grade hospitality experience, “following in the footsteps of America’s great resort destinations such as Blackberry Farm, Twin Farms, and Post Ranch Inn.” It was promised to be “the finest resort within a short drive from New York City,” with 77 rooms, suites, cabins, cottages, “rental pool units,” glamping tents, and “unparalleled” dining experiences from Brian Lockwood, a former chef de cuisine of the NoMad. The culinary offerings would include ingredients sourced on the property and a “best-in-class” beverage program centered on fine wine kept in the castle’s 5,000-bottle brick cellar.
In early 2021, Guidara presented his Migdale proposal to the Millbrook community, expecting a warm reception. Things did not go exactly as he’d planned.
The Millbrook Mystique
Millbrook may be one of the most exclusive, and discrete, rural enclaves you’ve never heard of—a bucolic land of rolling horse farms, private clubs, and gated compounds. For more than a century—ever since Henry Flagler and other robber barons of the Gilded Age built the first sprawling estates—captains of industry have pampered themselves here, hidden from view up long private roads. Millbrook’s annual foxhunt, held every fall since the 1890s, is part of the fabric of the town.
“If you buy a home that’s in the right of way of the hunt you need to sign away right of way or they won’t sell you the house,” says a recent addition to the community, who bought a weekend home there in 2019, “which means you literally need to allow folks to chase foxes through your property on horses, dressed like British soldiers.”
Apart from a few small bed-and-breakfasts, there’s no place to stay in and around the village of Millbrook. (An abandoned motel is currently awaiting redevelopment.) And the area’s wealthiest residents would prefer that it stay that way.
Over the last year Guidara’s proposal has split greater Millbrook—population 4,741 in the last census—into warring factions, pitting local merchants hoping to bring more traffic to its antique stores, clothing boutiques, and retro diner against its landed and newly landed gentry, who would just as well keep the place to themselves. “They want to keep the town very simple and not bring in a lot of people; businesses in town suffer for it,” says a shopkeeper who requested anonymity because, as she says, “they’ll run me out of town.”
In February 2021, Guidara called in to a Zoom meeting of the Planning Board of the Town of Washington, New York. (The village of Millbrook is officially part of the town of Washington, as the larger municipality is called, though most residents know the entire area as Millbrook.) “Hello, everyone, my name is Will Guidara,” he said. “I’m a restaurant person. I’ve been a restaurant person my entire life.”
Guidara explained the project’s inspiration. “I started thinking about, what could I do now as such that in 10 years I’d look back and say, Well, thank God for covid,” he said. He’d fallen in love with Migdale and with Millbrook. “I love the fact that the bank is the Millbrook Bank. I love the fact that the gas station is the Millbrook gas station,” he said. “I’m not a New York City developer who is looking to build something here and run it from afar. I do want to become a part of the community.”
He hoped the hotel’s restaurant would be a place where locals would go for a martini on a Wednesday night. He also promised to “bring in a lot of awesome people that are going to go downtown [into the village of Millbrook] and spend money.”
“They want to keep the town very simple and not bring in a lot of people; businesses in town suffer for it.”
The introduction seemed to go well. “I have to say that was one of the nicest presentations I’ve heard in a long time, and it really spoke to me quite a bit,” said Planning Board member James Cornell before the Zoom meeting ended.
And so Guidara was feeling cautiously optimistic a few weeks later when his lawyers began the process of applying for a “zoning amendment” for Migdale, an overlay district that would authorize its commercial use. He wasn’t expecting the backlash.
Bring on the Backlash
Word had spread through the community by the time Guidara’s follow-up Zoom presentation to the Planning Board drew a big crowd in late February. He offered more details on his plans for the site, unveiling a new residential real-estate component, a “proposed subdivision” with 23 homes for sale, each with access to Second Mountain’s hotel amenities.
After the meeting, some early supporters began to have second thoughts. “He did like a bait and switch,” says a weekend resident whose family has owned a home in the area for decades. “I think people were pretty blindsided.”
As a cautionary tale, Millbrook residents referenced a high-profile project nearby: Silo Ridge. This luxury housing development with eyesore mansions began rising on a golf course in neighboring Amenia in 2018. Tom Brady and Gisele Bündchen were among the first to buy one of its homes. “The theory was it was going to bring business into the village of Amenia, and it hasn’t brought in anybody at all,” says John Dyson, a former deputy mayor of New York (under Rudy Giuliani) and the founder of the Millbrook Vineyards & Winery, one of the area’s only real tourist destinations.
Soon, some of Millbrook’s most affluent residents were mobilizing to shut down Guidara’s plan. Dyson’s daughter and a few friends launched a nonprofit, Friends of the Town of Washington (FOTOW, for short), focused specifically on the fight against Second Mountain, collecting hundreds of names opposed to the zoning amendment.
Migdale’s immediate neighbors, Chanel chairman Alain Wertheimer and Bulgari heiress Veronica Bulgari, hired a law firm to represent their interests.
A flurry of letters and e-mails filed with the town clerk attacked the plan. One of them cited the “additional traffic burdens” that might “endanger the Town children’s safety.” Another called out its “deleterious environmental impacts.” “When the applicant stated in the February 25th Town Hall Zoom call that he wanted to ‘Bring the world to Millbrook,’ we knew he was looking in the wrong town,” wrote hedge-fund billionaire Bruce Kovner. “Millbrook is where most of us have raised our families and taken refuge to avoid the noise from the ‘rest of the world.’”
“This will be the beginning of the end of Millbrook as we know it,” added Olympic equestrian Peter Wylde. Bette Midler, whose Millbrook home was featured in Elle Décor in 2016, expressed concern for the town’s water supply while urging Guidara to consider alternative locations within the commercially zoned village.
“We’re also impressed by, and lucky enough to have enjoyed his hospitality credentials: we love eating delicious food, so would welcome new dining options,” read the letter signed by Midler and her husband, Martin von Haselberg.
FOTOW put up a slick Web site and posted an attack ad on YouTube, framing Guidara’s plans as “illegal” and a gateway to unchecked development. “A developer could literally build anything,” intones a narrator as images of a nascar racetrack, a water park, and a prison flash across the screen.
The community backlash blindsided Guidara. In April 2021, he withdrew the application for a zoning amendment he’d submitted weeks earlier, opting to “allow the Town an opportunity to amend its Comprehensive Plan” instead. A few months later the town hired outside consultants to study the issues and take a broad look at the community’s appetite for hospitality.
“People did not want an overlay district—there was a fear that it would set precedent for other people to come in and do the same thing,” says Guidara. “I had plenty of people who initially opposed the project call me and say, ‘We want you here—we just don’t want other people to follow you.’”
“Development Really Is the Devil”
Over the past year, Second Mountain has remained the hot topic in Millbrook. Public forums on Zoom have become heated, shattering its wholesome small-town veneer. “It’s unfortunate that it is so polarizing,” says Alex Casertano, a men’s-clothing designer raised in Millbrook who owns a small boutique in town and has spoken out in support of Guidara.
Midler, increasingly hostile to the project, called in to a meeting last September. “Hi, my name is Bette Midler, and I just want to say that to me, development really is the devil,” she said, before schooling her neighbors on Americans’ water usage and the threats to the local aquifer. “I want to talk about water—every American uses 90 gallons of water a day,” she said. “With the Migdale project sitting on the village aquifer, they will use up the aquifer in no time flat. This is a Trojan horse for large-scale development, and you let this project go forward at your own peril.”
In recent months the town’s hired consultants began developing a public-opinion survey on the future of hospitality in Millbrook. As the survey began circulating among residents this past spring, Guidara shared revised plans for Second Mountain with The Millerton News, a small local paper. Instead of adding a whole subdivision to the property, he said, he hoped to build a single residence—a home for himself and his wife, Christina Tosi, founder of the Milk Bar bakery in New York (known for its Compost Cookies and cake truffles), who gave birth to their first child last year.
“Since announcing our plans last March,” Guidara said recently in an official statement, “we’ve focused on listening to local feedback and refining our proposal in response to what we heard.”
Guidara projected a construction budget of $60 million and the eventual creation of 130 new full-time jobs. He’d commissioned his own environmental-impact study, he said, and he promised to remove the glamping tents, which spooked some residents with their hippie connotations. (Never mind that Timothy Leary moved into a 64-room Millbrook mansion in 1963 and ran a psychedelic commune there for the next five years.)
Guidara’s opponents responded with an e-mail blast presenting a very different picture of the proposed changes to Second Mountain, claiming that 40 homes and condos were still part of the plan. “Get the Facts. Take the Survey,” urged the e-mail. “Stop NYC Developers from Ruining Our Town.”
Though the town survey, covering hospitality broadly, wasn’t technically a referendum on Guidara’s plan, the results, announced in late May, don’t bode well for his resort. Sixty-six percent of the 674 respondents claimed to support new hospitality, but most opposed projects with more than 20 rooms.
Nevertheless, Guidara says he found the survey results “encouraging.” “We hope to hear from a broader sample of the community,” he says. He’s extended his purchase option on Migdale and is still hoping the town board might support some version of his plan.
“That house has been on and off the market for a very long time,” he says. “The reality is nobody is buying that as their primary residence. The people that can afford it? That’s not how they want to live anymore.” But whether or not it will experience a second life remains to be seen.
Jay Cheshes writes about art, culture, food, travel, and crime. He regularly contributes to The Wall Street Journal and WSJ. magazine. He trained as a chef at the Culinary Institute of America and has served as a restaurant critic for Gourmet and Time Out New York