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This Real-Deal Castle Is a Hidden Gem in Millbrook

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The story behind Wing Castle is straight out of The Princess Bride.

Like the 1987 fantasy adventure film (and the 1973 William Goldman novel before it), the plot begins with a farm boy. Peter Wing grew up in the quiet countryside on Wing Farm, a plot of land that had been in his family for more than 100 years. Although Wing did not embark on any life or death adventures — that we know of ­— like Westley did, he did meet and marry the love of his life.

On the day Wing proposed to his wife, Toni Ann, on the grounds of his family’s sprawling farm, he promised to build her a castle. Toni Ann said yes and, after their wedding in 1970, the two got to work on their dream home.

“Our goal was to build a home for ourselves,” Toni Ann, a physical therapist, explains. “But we wanted turrets, a moat, and towers, too.”

Wing Castle Millbrook Wing Castle Millbrook
Photos by Chris Mottalini

For Wing, an artist with no formal construction background, the project became his passion for the next 44 years of his life. Like Westley in The Princess Bride, he taught himself the skills he needed to lay the literal building blocks for what would eventually become a veritable castle in Dutchess County. At first, he and Toni Ann estimated that their abode would be a two-year project. In no time at all, however, they realized that their 23-year-old selves had vastly underestimated the scope of their endeavor.

“Stone work is grueling and tedious and slow,” Toni Ann says. “[Wing] was one guy doing it all.”

She’s not exaggerating, either. With the exception of helping hands here and there, Wing completed construction on the first phase of the castle all by himself. It took him 22 years to complete using mostly recycled materials from old barns and buildings, but, by the end of it, he and Toni Ann had an honest-to-goodness castle of their own in Millbrook. They built their residence on the remaining plot of land that Wing kept after selling the bulk of his family’s farm property to Millbrook Vineyards & Winery, which resides down the hill. Wing Castle boasts magnificent views not only of the winery, but of the Mohonk area and the Catskills as well.

Wing Castle Millbrook

Once Wing finally did complete the castle he had long envisioned for himself, his wife, and their two children, he realized he also needed a means of sustaining his family. So he commenced phase two, a bed and breakfast addition to the castle that would allow visitors to experience the wonder of Wing’s work for themselves.

“It’s been referred to as a living art project,” Toni Ann observes. “Every little section of it is detailed.”

Wing Castle Millbrook Wing Castle Millbrook

For Wing, little details are what kept his work interesting over the course of the next 22 years that it took to complete the bed and breakfast. During that time, he added four rooms to the castle and incorporated elements as intricate as mosaic murals and stained glass. To support himself and his family, he balanced the construction of his home with commissioned sculptures in the Hudson Valley. Yet his life’s true work was always the castle.

By 2013, Wing Castle was ready to welcome overnight guests into its four main residences: the Annex, the Dungeon, the Chamber Room, and the Tower Room. Each room has its own personality, and all feel like part of a veritable fairytale.

“You get a lot of wows around here,” Toni Ann admits. “It’s comical because what else can you say?”

Wing Castle Millbrook

True to her point, Wing Castle is the sort of place to which photos and words cannot do full justice. With its fortress-like construction, it appears as if it’s been a presence in Millbrook for centuries, not decades. In each room, visitors are transported into otherworldly portals and nooks where it seems all too possible for fairy godmothers to cast their spells and princesses to seek reprieve. In the Chamber Room, for instance, stained glass windows reflect light onto the antiquated tiled floors and grand wooden bedframe.

In the Tower Room, breathtaking mosaics harmonize alongside old-timey lanterns and rustic wood beams. Then there’s the Annex, a two-story residence with a balcony and courtyard that seems like exactly the sort of place that Cinderella might call home. It connects via an underground tunnel to the Dungeon, an aptly named room in the underground heart of the castle. Each of the rooms has a private bathroom, and many have private entrances as well.

Wing Castle Millbrook Wing Castle Millbrook

To say that Wing Castle is a masterpiece in the Hudson Valley is an understatement. Peter Wing spent 44 years of his life installing pipework, stacking stones, piecing together murals, and letting his artistic sensibilities guide him. Tragically, however, he only had a short time to enjoy his finished creation. He died in a fatal car accident in 2014.

“Peter being an artist and not an architect was able to make [Wing Castle] feel like it’s been here for centuries,” Toni Ann, who still runs the bed and breakfast with her son, explains. “It’s kind of magical. It brings you out of where you’re at into a level of peacefulness. It’s one man’s lifetime of art all in one package.”

Wing Castle Millbrook

While the rooms are the main attraction at Wing Castle throughout the year, the property is also open for tours from June through Labor Day during the summer. Walks take about 45 minutes and include stops at over-the-top, themed outbuildings to ogle stained glass mosaics and tiled dragons. They also traverse along the moat and the stone henge (yes, really) and allow guests to experience the panorama of the winery beyond. Because Wing Castle is a private residence, all visitors to the property must call ahead to confirm a tour.

Wing Castle Millbrook Wing Castle Millbrook

As far as overnight stays go, rooms run $200 per night, with the exception of the two-story Annex, which costs $300 per night. Toni Ann includes continental breakfast with each stay and adds that, for most guests, it’s part of the incentive to remain on the castle grounds and simply unwind.

“People tend to relax when they get here,” she observes. “We’ve got courtyards and gazebos for them to enjoy. It’s a one-of-a-kind thing.”

We can’t be certain, but we think Westley and Buttercup would approve.

Wing Castle
717 Bangall Rd, Millbrook


Related: This Proposed Museum Wants to Bring the Spirit of the Catskills Resorts Back to Life