Connecticut’s Winvian Farm Offers a Luxury Treehouse, a Helicopter Lounge, and Seed-to-Fork Dining

An aerial view of the Charter Oak (R), Helicopter (C), and Connecticut Yankee private cottage accommodations at Winvian Farm in Morris, Connecticut, where each of the 19 guest units has its own theme, architecture, and matching interior design. Courtesy of Winvian Farm

Extraordinary occasions call for unique locations. That was our mindset as we recently planned an escape to celebrate our 20th wedding anniversary.

We found many hotels offering a luxury wellness retreat and many others steeped in charm. Winvian Farm offers both indulgence and one-of-a-kind character with its 18 bespoke themed cottages and one luxury suite, seed-to-fork dining, a world-class spa, and grounds set in the hills of Litchfield County, Connecticut.

The entrance of Winvian Farm. Courtesy of Winvian Farm

Hospitality

The matriarch of this enchanted place is resort founder and owner Maggie Smith, who operates Winvian with her daughter Heather, son Win Smith III, and a team of long-serving “extended family” such as founding Executive Chef Chris Eddy (a protégé of restaurant luminaries Alain Ducasse and Daniel Boulud). Ms. Smith’s taste and style for hospitality trace back to her Hungarian and Irish ancestry and the large celebrations of extended family and friends that were common in her childhood.

Maggie Smith, the owner and operator of Winvian Farm. Courtesy of Winvian Farm

She raised four of her own kids in Greenwich, Connecticut, where her home was the gathering hub, constantly hosting large celebrations for family, friends, and the community. She would frequently travel with the kids to visit Grandma Vivian at her historic home and farm. The property was lovingly referred to as “Winvian,” combining her husband’s name “Win” (short for Winthrop) with her own. Before his death, Win was one of the founding partners and the former chairman of the Wall Street firm Merrill Lynch. The couple bought the property as a gentleman’s farm, a weekend and summer retreat to escape New York City.

After Vivian died, decisions needed to be made as to what to do with the epic but capital-intensive Winvian property. At that time, Ms. Smith’s own nest had just emptied, with her fourth adult child leaving home, and she was ready for the next chapter of her own story. So she took a risk, investing her time, energy, and capital into converting Winvian into a destination resort.

“The idea was to protect the property and preserve the Smith legacy for the children,” she explained, when we spoke by phone after my recent stay.

An aerial view of the gardens at Winvian Farm. Courtesy of Winvian Farm

She also wanted to share the historic property and her talent for hospitality with the wider public.

“My big goal was I wanted people to feel welcome and the warmth of the understated elegance ... to be able to kick back and enjoy themselves. Like their home, but the service is better!” she said.

After two and a half years of working with the town of Morris for the appropriate permits, commissioning 15 architects, and starting an ambitious construction build-out, Winvian Farm opened its doors in 2006.

It was a success, drawing a mix of weekenders from the surrounding U.S. northeast and eventually welcoming tourists from all over the world. Acknowledgment of her team’s achievements was solidified with membership in the prestigious Relais & Châteaux, an exclusive network of 580 of the world’s finest independent luxury hotels and restaurants. The resort has also won many accolades, including the highest AAA rating of five diamonds for both the hotel and restaurant.

The Stone Cottage. Courtesy of Winvian Farm

The Cottages

At the heart of the Winvian is the bespoke lodging. Unlike most hotels in which guest rooms are accessed from the main lobby and are mostly homogenized, at Winvian, there are 18 cottages and one suite spread throughout the hotel’s 120 acres, which sits adjacent to a 2,000-acre preserve. Each unit has its own set of bikes, an espresso machine, a tea kettle, a king-sized bed, a steam shower, and an oversized soaking tub. However, that’s where the similarities end.

The bedroom at the Beaver Lodge. Courtesy of Winvian Farm

Each cottage maintains its own theme, a winning concept pitched during a design contest that Ms. Smith organized with famed architect David Sellers.

In the resort’s press notes, she said, “One of my favorite and most memorable descriptions of Winvian Farm is that it is ‘where Norman Rockwell meets Alice in Wonderland!’ ... A childlike sense of awe and wonder often characterize the guest’s reaction.”

For example, one of the hardest cottages to reserve is the Tree House, a multistory structure situated in the forest canopy. If you conduct an internet search for U.S. treehouse hotels (which I highly recommend you do), Winvian’s website usually ranks on the first page and also is featured in most of the other articles on this quirky subject.

The Treehouse Cottage, one of the resort's most popular accommodations. Courtesy of Winvian Farm

Another wait-listed cottage is the Helicopter, which features a sprawling airport hangar-themed space that contains a retired U.S. Coast Guard Sikorsky Sea King Pelican HH3F rescue chopper—a nod to the local history of nearby Stratford, where Igor Sikorsky opened his original manufacturing facility (now owned by Lockheed Martin) in 1923 and is still making Black Hawk helicopters. In this cottage, the bed and bathroom are adjacent to the massive metal body of the chopper, and the interior of the helicopter has been converted into a lounge with a couch, flat-screen TV, and wet bar.

The patio at the Helicopter Cottage, with the nose of the retired U.S. Coast Guard Sikorsky Sea King Pelican HH3F rescue chopper, in the background. The interior of the helicopter has been refurbished as a lounge with a TV, couch, and wet bar. Courtesy of Winvian Farm

We stayed in the Secret Society cottage. From the front exterior, the dark-colored structure appears to be windowless with a Masonic architectural vibe. Upon entering the front door, we were surprised that the space was flooded with natural light from the clever stealth glass pyramid skylight roof situated over the entire second floor and king-size bed. After exploring the patio and other nooks and crannies of the intriguing space, we settled on the couch and enjoyed tea and a delicious charcuterie board, while streaming our favorite music through the cottage’s impressive stereo.

When we turned in for the evening, resting our heads on the pillows, we could see the night’s stars as if we were sleeping outside. In the morning, we woke among the trees of the forest through the skylight, though my wife chose to wear the provided eye mask to sleep in and not be disturbed by the light of dawn.

The Secret Society cottage. Courtesy of Winvian Farm

While each cottage is one-of-a-kind, some of the notables include Golf, Music, Beaver Lodge, Camping, the barn-inspired Charter Oak, the Mark Twain homage Connecticut Yankee, Library, Maritime, Stone, and Stable. Ms. Smith told me that the variety of rooms is “part of the intrigue of it, and draws people back. ... You can have a unique experience each time.”

Dining

We found the pace at Winvian to be set by the adventurous transitions through the property’s grounds between relaxing in our room and the very special dining at the main building. The light exercise piqued our appetites as we walked from our cottage to the main building, and then the post-meal stroll helped us digest the farm-fresh organic cuisine in our delightfully stuffed bellies.

Chef Patrick harvests fresh ingredients from the garden for the day's dining service. Courtesy of Winvian Farm

It was a beautiful routine of eating, enjoying the outdoors, resting in the cottage, and then repeating. Having this time to explore the large grassy spaces, the pond, and the gardens and admire the architecture of the various cottages set us in a mood wherein the worries of the outside world faded as we looked forward to the next culinary surprise.

The main building, in which the formal dining room and casual tavern are located. Courtesy of Winvian Farm

Executive Chef Chris Eddy and his team offer inventive prix fixe meals, with many of the ingredients harvested from the farm earlier in the day. It’s an experience that delights and exceeds expectations with unexpected nibbles, palate cleansers, and artistic culinary presentations. As we unwound in the 18th-century dining rooms, we appreciated the exceptional attention to detail without the formality of similar-caliber restaurants.

Plates at Winvian delight in taste and presentation. Courtesy of Winvian Farm

The Spa

The spa's dedicated building. Courtesy of Winvian Farm

Situated a short walk from the main building, the spa occupies 5,000 square feet of space. After arriving and changing into the provided terrycloth robes, we were immersed in tranquil music and a white-out of drapes, fluffy rugs, pillows, blankets, and oversized couches, which we nestled into while sipping tea. I traded my attention between my favorite book and the view through the big floor-to-ceiling windows overlooking the resort’s grounds and water fountains.

A couple's massage at the spa. Courtesy of Winvian Farm

While I was relaxing in the common area, my wife opted for the Winvian Ultimate Facial from the diverse spa menu. The treatment was performed by the spa’s director, Lauren, and included deep exfoliation, oxygen infusion, cryotherapy, and other techniques that Lauren has mastered. A face, neck, shoulder, and hand massage were also a part of the 90-minute treatment. It was a true indulgence, and well justified to mark our important milestone. My gift was seeing the glow and sense of inner and outer rejuvenation emanating from my wife’s face following the treatment.

Spa director Lauren expertly provides a guest with a facial. Courtesy of Winvian

As we were getting set to depart, I had a moment to reflect on our time at Winvian.

While speaking with Ms. Smith, she shared her pride in the staff and their long tenure, and how the intimate size of the resort lends to a very personal experience.

“It’s a sweet spot ... where it feels like a family. We are an extension of my home,” she said.

When You Go:

Getting There: Winvian is a two-hour drive from New York City and 2.45 hours from Boston.

Reservations: For information and booking cottages, dining, and spa, visit Winvian.com

The author was a guest of Winvian Farm.