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Inn Vermont: Four Chimneys Inn

Updated: Mar 22, 2022



In a quiet and bucolic clearing on West Road in the historic district of Old Bennington, a charming and sophisticated sanctuary beckons discerning travelers in search of a remarkable and restful retreat. The Four Chimneys Inn has a rich and storied past, and its future is looking brighter than ever. Current owners Lynn and Pete Green work diligently on a daily basis to create an oasis of countrified tranquility that gracefully preserves its legacy, providing exemplary service for guests of all tastes and preferences. Integrating old-world aesthetic sensibilities with contemporary comforts, they offer an elegant lodging experience that is both unique and memorable.

The Four Chimneys Inn was first built in 1783. Originally, it served as the residence of Reverend David Avery, the second pastor of Bennington’s Old First Church. Due to the fact that Reverend Avery was unable to manage the upkeep of the property, he eventually sold it to Nathaniel Brush, a local politician who had nobly fought in the Battle of Bennington. After Brush fell on hard times, he converted the property into a boarding house in the early 19th century. In 1870, the boarding house was purchased by a Troy, New York-based businessman named Tom Saxton, who restored the property to its original state. After a tragic fire burned the mansion down to its foundation in 1910, Philip Jennings acquired the estate. He then rebuilt it from the ground up with the help of renowned architects Lewis Colt Abro and Harry T. Lindeberg. During the course of Jennings’ ambitious restoration project, he built two additional outbuildings behind the property: a carriage house and an ice house. Today, these buildings now house two beautiful guestrooms.

In 1949, the property was sold to James Rollis, who opened a fine dining restaurant that hosted Hollywood starlets and magnates such as Elizabeth Taylor and Walt Disney. Several decades later— in the early 1990s— the restaurant was acquired by Alex Cox. While Cox continued to oversee the restaurant, he also converted the property into an inn, fixed up the outbuildings, and renovated several of the guestrooms. In 2005, the Four Chimneys Inn was purchased by its current owners, Lynn and Pete Green. Before they left their corporate jobs in Boston behind to move to Vermont, Lynn spent years working in the field of marketing, and Pete worked as an engineering manager. Lynn Green says that after making the decision to relocate to Vermont, she and Pete began to research potential inns that were for sale. When the Greens came across the Four Chimneys Inn, they were instantly smitten with its charming ambience. “When we were working in Boston and decided that we wanted to move to Vermont and manage an inn, we originally thought it would take us about five years to find the right inn. When we saw the Four Chimneys, we fell in love almost immediately. We knew that we had to accelerate our timeline, so we put in an offer.”

Although the inn was initially under contract with another buyer, the sale didn’t end up going as planned. “We told the former owners to notify us if anything changed,” says Green. “Six months later, they called us up and told us that the sale hadn’t gone through. They ended up doing the sale with us, and we’ve been taking care of the inn ever since.”

Before the Greens relocated to Bennington, they decided to get married at the inn before the transition of ownership had officially processed. “We were planning to get married already, and we knew that we wouldn’t have time for the wedding after we bought the inn. We had a small wedding there, and it was a wonderful experience.”

After the Greens moved to Bennington, they redecorated the inn and enhanced its atmosphere through a series of small improvement projects. “We didn’t knock down any walls, but we freshened up the décor throughout the inn and replaced all of the furniture. There were a lot of fun surprises along the way that we weren’t expecting. We pulled up the carpet in the patio dining room and found some gorgeous herringbone brick floors underneath. We also found beautiful original wood floors underneath the carpet in the main dining room. In some places, there were thick original moldings that we really loved, so we kept those. We added new molding in other places, put in heat pumps, and put in new roofs, but we didn’t do too much more in terms of construction. We wanted to preserve the original charm of the inn. When I redid the bathrooms, I kept many of the original antique pedestal sinks. The rooms are a nice mix of modern comfort and rustic nostalgia, which creates an inviting and relaxing mood for our guests.”

The Four Chimneys Inn houses eleven different guestrooms, each of which possesses its own special charm. On the first floor, a large, stately room with a king-sized bed and additional four-poster mahogany bed offers breathtaking outdoor views from its private glassed-in porch. The king-sized bed’s headboard is made out of a repurposed door from an old shed that once stood on the property. A second room on the first floor with large bay windows offers fantastic views of the sweeping front lawns and nearby Mount Anthony. The room also features a heated private glass porch, a plush and comfortable love seat, a gas fireplace, and a marble-topped vanity in the bathroom.

On the second floor, a spacious guestroom with hardwood floors overlooks the south lawn and a 150-year-old stone wall. The bathroom is outfitted with marble and tile floors, a large jetted tub and an enchanting chandelier. “This room is a favorite of honeymooning couples,” says Green. “It has a very romantic ambience.” Down the hall, another inviting guestroom boasts a wood fireplace and newly-refurbished wood floors. The bathroom features white wainscoting, Ralph Lauren printed floral wallpaper and a marble two-person shower. Further up on the third floor, a room with European-style windows and sloping ceiling eaves overlooks the front lawns. This cozy and secluded room provides an intimate escape for visiting vacationers. The newly-tiled bathroom is enhanced by an antique pedestal sink, as well as delightful retro-chic wallpaper.

The Carriage House and Ice House each offer splendid accommodations. The Carriage House has a sunny and cozy feel, with framed floral artworks hung over the bed and a newly-renovated bathroom with miniature Carrara marble subway tile floors. The Ice House features two-levels with a spiral staircase, brick walls, gas fireplace, and an upstairs loft. It serves as an ideal refuge for small families and honeymooners.

Throughout the inn, the walls are lined with several historic artifacts, such as a print of a Norman Rockwell painting set in front of one of the Four Chimneys Inn’s original fireplaces. In addition, a framed landscape and garden design by renowned landscape architect Ellen Biddle Shipman is prominently displayed in the front staircase. Shipman was commissioned to design an outdoor garden by Philip Jennings in the early 20th century. Her design for the garden at the Four Chimneys estate features her signature axial layout. Today, the Four Chimneys Inn grounds feature a beautiful outdoor flower garden, a stone courtyard with a fountain, and several tall, majestic trees. “People love walking around outside, regardless of what time of year it is,” says Green. “Every season in Vermont has its own form of beauty.”

Green says that one of the best things about owning the Four Chimneys Inn is hearing the stories of her recurrent guests. “Over the years, people have sent us photos, postcards, and artifacts. One guest sent us an article about when James Rollis’ restaurant first opened in the 1950s. When we first bought the inn, a man came up the steps and told me about when he and his wife came to eat dinner at the Four Chimneys Inn on their wedding night three decades earlier. He told me that they stayed somewhere else that night because they were young newlyweds, but that he had finally worked up the nerve to ask me how much a room was. It was an incredibly cute moment that really drove home just how much this place really means to the guests that come here.”

Another one of Green’s favorite stories involves a couple that came to visit the inn with their three daughters. “When they first came in, they told me a story about when she had a medical incident several months earlier in the middle of the night. When the ambulance came to her home, she said ‘Oh, Lord, don’t take me now! I’m going to The Four Chimneys in May!’ They had the best time when they stayed here and they were such a sweet family. Whenever they came to breakfast, they would always joke about needing an endless supply of maple syrup. That story makes me smile every time I think of it.”

Although the Four Chimneys Inn no longer serves lunch or dinner, Lynn Green does cook and serve delicious breakfast staples every morning, such as blueberry French Toast and buttermilk pancakes. Lynn and Pete Green also go above and beyond to provide their guests with attentive and considerate service that allows them to enjoy their Southern Vermont vacation in the way that they want to. “Everyone comes to The Four Chimneys with a different experience in mind. We like to let our guests set the tone for their visit and give them all the space that they need to enjoy their time here on their own terms. Old Bennington has a very grand and elevated atmosphere, but we want to provide an experience that is elegant without pretense. Our aim is to be as welcoming as possible and make people feel like they’re at home here. I’ve had some of the happiest moments of my life here at The Four Chimneys. I’ve gotten married here, had our child here, and I’ve had the chance to connect with some amazing people – including our returning guests who have chosen to make The Four Chimneys a big part of their lives. Whether you’re coming here to get engaged, coming here to get away, or coming to visit your family for the holidays, we want to help you experience similar moments of joy and make happy memories that stay with you for the rest of your life.”

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