Home Away from Home

The INN at Ormsby Hill is a retreat for travelers coming to Manchester that offers a unique, historical experience in what feels like the comfort of your own home 

STORY BY MEGAN DEMAREST 

PHOTOGRAPHY BY CRAIG LIGHT & 

COURTESY THE INN AT ORMSBY HILL 

Imust have driven by the property a hundred times during my journeys north on Route 7A through Manchester. Each time, I admired the stone wall and the painted sign, turning my gaze ever slightly to keep it in my view as I passed. It seemed like a welcoming place to step back in time. Settled on a gentle slope, the INN at Ormsby Hill holds over 250 years of Vermont heritage inside its walls, including its namesake, Revolutionary War hero, Gideon Ormsby. Constructed in 1764 by Thompson Purdy, the building ranks among the oldest in the community, and much has been written about its history. It changed ownership multiple times before entering its most notable period in 1885, marked by the arrival of Edward Swift Isham.

Maryann and Jack Orlando celebrate a decade of stewardship.

Isham was a prominent Chicago attorney, a Vermont native, and the law partner of Robert Todd Lincoln, the only surviving son of President Abraham Lincoln. He transformed the old Purdy farmstead into a grand summer estate, working with architect F.W. Stickney to add a tower, verandas, greenhouses, and a sugarhouse for maple syrup production. The estate quickly became one of Southern Vermont’s most elegant retreats, welcoming distinguished guests including President William Howard Taft and Mrs. Ulysses S. Grant.

Robert Todd Lincoln, Abraham Lincoln’s son, was a regular visitor — and he loved Manchester so much he tried to convince his friend to sell him a piece of the hill. The story, still told with delight today, is that Isham famously refused: “You’re my best friend and law partner; you’re NOT going to be my next-door neighbor.” After Isham’s death in 1902, Lincoln was able to acquire the land behind Ormsby Hill, where he built Hildene — now one of Vermont’s most visited historic sites. The two estates remain linked to this day, neighbors in both history and spirit.

After decades as a charitable foundation serving underprivileged boys from New York City, Ormsby Hill was converted into a bed and breakfast in 1987. It has earned the AAA Four-Diamond Award every year since 2000 and is listed on the National Historic Register. You can read more historical details on the INN’s website, streamlined by its current proprietors, Maryann and Jack Orlando. The Orlandos have remained true to the historical vision of this welcoming bed and breakfast since 2016, and in that time, they have changed remarkably little — which is, it turns out, exactly the point. What they have done is cared for a house full of storied history, and made it feel like home. 

Stewardship 

I was delighted to finally have an opportunity to see the interior of this impressive estate and congratulate its innkeepers on 10 years of stewardship. Jack, a native New Yorker, spent decades in accounting and finance. Maryann hails from Connecticut, her vision shaped by years in interior design and visual merchandising. How did they come to find themselves running a 10-room historic inn in the Green Mountains? Spend five minutes with them and the answer becomes clear. 

The seed was planted by Maryann’s brother and sister-in-law, who had spent ten years running an inn of their own. “We were familiar with the business,” she explains. “We didn’t just pull it out of a hat.” For about five years, the couple searched the region for the right property — one that matched both their instincts and their standards and had come up short. When the INN at Ormsby Hill became available, Jack declared, “This is it. If this doesn’t work, we’re done.” By all accounts, it’s safe to say that it worked. “It all fell into place and here we are,” adds Maryann. 

Initially, what drew them to buying an inn wasn’t just finding the right property — it was the idea of doing something together as a couple. “We spent our life going in different directions,” Jack recalls. “She had to drive somewhere, I had to drive there separately, and then we had to drive home alone. This is something we can do together.” Ten years in, he laughs, “we’re getting the hang of it.” 

They had also planned for it to be their retirement. Maryann will be the first to tell you it isn’t — not exactly. “I always say to him, I hope there’s another retirement after this that doesn’t involve lots of work.” The inn runs seven days a week, and there’s always something needing attention: a repair, a room to repaint, a tradesperson at the door, a curious traveler who has driven by for years and finally stopped in (like me). “It’s a big house,” Jack says simply. “That means a lot of work.” 

But both speak about their decade here with pride and fondness, not overload or exhaustion. What surprised them most, they say, was never the workload — it was the guests. “The best thing we never anticipated, no one ever told us, was the enjoyment we’d get out of our guests,” Jack shares. “It’s the nicest part about this business. People come because they want to have a good time. They’re enjoyable to be with.” 

Since 2016, Jack and Maryann have thought of themselves not as owners, but as stewards. “We’ve got to maintain the integrity of what this property was,” Jack says. “Those who did this prior to us, over the years, kept to that. We didn’t want to make radical changes. We just felt it was the right thing to do.” Over their fifty years of marriage, they’ve worked as a team, ensuring almost nothing slips through the cracks, including the inn’s heritage. 

The INN 

The INN at Ormsby Hill is the kind of place where you can slow down and take in all the glorious details at your leisure. The main structure is an architectural study in New England character. Over the years, wings and additions have layered onto the original frame, always with an eye toward authenticity. 

Inside are ten guest rooms, each one unique. No two are alike in layout, proportion, or personality, and that is part of the inn’s appeal. Returning guests often request the same room visit after visit, having claimed it as their own. Others make a point of trying something different each time, working their way through the house to experience the distinct character of each space. Together, the rooms can accommodate up to 23 guests, though the inn doesn’t feel crowded — the spaces are generous with plenty of privacy. 

The Robert Todd Lincoln Room features a jacuzzi tub fitted with sliding doors that open directly into the main room, so guests can soak while enjoying the fireplace or watching television, depending on their mood. The Francis Suite offers the special luxury of two full bathrooms. Each room at the inn has its own private bath, its own character, its own atmosphere. 

The library draws guests in and keeps them there. Shelves of rare and antique books line the walls, creating a collection that encourages leisurely browsing, perhaps by the fireside during the colder months. Nearby, the dining room reveals its own history: along the upper shelves sits a set of Indian Tree china — a pattern prominent in its day — that illustrates the direct connection between the inn and Hildene. It’s the same china used in the Pullman rail cars, like the Sunbeam, which can be found on the grounds of Hildene. The only difference between this china and the set used aboard Sunbeam, Jack notes, is a small filigree detail that reads “Pullman” on one and not the other. 

One sweet addition that the Orlandos added is the small gift shop near the entrance, which sells beautifully crafted INN at Ormsby Hill mugs, Mocha Joe’s coffee, wine, and, of course, local maple syrup. 

Outside, the grounds extend the experience. Jack tends the garden himself — roses, peonies lining the property, and beds that bloom in spring. A slate patio and a gazebo offer places to sit and relax, which is exactly what many guests are looking for. “I do the work,” Jack says of the garden, with a nod and a smile to Maryann. “She supervises.” 

The whole property is maintained with a great deal of care. Maryann’s background in interior design shows in the coherence of each room — the 18th-century aesthetic held consistently throughout, repainted and refreshed over the years but never abandoned. “We would never veer from that,” she says. While there have been mechanical and technological updates, the feeling of the place and time remain deliberately unchanged. 

It is, in the end, a house that has been many things to many people over the centuries. The Orlandos are humbly its latest and faithful keepers. 

The Guest Experience 

From the moment guests arrive at the INN at Ormsby Hill, they know they are in for a personalized experience. There is no typical front desk transaction or key card slid across a counter. Jack and Maryann greet every guest face to face and make sure they feel settled before stepping away. “One of the most important things when people walk through the door is we greet them and we sit and talk with them, so they feel comfortable,” Maryann explains. “We don’t just stand at a desk and say, ‘here’s your key.’” 

That attentiveness carries through the entire stay. At breakfast, which receives consistent positive reviews, Jack takes orders tableside and returns not just with food, but with questions— was the room comfortable? Is this your first time in Manchester? “If you don’t ask, sometimes they won’t say,” he notes. Maryann, meanwhile, loves curating a day for guests who want guidance: a scenic drive, a garden to visit, a trail worth taking. And when they return in the afternoon, she wants to hear all about it. “I like to find out— how did it go, what’d you think? Usually people love to talk, and it’s fun to hear their responses.” 

The result is a guest book filled with the kind of entries that are hard to manufacture. The book itself came into being at a guest’s urging — the Orlandos hadn’t started one in their first year, and then a guest presented one as a gift and wrote the first entry. They’ve had one ever since. “It’s very heartwarming when I read through them,” says Maryann. “People write really lovely things.” 

Some of those entries mark joyful occasions — weddings, anniversaries, family reunions, graduations. Guests who were married in Manchester return year after year to celebrate where it all began. Others carry heavier stories. One couple came knowing it would be the wife’s last trip; she was dying of cancer. Another husband brought his wife, who had Alzheimer’s, back to a place they had loved together, hoping the familiar surroundings might offer some comfort. When they pulled through the gates, she recognized them and began to cry. 

The Orlandos hold these stories carefully. They understand that for many guests, a stay here is not incidental — it is the trip, one that marks a milestone occasion. And they treat it accordingly. 

What keeps people coming back — some for 25 years running— is harder to name than any amenity. It has something to do with pace and comfort. “People sit, relax, talk, and make friends here,” says Maryann. “You’re not just visiting— you’re staying home.” Her guests seem to agree. Some walk through the door and say so: We’re home. 

“I’m very humbled by that,” she says. “It’s special. And that’s what Jack and I have strived to do — make people feel happy and comfortable and want to come back.” 

These are not the stories of a hotel. They are the stories of a home — one that happens to have ten rooms, a saltbox roof, and two people at the door who genuinely want to know how your day went. 

For visitors who want to experience a part of the soul of Manchester, the INN at Ormsby Hill is an ideal place to begin. And if the Orlandos have anything to say about it, an even better place to return. 

ormsbyhill.com