The Simpson Family in front of the farmhouse1860's - which later became the Lodge Ben Thurber's Rendering of a snowy Lodge1982 Judy Dales's quilt of Lodge History hangs in our front hall The Smith Family Holiday Cardc.1955 Three Generations of the Smith Familywho ran the Lodge for over 60 years

History of Highland Lodge


"I wonder if I have ever felt more alive, more competent in my mind and more at ease with myself and my world, than I feel for a few minutes on the shoulder of that known hill, while I watch the sun climb powerfully and confidently and see below me the unchanged village, the lake like a pool of mercury, the varying greens of hayfields and meadows and sugarbush and black spruce woods, all of it lifting and warming as the stretched shadows shorten." - Wallace Stegner


To understand why so many guests return year after year, generation after generation to this lakeside retreat, it helps to learn a little about the history of Highland Lodge, the town of Greensboro, and the geography of this wild, remote corner of Vermont known as the Northeast Kingdom.

Highland Lodge sits on one hundred and thirty-two acres on Caspian Lake and Barr Hill in Greensboro, Vermont. "The Northeast Kingdom", or "NEK" was a name given to the state’s three northeastern-most counties by former Vermont Governor (and U.S. Senator) George D. Aiken, who was moved by the beauty of the area. It is arguably the most fiercely independent part of Vermont, as well as it's poorest economically. The terrain varies tremendously, from swampy bogs flanked by dark pine forests, to deep and cold fjord-like lakes, rolling mountains and hillside pastures, flanked by majestic stands of maples.

There are many picturesque places in The Kingdom: Lake Willoughby, Island Pond, Jay Peak...but none has captured the imagination of writers and artists as intensely as the town of Greensboro, a summer refuge for creative types since the late 1800s. One of the most noted of these artists was Wallace Stegner, the Pulitzer-Prize winner who set his novel, "Crossing to Safety," in a town modeled on Greensboro. In the novel is a brief nod to the development of what is now a treasured mainstay of the community, Highland Lodge.

Perhaps it's fitting that the name "Highland Lodge" is also part of a creative myth, as the main “Lodge” is not really a lodge at all – it was a farmhouse built in the 1860s by the Simpson family. Later the Goodrich family owned it and sold it to developers in 1926. These developers created the name and planned to build over seventy cabins, christening the main house as the ‘Lodge’. They had only built the kitchen wing of the main house, four little cabins, and sold some parcels of land before the stock market crashed in 1929 and the rest of their grand development scheme was abandoned.

Nevertheless, Highland Lodge was born in the 1920s and survived the Depression and WWII years as a boarding house run by one of the founders, John Barrington. Then in the rainy summer of 1954, an energetic, vacationing family of ten - sisters Carol Smith and Narcissa Boyd, together with their children, mother, and Carol's husband Dave Smith - took to the notion of buying the lodge one night at dinner, and in a matter of weeks, it was theirs. The property was to thrive in the same family for over sixty years.

Over the course of the 20th century, Greensboro became a coveted place to enjoy summer vacations, with many professors from Yale and Princeton bringing their whole families up to summer on Caspian Lake. Highland Lodge became a fixture of the community as both a source of lodging and as a community gathering space. The Smiths renovated and added rooms, built the Ski Hut, additional cabins, a game room, raised the roof, and added an additional dining room which is now our House Bar.

In 1979, Carol and Dave Smith, Sr, sold the property to their son, David Smith and his wife, Wilhelmina. David and “Willie” decided to cut ski trails through their forest land and worked with their neighbors to develop a world-class trail network. This allowed the Lodge to remain open year-round for winter recreation in addition to the beautiful summer season. Today this trail network connects with the famous Craftsbury Outdoor Center trails, and the COC grooms and maintains the trails here in Greensboro to offer an unparalleled selection of picturesque Nordic skiing.

By 2015, the Smiths had listed Highland Lodge's property for sale, and a few families from the Upper Valley who loved visiting the lodge considered a purchase. In the summer of 2016, they teamed up with entrepreneur Heidi Lauren Duke to invest in the property and revive it as a classic New England bed and breakfast. Ms. Duke oversaw the revitalization of Highland Lodge for the next three years, adding a House Bar and some necessary strurctural improvement to this historic building before passing the torch onto current management. With a decade long background in Hospitality Management and a passion for the outdoors, present General Managers, Elsa Schultz and Chad Sims, have been working diligently to maintain the historic charm of the Highland Lodge and are looking forward to continuing to preserve it's sterling reputation.  

Learn more about the Highland Lodge as an enduring destination in Seven Days "Stay Tripper" 2020 article. 

Learn more about Peter Milliken and other ownerstransition in this article in Seven Days, Vermont's statewide paper. 

Learn more about "Vermont's Flavor Empire" in American Way's national magazine spread, featuring Highland Lodge and many other gems of the Northeast Kingdom.