Welcome home to Hillholm.
HILLHOLM, named by and built for Amos G. Winter, is a stately turn-of-the-century Georgian Revival mansion overlooking the rural village of Kingfield, nestled in the foothills of Maine’s western mountains. Formerly known as the beloved Inn on Winter’s Hill, Hillholm houses Santosha, our yoga and mindfulness retreat center, and From the Fishouse, a not-for-profit organization dedicated to supporting emerging writers through publication opportunities and residencies as they hone their craft.
Freeland and Francis Stanley, born in Kingfield in 1849 and renowned for their invention of the Stanley Steamer automobile, were close friends of Amos G. Winter. Winter was a wealthy grain merchant born in Kingfield who introduced the first delivery wagon system in the region. By 1884, Winter was operating Winter’s Store at the base of Winter’s Hill, selling everything from groceries to hardware. As the story goes, upon returning from a hunting expedition, Freeland asked Winter if he had anything planned for the afternoon, and when Winter answered in the negative, Freeland jovially said, “Let’s build a house on the hill.” They set to designing it informally, and soon, the Stanley brothers returned to Boston to draft formal plans.
The brothers’ timing was apt. In a bid to woo Julia Magdalena Roesch, a New York socialite, to marry him, Amos G. Winter set out to build a suitable estate with modern amenities. Familiar with the Stanleys’ trendy house outside Boston (165 Hunnewell Avenue, Newton), Winter asked them to build the same home, but with an expanded footprint.
CONCEPT
The Stanley brothers were considered engineering geniuses of their day. They planted a full-sized railroad boiler in the cellar to pump steam through a series of immense radiators in the house, making the mansion the first private home with central heating in the State of Maine. They also designed a steam-driven elevator in the home which was never finished.
The mansion’s ornate décor included, among other things, a Chickering box grand piano shipped by horse-drawn wagon over two full months from Boston in 1872, making it the first piano in Kingfield. That same piano still sits in one of the sumptuous salons. The floors of the mansion are original, made with timber felled from the property itself. At the top of the elaborate staircase leading up from the Grand Salon, Julia Winter installed a tall palm brought from California by Amos’ grandmother. Smooth Italian plaster ceilings were new and expensive at the time; after adding them, though, the plaster remained soft and collapsed into the house a day after installation, requiring Winter to revert to customary hammered tin ceilings, most of which are still intact today. Adjacent to the home sat a ninety-foot barn just a stone’s throw from the mansion; it housed cattle, oxen, and horses, but was torn down by 1930.
Amos G. Winter died in 1920, although his three sons continued to live on site with their wives and families until the house became too crowded. By 1950, the entire extended family had moved away except Amos G. Winter Jr. and his wife, Alice. Considering the estate’s upkeep impractical, Amos and Alice sold the property to Dr. Stanley Covert in 1950 and moved into a small trailer at the edge of the estate’s front lawn. Amos G. Winter Jr. is now famous in his own right as the founder of Sugarloaf Mountain Resort. In 1950, he cut the first trails up Sugarloaf Mountain with a group of friends fondly known as the Bigelow Boys. The group leased the northern aspect of the mountain from the Great Northern Paper Company. In 1951, Winter’s Way, dropping 1,800 feet from the summit snow fields, saw its first skiers, with Amos G. Winter Jr. out front. Sugarloaf’s signature summit snow fields are the only lift-serviced above-treeline terrain in the East.
CONSTRUCTION
Dr. Stanley Covert converted the estate into a rural hospital, adding a one-story wing to the mansion’s eastern face, which housed examination rooms and X-ray equipment, now our craft cocktail bar. Dr. Covert’s father built an apartment where the original barn sat, with the medical wing connecting it to the main house. As the sole practitioner in the area, Covert charged three dollars for office calls, four dollars for house calls, and twenty-five dollars for deliveries. Dr. Covert also became infamous locally for keeping two bear cubs, named Amos and Andrea, in a pit in the back yard of the property, which some locals still remember from childhood. Dr. Covert owned the estate until 1967 when he left Kingfield.
The property fell into major disrepair until Michael Thom, an architect from Cambridge, MA purchased the property in 1972. Thom made meaningful changes to the property, including restoring damaged interior elements; adding an outdoor swimming pool; restoring the clay tennis courts; replacing the original steam furnace installed by the Stanley brothers; and opening a fine dining restaurant. Thom named the restaurant Le Papillon and served French haute cuisine, like escargots and steak au poivre vert. He created a membership-only Winter’s Inn Pool and Racquet Club, offering Sunday champagne tournaments. Folks in town still remember his extravagant poolside Gatsby-themed parties. He converted Covert’s attached apartment building into guest rooms and a bar called Balthazar’s Pub, known for its live music and rowdy parties; he named it after his cat. During one such party, the barn caught fire—supposedly when someone flicked a joint onto the floor—and the whole building burned down.
In 1989, Richard and Diane Winnick purchased the property out of bankruptcy and began their own rehabilitation of the property. They modernized the commercial kitchen and added an indoor swimming pool (since removed) to the rear of the building. Folks who grew up in the area remember taking swimming lessons in that pool as children. They rebuilt the barn and converted the entire space into sixteen spacious guest rooms across three floors. They, too, opened a French restaurant called Julia’s in the dining rooms.
IN WINTER’S WAKE
In 2015, John E. Banta purchased the Inn on Winter’s Hill from Richard and Diane Winnick, appending 23 Winter Hill Street, the adjacent lot containing the trailer in which Amos and Alice Winter lived. Banta, originally from Kennebunkport where his family ran the The Colony Hotel, a 1914 seaside resort, also spent his career in hotel management, having graduated from Cornell University with a BS in Hotel Administration and spending his entire career managing Hyatt Hotels and Miyako Hotels and Resorts in Japan. Perhaps John’s greatest accomplishment, though, was his connection to the community. He is much beloved by everyone for the cozy atmosphere he created with his wife, Vivian; his unbeatable burgers and pub fries; and his unique addition of Tuesday night karaoke which, unlikely as it may seem in these hallowed halls, brings the community together, week after week, in joy.
THE LAST DECADE
And so we succeed this long line of stewards of one of Maine’s most iconic great houses. Elsewhere in the United States, even in Maine, estates of this grandeur existed far before the turn of the nineteenth century. Maine’s wild western mountains were slower to settle, more rugged to access. Fitting, then, that as the world spins ever faster outside these mountains, we practice slowness within them.
JennyBess Chaim originally hails from Massachusetts and spent every summer in a rustic hunting camp on China Lake in Maine, paddling, fishing, and learning the great joys of frigid Maine waters. More recently, JB has called Phippsburg home. An attorney, JB left her practice several years ago to live more meaningfully; she remains a mediator in Maine. Her travels took her all over the world, especially by boat, as she kitted out a sloop and sailed across the Atlantic Ocean. She returned to Maine to create a mindfulness retreat in rural Phippsburg. She is also pursuing her Master of Divinity at Harvard Divinity School (MDiv ‘26), studying meditative states and psychedelic experiences. Thanks to this incredible community of business owners and neighbors in Kingfield, JennyBess already feels right at home in the mountains. She’s thrilled to feed you delicious nosh and see you gather once more in these great, warm halls.
Born and raised in Maine, Matt O’Donnell graduated from Holy Cross and earned an MFA in creative writing from the University of North Carolina at Greensboro. In 2004, he and Camille Dungy founded From the Fishouse, a non-profit audio archive of emerging poets that focuses on the oral tradition of poetry. A former collegiate rower and football player, Matt became an avid runner and cyclist. He has a thirty-four-year coaching background as a ski instructor that began at Sugarloaf and his family’s A-frame in Carrabassett Valley. Matt recently retired from Bowdoin College, where he was editor of Bowdoin Magazine, and where he directed a telemark ski program for the Bowdoin Outing Club. He holds PSIA Level 3 certification in alpine and telemark skiing, is a PMBIA-certified mountain bike instructor, a certified Spinning instructor, and an RYT-300 in training. Matt’s great uncle, Bob, was an early Sugarloafer and friends with Amos and Alice Winter, and Matt’s father, Tim, remembers visiting the Winters at Hillholm as a boy.
We’d be honored to join you for a pint, some afternoon tea, or a stroll down to the river. If you have any fond memories of your time at Winter’s Hill or can share recollections about the history of Hillholm, we’d love to hear from you: you can reach us at hello@santosha.org.
HILLHOLM TODAY
