Chauncey Stillman’s Equestrian Estate

Outside Millbrook, New York, sits a grand estate known as Wethersfield. An archetype of elegance and environmentalism, combining stunning Italianate gardens, stables, and soil and water conservation, the estate serves as the manifestation of the vision of one extraordinary man.

Chauncey Stillman was born in 1907, a grandson of James Jewett Stillman, who headed the bank that would grow to become Citigroup Inc. He attended Groton and Kent, entered the Harvard College Class of 1929, and received a degree in architecture from Columbia University. In 1939, he married Theodora Moran Jay; together, they had two daughters.

Chauncey Stillman with his daughters.

Stillman was a horseman, a yachtsman, an art collector, and a conservationist. He served as commodore of the New York Yacht Club from 1964 to 1966, and merged his other interests by establishing Wethersfield, which he formed by combining adjoining former dairy farms in the late 1930s, and added to over the following years with adjacent properties as they became available. The resulting estate comprises 1,200 acres of formal gardens, stables, and carriage trails, all overlooked by a Georgian-style brick mansion filled with great works of art.

Stillman atop Gonaway, a horse he praised as “my greatest hunter,” 1939.

In the 1960s, Stillman, who had long ridden with the Millbrook Hunt, began instead to cultivate an interest in carriage driving. He built a carriage house in the courtyard of his stable to hold his growing collection of vintage carriages (over the years, he acquired and restored 22 of them, dating from 1850 to 1910), and kept a stable full of Hackney horses to drive them. Stillman and his team competed at events including the Devon Horse Show and the Royal Toronto Winter Fair, and also hosted several carriage driving events at Wethersfield. His house guests there were treated to daily afternoon carriage rides on the approximately 20 miles of carriage trails on the estate.

Stillman and one of his granddaughters out for a carriage ride.

Equestrian pursuits remained a lifelong interest for Stillman. As he wrote in the Harvard University Class of 1929’s 50th Anniversary Report: “I have long since given up fox-hunting, and more recently, yachting—not in deliberate renouncement, but in neglect of each opportunity as it arose until eventually a negative habit pattern emerged. No longer do I feel impelled to enter horses in competition, exhibitions, and coaching marathons, as I have done until recently. But I still enjoy the leisurely riding and driving of horses (mine are large creatures of the Hackney breed).”

Following Stillman’s death in 1989, Wethersfield is now overseen by a foundation and is open to visitors, and his carriage-driving tradition continues there today.

Stillman and guests out for a ride.