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So Many Marvelous Middleburg Memories for Nattie Kaye
So Many Marvelous Middleburg Memories for Nattie Kaye
By Leonard Shapiro
Nathalie Hazard Kaye, known to one and all in these parts simply as “Nattie,” will celebrate her 100th birthday in October. She arrived in Middleburg when she was eight and is the oldest living graduate of The Hill School, though conditions when she started in the fourth grade were not quite the same as the Class of 2024 ever experienced.
She was born in New York City and spent her early childhood living on Long Island until her parents divorced when she was eight. At that point, Nattie admitted recently she was “scared to death” about moving, with so many sudden changes in her young life. Nevertheless, she headed south with her mother, an avid rider to hounds who had visited the Middleburg area several times and loved all it had to offer, particularly its equine opportunities.
At that point, Hill School, founded in 1926, no longer was conducting classes in what eventually became a bank building and now houses the King Street Oyster Bar. By 1936, the school had moved to a small building where the far more expansive current campus is located.
“We had two teachers, Miss (Anita) Thomas and Miss (Willie) James, who actually ran the school,” Nattie recalled. “Some of the parents had spoken with Mr. Buckley of the Buckley School in New York City and he helped them organize it and found the two teachers. There were 15 kids in the whole school.”
From Hill, it was on to boarding school in Massachusetts and a year of college at Sarah Lawrence. “and then there was the war,” she said, as in the start of World War II. Nattie volunteered with the Red Cross as a nurse’s aide based at the Ashford Hospital in White Sulphur Springs, West Virginia (now the Greenbrier Hotel). One weekend, she came home to Middleburg to attend a New Year’s Eve party held at a local school, and that night met Howard Kaye, who lived in the area.
She was 20 years old when they married, with another horsey connection in the mix. Howard’s mother had married Jack Skinner, a well-known Middleburg horse trainer who also had a working relationship with Hirsch Jacobs, a Hall of Fame New York trainer. Jacobs often sent his horses down to Skinner in Virginia for some rest and relaxation. And Nattie, a fine rider herself, frequently galloped those horses out in the field.
Like her mother, Nattie also was an avid foxhunter and rode with the Middleburg, Piedmont and Orange County hunts. Howard Kaye, who preferred golf, nevertheless ended up running the Middleburg Training Track for many years when it was founded and owned by Paul Mellon. Howard Kaye passed away in 2006.
The Kayes also were among the first members of the then fledgling Middleburg Tennis Club in the early 1960s. Nattie eventually gave up riding when the second of her three sons was born, but played tennis and golf for many years. The three boys, Howard Jr., Woody and Billy, all were Hill School graduates, of course.
“There were about ten families and we all had little kids and we wanted them to learn how to play tennis,” Nattie recalled. “Molly and Charlie Morgan’s parents (Pat and Annie Morgan) had the property and Jack Skinner’s stable had been near there too. We had two courts, and Polly Dudley was the first tennis pro. Then it was Morgan Dennis. He had been captain of his boarding school tennis team and he was hired and never left.”
Nattie began her own long working career when she joined Middleburg Real Estate, then owned by Bud Morency. She eventually bought him out and ran the firm for more than 25 years, with some rather interesting clients, to say the least.
She sold Abe and Irene Pollin their Middleburg home when Abe Pollin owned the Washington Bullets/Wizards NBA franchise. She sold author Herman Wouk (The Caine Mutiny, which won a Pulitzer Prize; The Winds of War and War and Remembrance) his Middleburg house.
She also showed property in the area to a brash boxer named Muhammad Ali. “He had a whole bunch of henchmen around him,” she described Ali’s hangeron entourage, “and they all wanted him to buy so they’d have a place to live. But I don’t think he had much interest in it.”
Nattie had both great interest and great success in the real estate business. “It was fun,” she said. “I knew most of the farms and the owners around here, and I had a lot of listings.”
She eventually sold her firm to one of her agents, Chris Malone, but actually came out of retirement at age 88 to show and sell properties for her friends Gloria Armfield and the late Ruth Miller, who had started their own real estate business.
These days, Nattie Kaye is living in the same house she’s occupied for 55 years. It backs up to the Glenwood Park steeplechase racing course, where she and Howard often invited friends on race days to join them for their own private tailgates about as close to the action as possible.
She’s also been a huge fan of author Dick Francis and his racing related mysteries, which is exactly what one might expect from one of horse-crazy Middleburg’s most iconic and delightful residents.
