During World War II, Harry served as a transport pilot in the U.S. Air Force, where he flew search and rescue operations throughout Europe, Asia, and the Pacific — ferrying wounded troops back home from the front.
Harry during World War II
In 1947, he married Kate de Forest Jennings, a daughter of Kate de Forest Prentice and Brewster Jennings, who was the chief executive of the Mobil Oil Corporation from 1944 until his retirement in 1958.
Harry and Kate’s wedding day — March 1, 1947
Harry and Kate spent the first few years of their marriage living in a private apartment at the southern end of The Brick House in Shelburne, which was home to Harry’s parents, Electra and “Watson.”
In 1948, Electra and Watson gave Harry and Kate the land that would become High Acres Farm, to establish a home for their nascent family.
Harry and Kate in Shelburne — late 1940s
They had three daughters together: Kate Brewster (born in 1948), Laura Havemeyer (born in 1950), and Dundeen Cromwell (born in 1952).
Harry and Kate with their daughters — mid 1950s
In 1952, when the Main House was completed, the family moved from The Brick House to a new brick house at High Acres Farm.
During the 1950s, High Acres Farm continued to evolve, with the construction of the barn, stables, shed, and office, and the relocation of the “Trophy Room” building from the Brick House, for Harry to use as a lodge for entertaining friends.