Ruth Livingston Mills held countless functions at Staatsburgh during her lifetime, but one of the grandest affairs to happen at Staatsburgh was the wedding between the Millses' daughter Gladys and Henry Carnegie Phipps on December 7, 1907. It was very important for young women to find a suitable match and Ruth Mills would have devoted considerable time to securing the best match possible for her daughters. The engagement between Gladys and Henry was rumored in October 1907 after they spent time together in Long Island and it was announced in the New York Times in November. Family and friends tried to persuade the couple to have the wedding in New York, but both preferred the quiet pastoral setting at her family's Staatsburgh estate.
