Frederick Gilbert Bourne was a self-made millionaire who resided at the Dakota Apartments in Manhattan and had a 1,000-acre estate in Oakdale, Long Island, called Indian Hall. Bourne became the fifth president of the Singer Sewing Machine Company, which is where the current name “Singer Castle” comes from. While the Bourne’s summered here, they called the castle, “The Towers” and the island, “Dark Island”.

Edith Wharton was part of “Olde New York” society, and is credited with establishing interior design as a profession in the United States. She was the first woman to receive the Pulitzer Prize for non-fiction for her book, Age of Innocence. She believed that good architectural expression included order, scale, and harmony.

George C. Boldt, a millionaire associated with the Waldorf Astoria and the Bellevue-Stratford Hotels in New York City, built this 120-room castle to display his love for his wife, Louise, on picturesque Hart Island, which he re-named Heart Island. Not a single detail or expense was spared in creating the grand castle with tunnels, Italian gardens, playhouse and powerhouse. Construction was ordered to start in 1900 on Heart Island in the Saint Lawrence River, and part of the Thousand Islands.