The family history of Roger Hayward in the Northeastern United States stretches back to at least the eighteenth century when Peter B. Hayward, one of the area's first pioneers, settled in Surry, New Hampshire. Three subsequent generations of Haywards were thus born in Surry before Roger’s grandfather George Hayward made the move to Keene, New Hampshire in the mid-1800s.
Roger’s mother Ina was the daughter of William Preston Phelps, a celebrated artist who specialized in landscape with cattle as incidental adjuncts. Getting his start as a sign painter, Phelps eventually held a local exhibition that launched him into relative renown. In light of his skill, several area businessmen put together a fund so that Phelps could study and train in Europe. After a few years spent mostly in Munich (where he later became a founder of the Munich Art Club), and several more in Paris during a return trip, Phelps attained a considerable level of success as a minor painter in Lowell, Massachusetts before reacquiring his family’s farm near Chesham, New Hampshire. Phelps became enamored with the local Mount Monadnock, which he painted extensively, and for a number of years had a yearly show in Boston. He was also one of the first painters to set up a canvas on the brink of the Grand Canyon, and always thought he had beaten Thomas Moran to the draw of using that particular method.
During the years that Phelps spent in Europe, his family was brought along with him, and Roger’s mother Ina spent a full year in the Berlin public school system when she was 8 years old. Following the family’s final return to the United States, Ina spent most of her adolescent life in Lowell, Massachusetts. Like her father, Ina was an artist and later became responsible for managing her father’s works and estate. According to later reflections by Roger Hayward, his mother was brought up in a studio environment and had direct interest in painting and other small crafts. She believed “that one painted and drew just as one talked and wrote or did any other normal human activity,” a style of living that she later promoted in her children.
Roger Hayward’s father, Robert Hayward, married Ina Phelps in 1893 in Chesham, ten miles east of Keene. The couple returned to Keene late in the century and made their home at 101 Court Street. Robert Hayward had “a mechanical aptitude which he expected to exploit in watch and clock repairing.” However, early in his career he shifted towards work in manufacturing management, where he oversaw various cooperages. He was a general manager and superintendent of a firm that manufactured ‘cans’ - “pail like wooden containers for paint, pickles, fish and printer’s ink.” Later on he became manager and superintendent of a firm that manufactured the same items on a larger scale, but also “acted as general sales manager with half-yearly trips to cities on the eastern seaboard as far south as North Carolina.” Incidentally, the jeweler’s lathe that Robert had initially used for his mechanical inclinations was kept as a hobby and for family use, much to the future benefit of his son Roger.