Philip Cummings came from solid Vermont stock. His mother, Addie Sarah Webster Smith, was born in Cabot, Vermont, in 1870, the eldest of four daughters of Lorenzo Dow Smith, proprietor of the Cabot Inn, and his wife Abigail, a descendant of Daniel Webster.
Addie loved books and learning and was fiercely proud of her Vermont heritage. After high school, she spent two years at a teachers' college in Montpelier, Vermont, before being hired to teach English at the Hardwick public high school.
In December 1898, Addie married Philip's father, Harry Foster Cummings, a Hardwick man four years her junior and a former student in her class. Addie gave up teaching soon after she married to keep house for her husband and Philip, the couple's only child, while caring for a series of elderly relatives.
Harry Cummings was the fourth of five children born to Edwin Foster Cummings and his wife Laura. Edwin farmed in Hardwick for many years before leaving Vermont for more profitable employment as a machinist at the US Armory in Springfield, MA. Laura and four of their children moved with him, while Harry stayed behind in Hardwick.
After finishing high school in Hardwick, Harry worked first as a farmer, then as a traveling salesman for a machine oil company, before finally finding his niche as a real estate and insurance agent in Hardwick. As his business grew, he became a prominent citizen of the town and a respected voice in the local business community. Unfortunately, Harry's forays into land development in Vermont and Florida were ultimately unsuccessful, leaving his family with a significant financial burden just as the cumulative losses of the Great Depression began to effect the local economy.
Harry died in 1934 after a prolonged illness. Addie remained in Hardwick after his death and died there in 1946.
For more about Harry's ill-fated real estate ventures, see: Patricia A. Billingsley, "How Highland Lodge Got Its Name," The Hazen Road Dispatch 36 (Summer 2011), 18-25.