Simon and Elizabeth Humphrey built the Trailing Yew around 1850. In 1892, their son William S. Humphrey and his wife, Violetta (Trefethren) purchased the house. Josephine Davis Day bought the house from the Humphrey heirs (daughters Nellie, Alice, Myrtie and Marion) and began renting rooms in 1926.
Business grew, and in 1928, Josephine hired William Stanley to build an “Annex”. The “Sea Gull” cottage was owned by Calvin Davis and in 1941, his daughters, Josephine and Virginia Davis, inherited the house. This was added to the Trailing Yew complex and after “Virgie’s” death in 1964, Josephine Day became full owner.
The Trailing Yew presently consists of eleven assorted buildings that provide housing for guests, cooking, baking and dining facilities, and staff housing.
On May 11, 1996, at the age of 99 years (just 37 days shy of her 100th birthday), Josephine Davis Day died. Josephine participated in cooking and serving meals for nearly 100 guests a day until the summer of 1994.
Josephine managed the Trailing Yew for nearly 70 years. The atmosphere at the Trailing Yew was, and remains, a family atmosphere. Josephine’s style is best represented in her own words. “When you run a place, you’ve got to treat your help like friends. They are my friends.” (May, 1995, New Monhegan Press) The Trailing Yew continues to be managed in the fashion that Josephine Day preferred.