William F. Phinney, 97, of New Harbor, ME died peacefully, at St. Andrew's Village in Boothbay Harbor, Maine, on February 28, 2026, with his son Nathaniel at his side. The third and youngest son of the late Reverend Arthur O. and Lucile F. Phinney, Bill attended Longwood Day School, St. Mark's School, and Harvard College and served as a United States Army intelligence officer in Washington, D.C., before marrying his life-long and beloved companion Perry F. Phinney in 1954, and embarking on a life-long career in educational leadership at the Dexter School in Brookline, Massachusetts.  

Following her lengthy illness toward the end of the lives they spent devoted to each other, Perry predeceased Bill on October 13, 2023, at their New Harbor, Maine home. The daughter of the late Robert H. Flynt of Monson Massachusetts and Cincinnati, Ohio and Wynn B. Flynt of Cincinnati, Ohio, she attended Hillsdale Preparatory School and Wellesley College, majoring in music, later serving as a longtime active alumna volunteer and as a class marshal at her 50th reunion.  An accomplished pianist, she loved playing on her Steinway throughout her life. After teaching several years at the Fessenden School in Newton, Massachusetts, she was "recruited" by Bill to join the Dexter faculty when he succeeded Reverend Francis Caswell as Headmaster in 1964. There, and later at Southfield, Dexter's sister school founded in 1992, she delighted in providing piano accompaniment for the voices of the students at assemblies, musicals, and concerts until their retirement in 2011.  Over the course of her long tenure, she took on many responsibilities including teaching second grade, serving as school librarian, organizing Prize Day, publishing the school’s Annual Report and managing mailing lists of donors and parents.  Perry’s excellent administrative skills and wise counsel were critical to the Phinneys’ success in running the schools.

At Dexter, Bill excelled from the outset in teaching boys, especially in Grades 4 and 7. Even today, many graduates, now in their senior years, fondly recall Bill as their best and favorite teacher.  As Headmaster, a role in which he served with great passion and purpose for 47 years, his impact on the life and evolution of the school was profound. Under his leadership in the late sixties, Dexter relocated from its small city block campus on Freeman Street in North Brookline to its current 36-acre site on Newton Street in South Brookline, a move that allowed for significant expansion of new academic, athletic, and artistic facilities and far broader educational opportunities for all the students.  Bill implemented a strong, traditional curriculum with focus on mathematics, reading, writing, grammar, and public speaking- the enduring foundations of the present-day Dexter Southfield education for both girls and boys. He also continued many of the tried and true traditions that remain central to the school, such as weekly assemblies, intramural and interscholastic competitions, and Dexter Southfield Day.  By leading the founding of Southfield School, he and Perry extended the same outstanding character and academic education to girls that the Dexter boys had long received. Hiring and mentoring a strong faculty was a critical aspect of the Phinneys’ leadership.  To quote a former faculty member, “Dexter indeed felt like a family directed by a paternalistic yet benevolent father figure. Each of us is proud to be members of that special family.”   

Having lived in Dedham for many years, the Phinneys made their home at Dexter after the new campus was established on Mt Wally.  They spent summers at the family cottage in New Harbor, which had been built by Bill's grandfather Frederick M. Flagg in 1906.  In the mid-1970’s, they purchased the Gosnold Arms Inn just a short walk down the street from their cottage, operating it in the summer and early fall seasons for many years, thanks to the managerial expertise of their daughter Lucy and her husband Kris.  When they retired, Bill and Perry moved full time to New Harbor where they enjoyed hosting many family reunions and overseeing their properties. 

They are survived by their sons, Robert and Nathaniel; their daughter, Lucy and son-in-law Kris Martin; three grandsons, Matthew, Tucker, and Nicholas Phinney; and many nieces and nephews. 

Their internment services were private. 

Arrangements are under the direction and care of the Strong-Hancock Funeral Home, 612 Main Street, Damariscotta, ME 04543.  Condolences, and messages for their family, may be expressed by visiting: www.StrongHancock.com.