Phillips Smith of Southport, Maine, passed away peacefully on April 23, 2023, at the age of 91 surrounded by family.

Born in Swampscott, Massachusetts in 1931, Phil attended Swampscott Public Schools, Hebron Academy, Williams College and Wesleyan University. His career started in the Navy in 1953, retiring as a LTJG. Following the Navy, Phil began his career and true calling as an educator and coach, teaching English and math at Westminster School in Simsbury, Connecticut. In 1966, Phil and Holly moved to Milwaukee, Wisconsin, where he continued to teach and served as the Head of the Upper School at University School. Phil was appointed the Headmaster of Trinity Pawling School in Pawling, New York in 1970, proudly leading and transforming his beloved community for 20 years. Under Phil’s steady leadership, Trinity Pawling grew and thrived. During Phil’s stewardship, the school’s enrollment increased and the endowment grew from $25,000 to $4 million. Another of Phil’s legacies at TP was beginning a youth hockey program from first grade through high school students. Always a sage mentor, Phil touched countless lives of students, their families, teachers, and staff, fervently believing that effort and drive must be acknowledged and rewarded. As such, Phil began the Language Retraining Program that supports students with learning differences. He and his family embraced every aspect of the school, cheering on athletic teams, beginning the day with an inspired reading at chapel, and guiding students and faculty to reach their full potential. As headmaster and throughout his retirement Phil served on several professional boards including as a trustee, chairman, and treasurer of New York Association of Independent Schools, trustee of Albany Academy for Girls in Albany, New York, the Peale Center for Christian Living in Pawling New York, The Edward E. Ford Foundation in New York City, The Kents Hills School of Kents Hill, Maine, and Hebron Academy, Hebron, Maine. In 1990, Phil and Holly retired to Southport while he continued to serve as Headmaster Emeritus.

Phil cherished his Southport community where he made a profession of volunteering and giving back to others. He was an integral member of All Saints by-the-Sea, serving on the chapel committee for several years. Phil passionately supported the Boothbay Region YMCA, serving as a trustee, chairman and co-chair of the capital campaign. Additionally, Phil served as trustee and chairman for the Boothbay Region Student Aid Fund, trustee at the Bigelow Laboratory for Ocean Sciences and the Boothbay Region Educational Foundation. He sat on the Long-Range Planning Committee for the Episcopal Diocese of Maine, and the Vestry at St. Columba's Episcopal Church.

Phil loved life and lived a life of giving. Always an educator, he dedicated his leadership and wise counsel to the YMCA, Trinity Pawling School, and the Church. He has touched so many lives. When he was not inspiring the next generation or helping raise money, he enjoyed spending time with family, reading three newspapers daily, sailing off the coast of Maine, playing bridge and immersing himself in a good novel. Phil was a friend to all whom he met, and he cherished his many life-long friendships.

Phil is survived by his beloved wife, Holly Fuller Smith, and loving father of Edward (Ted) Phillips Smith and his wife Penny Walker Smith, and Mark W Smith and wife Carrie Smith, and his grandchildren Evelyn Ramona Smith and her husband Eric Sprague, Harrison Spinney Smith and his wife Courtney Smith, Henry Phillips Smith, Penny’s children Maddie and Flynn Biddulph, and Carrie’s sons Walker and Jackson Danforth.

Family and friends are invited to a celebration of Phil’s life at 2 p.m. at St. Columba's Church on Saturday, May 20, followed by a reception at the Boothbay YMCA.

In lieu of flowers, donations may be made to Trinity Pawling School https://www.trinitypawling.org/giving, Boothbay YMCA https://boothbayregionymca.org/annual-giving.html , or Boothbay Region Student Aid Fund in memory of Phil Smith, PO Box 293, Boothbay Harbor, ME 04538.

Hall’s of Boothbay has care of the arrangements. To extend online condolences, light a candle or share a story or picture, please visit Phillips’s Book of Memories at www.hallfuneralhomes.com