Frank J. Orlando 1948 – 2022 BAILEY ISLAND – Frank J. Orlando, 73, passed away in his home on Bailey Island, Harpswell, this Thursday, May 5, 2022. Frank was born Dec. 3, 1948 in Andover, Mass., to Frank Joseph Orlando and Virginia Perkins Orlando. He grew up on Dale Street in the Ballardvale section of town with his sister Cynthia. He attended Andover High School and was a National Honor Society member, gifted singer and athlete; he played the leading male role in Kiss Me Kate and threw a no-hitter for the baseball team. In the summers he worked for his grandfather’s surveying business, often hitchhiking rides to work as his family did not own a car. Frank attended Salem State College where he earned a bachelor’s degree in math and later a master’s degree in school administration. After graduation, his first job was as a math teacher at Pentucket Regional High School. During a 26-year span at Pentucket, he earned promotions from teacher to guidance counselor, to vice principal and then to principal. In 1996, Frank became the principal of Reading High School, finally retiring from his career in education in 2004. Frank was the devoted husband of Margaret “Peggy” Orlando (nee Massaro) for 51 years. High school sweethearts, the two would go on to raise their three children in Andover. During this time, Frank enjoyed playing Rec Park softball and coaching his children on local sports teams. He was heavily involved in Andover Little League and was instrumental in bringing summer baseball tournaments to town. From childhood Frank was an accomplished singer. He participated in church choirs as a boy and continued to solo at South Church in Andover for many years. He was a member of the Andover High School choir, traveling to Austria one summer to tour. By the time he was a young adult, he was proud to be asked to sing at friend’s and family’s weddings and funerals. Later he sang with both the Atkinson Congregational Church choir in New Hampshire and the Bowdoin College Community Choir in Maine. Singing brought tremendous joy to Frank throughout his life. After retiring, Frank and Margaret moved to Bailey Island in Harpswell, Maine and felt the immediate warm embrace of the close-knit community. Frank especially cherished singing with the choir of the Islands Community Church. In this new home, more than anything, Frank enjoyed spending time with his grandchildren and hosting family and friends. He loved to reminisce about the good old days and share stories of his grandchildren’s accomplishments, beaming with pride as he spoke. Frank is survived by his wife, Margaret; children Dana (Marybeth) Orlando, Matthew (Carrie) Orlando, of Brunswick, and Laura (Paul) Bellacqua; his sister Cynthia (George) Milne; seven grandchildren Elizabeth, Matthew, Gabriella, Sofia, Francesca, Megan and Mason; and nephew David (Alison) Milne and their children Sarah, Derek and Christopher. A private ceremony will be held for family and close friends. In lieu of flowers, please send donations to: Orr’s and Bailey Islands Fire Department P.O. Box 177 Orr’s Island, ME 04066 (obifd.org) or: Islands Community Church P.O. Box 281 Bailey Island, ME 04003

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