Allan William Strout

NAPLES/Windham – Allan Strout, loved and faithful husband, father, friend and all-around great guy passed away on Tuesday, Oct. 29, 2019 following several weeks of ill health. He was born in Gray on Sept. 13, 1946 and grew up in the Popeville neighborhood of Windham. There he fished and swam in the Pleasant River, made mischief with friends, worked on local farms haying and picking apples and snow-skied over self-made jumps behind the family home. He made friends easily because he knew how to be a friend. Relationships he formed through high school lasted throughout his life. He graduated from Windham High School in 1964.

Allan served with honor and distinction in the United States Army from 1964 to 1966, serving in Germany, Korea and Vietnam. While in Vietnam, he served as crew chief with the First Aviation Battalion where he earned his Soldiers Medal for heroism and various Air Medals.

Allan married Cynthia Caiazzo of Westbrook on Nov. 14, 1970 and, shortly after, moved to Bishop, Calif. where they raised their two daughters, Alicia and Cari. Allan had a great love of the mountains of the Inyo National Forest where he worked for the U.S. Forest Service for 33 years. After retiring, Allan and Cindy returned to Maine and built their retirement home on Trickey Pond in Naples. During his retirement, Allan enjoyed kayaking around the lake and was able to pursue his interest of a lifetime; designing, building and flying model planes. It was with great joy that he was able to make his planes fly over Trickey Pond, summer and winter. He was a member of the Propsnappers RC Club in Scarborough.

Allan and Cindy spent winters in New Mexico and Texas with their daughters, Alicia and Cari. Two granddaughters were the object of his loving attention in more recent times.

Allan is predeceased by his parents, Mildred and Ray Alley, his father, Arnold Strout; and his younger brother, Lawrence Alley.

He is survived by his wife, Cindy; daughter, Alicia Strout Molina and her husband, Hector of Alamogordo, N.M., daughter, Cari Strout Bennett and her husband, Colin of San Antonio, Texas; granddaughters, Kaylie and Kadence Molina; and sister, Melanie Alley of Windham.

A celebration of life will be held in the summer of 2020. Arrangements are in the care of the Windham Chapel of Dolby Blais & Segee, 434 River Rd., Windham, Maine. To express condolences or participate in Allan’s online tribute, please visit

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