Leslie Herbert Simmons

PORT CHARLOTTE, Fla. – Leslie Herbert Simmons was born in South Portland, Maine, Aug. 2, 1928, the son of Newell Trefethren Simmons and Edith (White) Simmons. He passed away at the age of 92 on Nov. 15, 2020, at his home, with his wife and family by his side.

He was a loving father and husband for all the 67 years of their married life together. He married his wife and best friend, Jacqueline (Tibbetts) Simmons on Sept. 11, 1953, in the Town of Topsham Maine. He graduated from Freeport High School in 1946 and worked jobs around town until he was drafted into the Army December 1950, serving two years at Camp Cook California, returning home December 1952.

He and his wife bought a home in Freeport and lived there for seven years, moving to Durham, in 1960, to live on a farm, enjoying the many wonderful things country living can bring such as a garden, horses and other miscellaneous animals children love. He enjoyed many old fashion Thanksgivings and Christmas’s there with his family. He was hired by Trailways of New England in 1962, although he was gone from home on many Holidays and other occasions, he loved driving and people, so always enjoyed his work. During these years his job caused him to move his family two different times, once to Salem, Mass., and once to Hampton N.H., both were great adventures.

In 1980, he moved back to Freeport to a home he built, on the water on Lower Flying Point road, near where he had spent most of his childhood. He enjoyed being around the ocean and loved to sail, spending many overnights on their sail boat with their children and grand children. He explored the many islands in Casco Bay and up and down the Maine coast. When he retired from Trailways in 1986 he went to work driving for Freeport School department until 1998, he retired to Florida in 1998 after spending a few winters there.

When he took a vacation he always wanted to go to a warm destination. He and his wife enjoyed sailing vacations on the sailing ships in the Caribbean visiting many of the Islands. Hawaii, Bermuda and Mexico were also on his list. Greece was the choice one year, one of the most exciting places of all.

He is survived by his wife, Jacqueline of Port Charlotte, Fla.; daughter, Diana McKenna and friend Viktor Volkorez of South Portland; grandson, Jared Freeman, wife Megan and great-grandson son, Wyatt, of Freeport; son, Garrett Simmons, wife Kimberly and grandson Gavin of Port Charlotte, Fla. Leslie was predeceased by his father, Newell, mother, Edith, two brothers and their wives, Clyde and Vivian, Leo and Mary, and a son, Lee A. Simmons.

A graveside service will be held next summer in Freeport, at the Grove Cemetery.

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