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Charles Gilbert, 86, Former Principal In Ossining

Charlie Gilbert
Charlie Gilbert Photo Credit: Contributed

Charles “Charlie” Frederick Gilbert, formerly of Ossining, died on July 10.

He died peacefully at the Villages Hospice House near his home in Florida, following a brief illness. He was 86 years old. Gilbert was born to George H. Gilbert and Emily Lawrence Rohlfs Gilbert and raised with his two sisters, Emily and Janet in Ossining.

He attended Ossining High School and served as freshman class president. After graduating, he attended New York State Teachers College in New Paltz and later obtained a Masters from New York University. He played center on his basketball team in college. He also played the drums to help pay his way through school. He met his wife and soul mate Dorothy “Dottie” Ruth Gilbert in college. They were married for 52 years.

After a short time teaching in Ossining, he became a principal at Brookside Elementary School in Ossining. He was the youngest principal ever hired in Ossining at the time.

He created the popular Brookside Fair and is fondly remembered by his students and colleagues. He later served at Roosevelt School in Ossining, where he started an outdoor education program for inner city youth. He treasured his Brookside and Roosevelt colleagues, friends and above all his students. He touched the lives of many and was equally touched by their friendship throughout the years.

He was a loving husband, father and grandfather. Surviving is his second wife, Beverly Gene Gilbert, his three children, David Gilbert (Diane) of Cumming, Georgia, Jeffrey Gilbert (Kathleen) of Atlanta, Nancy Woods (Wayne) of Zebulon, Georgia, and his stepson, Andrew Parsons, his seven grandchildren, Kyle Gilbert, Curtis Woods, Keith Gilbert, Jessica Woods, Kelly Gilbert, Kevin Gilbert and John Henry Woods, and his nieces, Kerry O'Connell of University Place, Washington and Jill Torbett (David) of Marietta, Ohio.

The family requests that those wishing to honor his memory do so by contributing in his name to the Hospice Foundation of Lake & Sumter, Inc., 12300 Lane Park Road, Tavares, Florida, 32778 (

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