Friday, March 20, 2026

Richard “Dick” F. Winne, 99

WILMINGTON — Richard F. Winne was born to Lewis F. and Margaret Hawley Winne in Cherry Valley, New York. It was Wednesday, June 2, 1926, — 99 years ago. Dick grew up and was educated in Rhinebeck, NY, graduated from RPI in Troy, NY.

He was 1 year old when the jukebox was invented.

He served in the Army Air Corps during World War II. He joined during the last year of the war and never saw combat but was trained as a pilot to fly a medium bomber. He also served as a Scout Master in the Boy Scouts.

On June 3, 1967, Dick married Elizabeth Wren. She predeceased him on December 15, 2011.

Dick once crashed a plane that was being co-piloted by his brother, Bob. He survived the crash but had to be in the hospital “the whole afternoon…”. He was also an expert water skier, once fastening a rocking chair onto a plywood disc and successfully traversing the boat’s wake,

Dick was a ribbon-winning rodeo cowboy, competing as a trick rider and calf roper. He competed in 52 professional rodeos.

He never wore sunglasses a day in his life nor drank a single cup of coffee. He has outlived most of his doctors, seeking young ones nowadays.

Dick served on the Dutchess County Fair Agricultural Society in New York as an honorary member. He worked his way up in the organization from his original job, which was cucumber judge. His father was president before him, and his son currently serves on the agricultural society. Dick ran their horseshows for 52 years.

He also served as Rhinebeck, NY village tax assessor from 1962-1985.

I must mention that in addition to all the above, Dick was also CEO of his own insurance adjusting business, Van Kleeck-Winne Adjusters. He is an honorary member of the New York Association of Independent Adjusters.

Dick is also a lifetime member of the Hillside Fire Department, a life member and oldest living member of American Legion Post 429, and a member of the Red Hook Society for the Apprehension and Detention of Horse Thieves which was established in 1796.

Dick is survived by his son, Rick Winne, his daughter, Tiffany and her two children Sophie Priniski and Zachary Priniski.

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