Richard (Dick) Winne (1926 – 2025)

Richard F. (Dick) Winne was born June 2, 1926, and passed away peacefully surrounded by his son, daughter and granddaughter, and his sister and brother-in-law on June 21, 2025. He was born in Albany, NY and lived in Cherry Valley, NY where his father, Lewis F. Winne, and mother, Margaret R. Winne, raised him and his three siblings. In 1930 the family moved to Rhinebeck, NY. Dick grew up living in the Beekman Arms while his father ran the hotel as proprietor. The family then moved to Mulberry Street in Rhinebeck.

Dick met Elizabeth J. Wren. After marrying on June 3, 1967, the two remained in Rhinebeck and raised two children, Richard G. Winne and Tiffany B. Winne on Crosmour Rd. Prior to that he served in the Army Air Corp during World War 2 and attended Rensselaer Polytechnic Institute where he earned a bachelor’s degree in engineering. He went to work for his brother, Hawley, and eventually bought an Insurance Adjusting business from Hawley on June 1, 1982. He worked diligently in the same industry until January 1, 2007, when he sold the business to his son. He commanded respect and admiration by all of his professional peers. He and his wife, Betty, moved to Wilmington, NC to live out the remainder of their lives together with old friends and new friends they met.

Dick was a ribbon winning rodeo cowboy competing in trick riding and calf roping. He was a jokester, a Scout Master, an expert water skier, fisherman,  and he enjoyed many vacations with his wife, family and friends. Dick is an honorary member of the New York Association of Independent Insurance Adjusters. He served as the Village of Rhinebeck Tax Assessor from 1962-1985. He is a life member of the Hillside Fire Department. Dick joined the Dutchess County Fair Agricultural Society in 1963 and became a director in 1983. He served as past president from 1995 to 1996 and in 2011 was given an honorary membership. He worked  his way up from his first job at the fair, a cucumber judge, and ran the Dutchess County Fair horseshow for 52 years. He is a life member of American Legion Post 429 and a member of the Red Hook Society for the Apprehension and Detention of Horse Thieves, est. 1796. He “never wore sunglasses and never drank a cup of coffee a day in his life.” He survived a plane crash with his brother, Bob. Dick outlived most of his doctors.

Betty predeceased Dick on December 15, 2011. He is survived by his son, Richard G. Winne of Rhinebeck, NY and partner, Devon N. McGunigle, his daughter, Tiffany B. Winne of Phoenix, Az., and her two children Sophie and Zachary Priniski. He has many nieces and nephews who, along with their respective families, also survive him.

There will be a memorial service on Saturday, August 2, 2025, at the Dapson Chestney Funeral Home in Rhinebeck, NY from 11:00 AM to 1:00 PM followed by a military burial at the Rhinebeck Cemetery and finally a gathering for remembrance at the Beekman Arms Hotel. In lieu of flowers, please consider a charitable donation to The American Cancer Society.

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