Ruth Ann Winkler

Ruth Ann (Kosby) Winkler, 98, of Cuttingsville, VT, died on September 9, 2026 at Rutland Regional Medical Center. She was born February 8, 1928 in Hempstead, L.I., NY to parents Lawrence George, Sr. and Gertrude Cecilia (Spuhler) Kosby. 

In June of 1945, she graduated from Hempstead High School, N.Y. and began a lifetime of stenography, beginning as a typist at Grumman Aircraft Engineering Corp. in Bethpage, L.I., NY. 

She met and married her sweetheart, Conrad Kenneth Winkler, in 1951 just before the U.S. Army Signal Corp ordered he be sent to Germany to serve during the Korean War. She flew to Germany where she spent 7 months in Heslach, near Stuttgart, to join her husband. When Conrad was discharged, they settled in Plainview, NY and raised their two children, Jennifer Jo and Brian Conrad. 

Her husband became a co-owner and partner in the newspaper printing business in Freeport and in Westbury, L.I., NY and Ruth, still typing, became a typesetter. When grown, children Jennifer and Brian joined the personnel.

 In 1984, they retired to their beautiful home which they designed in Cuttingsville, VT. Ruth took a part time job at the Post Office while Conrad prepared and planted a garden and an orchard. She joined the town’s library staff and both joined the Shrewsbury Historical Society and enjoyed their volunteer work. Ruth became secretary for the Society and served for 29 years. 

Ruth also pursued the art of calligraphy under the tutelage of Michael Sull, teacher of the Spencerian hand and enjoyed her spare time making greeting cards sporting flourished capitals for her family and friends. 

Ruth and Conrad were communicants at St. Mary’s Church in Mt. Holly, which unfortunately burned down on December 30, 2007. She loved with all her heart her family, friends, and all the creatures great and small who joined the family through the years, most recently the adoption of two kittens Precious and Elke. 

Survivors include children, Jennifer Jo (Winkler) Lauri and husband Joe of Plainview, NY and son, Brian Conrad Winkler, Ruth’s caregiver in recent years, who resides in Cuttingsville, VT; a grandson, Michael Conrad Lauri and wife Angie and baby, Eric Joseph, born on New Year’s Day, 2023 all of Plainview, NY making Ruth a delighted great-grandma; and a niece, Donna Miller

She was preceded in death by her loving grandparents and parents; her beloved husband, Conrad of 65 years in 2016; and two brothers: Lawrence G. Kosby, Jr. in 1992, and Richard A. Kosby in 2019; and cousins, nieces, nephews, and many lifelong friends. 

Ruth will join her husband in the Shrewsbury Center Cemetery at a private graveside service.

 Memorial contributions may be made to the Shrewsbury Historical Society, c/o treasurer, Shrewsbury, VT 05738, the Tails of Hope-Rutland County Humane Society, 765 Stevens Road, Pittsford, VT 05763; or by planting a flower in your garden.

 Arrangements are made by Tossing Funeral Home. As requested, there will be no viewing hours.