Shirley Kay (Pilcher) Winter

July 27, 1940 - May 13, 2023


Shirley Kay (Pilcher) Winter, of San Luis Obispo, California, passed away peacefully with family by her side on Saturday, May 13, 2023, after a brief illness. Shirley was born on July 27, 1940 in Wheatland to Loyd Charles Pilcher and Elizabeth Claire Hardee. She attended Guernsey-Sunrise High School and went on to receive her Bachelor of Science in Education degree in 1962 from Chadron State College in Nebraska. It was at Chadron State that she met and married Gary Winter in 1961. Together they had five children; Kent, Todd, Scott, and the twins, Connie and Lisa. One of Shirley’s greatest achievements was receiving her Master’s Degree in 1973.


For her first six years, Shirley’s home was in Lusk and Torrington, until her family moved and settled in Guernsey, Wyoming. During her younger years, she and her family traveled all over the United States, eventually having visited all but one state. The only state missing was Hawaii, but for her 73rd birthday, she was surprised with a trip to Oahu to claim her fiftieth state. Some of her favorite places were close to home, including Yellowstone Park and the Black Hills of South Dakota.


Shirley enjoyed her membership in Job’s Daughters as a young woman and received the highest office of Honored Queen. Afterwards, she had long-standing membership in the Order of Eastern Star, where she was later installed into the top office of Worthy Matron of her local chapter. She was recognized with her 50-year pin in 2010.


Shirley taught elementary school in Guernsey, McCook, Nebraska, Wheatland, and Meeteetse. She moved to Laramie, for a few years until she moved back to Guernsey to be closer to her Dad. While back in Guernsey, she worked for the Goshen County School District’s Transportation department in Torrington until she retired. For the last 13 years of her life, Shirley and her beloved cat, Beau, lived in beautiful San Luis Obispo, California. There, she enjoyed the beaches and warm weather, wine tasting with her daughters, and travelling around the central coast.


Although Shirley pursued a career in education, she always had a love for music. While attending Chadron State, she was a member of the college band and the elite chorus ensemble, the Eaglaires. She enjoyed entertaining audiences with her angelic voice and participated in various local productions. She always wished she had pursued singing Opera professionally, but instead her neighbors and kids were gifted with that wish.


Shirley was preceded in death by her parents and her son, Todd Winter. She is survived by her sons, Kent (Georgia) Winter and Scott Winter; her daughters, Connie (Shannon) McNamara and Lisa Winter; her grandchildren, Brittany (Jeremy) Zint, Casey (Alyssa) Winter, Andrew (Ashley) Winter, Michaela Winter, Shailynn Winter, Aidan Winter, and Alanna McNamara; as well as numerous great grandchildren. Those who met Shirley always regarded her as kind lady with a smile always on her face. She will be greatly missed by all who knew and loved her.


Shirley was passionate about helping find homes for the many furry, four-legged creatures of her community. If you would like to consider a donation in her memory to the Woods Human Society of San Luis Obispo, please visit