Kay Chiles

Kay Chiles, age 89, of Jefferson City, passed away peacefully Thursday, December 4, 2025, at Heisinger Bluff's.
She was born on July 12, 1936, the daughter of Charles August and Frances Evelyn (Wells) Hindman. She was married on June 6,1959, in Blytheville, Arkansas to Robert Chiles.
Kay graduated from Blytheville High School in 1954 and went on to continue her education at Mississippi State College for Women. She later moved to Jefferson City, where she made her home and became a lifelong resident.
Kay owned and operated her own business, the National Kiddie Ride Association, an insurance agency serving coin-operated machines. Before retiring, she sold the business in 2006. She took great pride in the work she built and the relationships she formed along the way.
She was a faithful and devoted member of Faith Lutheran Church, always willing to lend a hand and support its many activities. Her steady presence and quiet generosity made her a cherished part of the church community.
Kay found joy in life's simple comforts. She loved having milk and sugar with just a bit of tea, spending long afternoons playing card games and Scrabble, and getting lost in a good book. A talented piano player, she filled her home with music and warmth. A vanilla Coke from Whaley's Drug Store never failed to brighten her day. She never let her boys win a game just to be kind-she made them earn every victory, teaching them the same lesson she carried into all of life: that effort, honesty, and heart matter. Above all, Kay was most proud of raising her sons and becoming the home where everyone gathered. She cared for friends, family, and her children's friends with the same open heart, becoming, in time, everyone's mom.
One of the highlights of Kay's later years was attending her 50th class reunion, where she joyfully reconnected with her dear friend Bill Michael and his family-a friendship she cherished deeply. She adored her grandchildren and great-grandchildren, never missing a chance to spoil them with the same love, humor, and generosity she shared with everyone around her. Above all, Kay loved her family fiercely. Reflecting on her life not long ago, she smiled and said, "I had a really fun time," a simple and beautiful reminder of the joy she found in every chapter of her journey.
Kay is survived by her children, Robert Chiles Jr. (Kary), of Theodosia, Mo, Bill Chiles (Stacy) of Fulton, Mo., and Dave Chiles (Leslie) of Jefferson City, Mo.; bonus children, Laurie Fleeman (Will West), and Opie Boyce (Ardie); grandchildren, Jared Chiles (Misti), Kelley Carver (Jay), Katlyn Chiles, Halle Chiles, Brendan Chiles, Logan Chiles, Reece Chiles, and Alex Chiles; and five great-grandchildren and one more on the way.
She is preceded in death by her parents, Charles and Frances Hindman; and one sister
Visitation for Kay will be held from 10:00 a.m. until 11:00 a.m., Friday, December 12, 2025, at Faith Lutheran Church.
Funeral services will be conducted at 11:00 a.m., Friday, December 12, 2025, at Faith Lutheran Church with the Reverend Rich Steensma officiating. Graveside services and interment will follow at the Mokane Cemetery, Mokane, Mo.
In lieu of flowers, memorial contributions are suggested to St. Jude Children's Research Hospital, 501 St. Jude’s Place, Memphis, TN 38105.
Funeral arrangements are under the care of Freeman Mortuary.