Harold Ray Caldwell, 75, of Kingston, Oklahoma, passed peacefully from this life in his home surrounded by his family on May 1, 2025. Harold was a loved father, grandpa, brother, uncle, cousin and friend. Harold was born December 4, 1949, in Altus, Oklahoma, to Paul and Edna Margaret Caldwell. He was preceded in death by his parents Paul and Margaret Caldwell; son Scotty Caldwell; daughter-inlaw Kacy Caldwell; brothers, Willie Earl and Arthur Lee Caldwell; and sisters, Linda Voyles, Leta Marie and Cheryl Ann; and many other family and friends. Harold is survived by daughters Cynthia Shields and Russ of Choctaw, Oklahoma; and Stephanie Harrison and Shane Thomas of Kingston, Oklahoma; brother Frank Caldwell of Kingston, Oklahoma; sisters Rita Harmon and Don of Marlow, Oklahoma; Peggy Sirmons and Wade of Justin, Texas; and Patsy Thompson of Kingston, Oklahoma; grandchildren Zachary Clark and Kenzi of Oklahoma City; Tatum Gauthier and Felicity of Choctaw, Oklahoma; Jaxson Gauthier and Hailee of Choctaw, Oklahoma; Josh Caldwell and Jennifer of Noble, Oklahoma; Brittney Miller of Arkansas; and Jessie Thomas and Hulsey Thomas of Kingston, Oklahoma.
Harold was also blessed with two great-grandchildren Nash Caldwell and Kendall Clark.
The Caldwell family settled in Maysville when Harold was a boy. Harold and his siblings grew up and made many memories there hunting, fishing and farming. Harold stayed in southern Oklahoma his whole life and did a variety of jobs. In 1993 Harold moved to Lake Texoma where he was a contractor, owning and operating his own construction company. There wasn’t a thing he couldn’t build or fix. As Harold began to age, he turned from construction to running a successful mowing and yard care business. He enjoyed getting to visit with his customers and many became like family. One of Harold’s greatest joys was teaching his grandkids the business he cared so much for and the value of hard, honest work.
Harold loved spending time outdoors, on the lake fishing, in a creek noodling or sitting in the deer woods waiting for the perfect shot. He would often joke that he was going fishing but would be back soon to go hunting. His sense of humor and laughter were contagious to those around him. When he wasn’t outside you could catch him playing a hand of poker or game of dominos with family and friends or watching a good western on TV. Harold loved his family and will forever be missed by those who knew and loved him.
Funeral services were Wednesday, May 7, 2025, at First Assembly of God Church in Maysville, Oklahoma. Burial at Maysville Cemetery in Maysville, Oklahoma, under the direction of John W. Williams of Winans Funeral Home. Words of comfort may be sent to the family at winansfuneralhome.com.
