Harold Ray Caldwell, 75, of Kingston, Okla. passed peacefully from this life in his home surrounded by his family on May 1, 2025. Harold was born on December 4,1949 in Altus, Okla. to Paul and Edna Margaret Caldwell.
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 was a loved father, grandpa, brother, uncle, cousin and friend. He loved his family and will forever be missed by those who knew and loved.
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; 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, Okla.; Stephanie Harrison and Shane Thomas of Kingston, Okla.; brother, Frank Caldwell of Kingston, Okla.; sisters, Rita Harmon and Don of Marlow, Okla.; Peggy Sirmons and Wade of Justin, Texas and Patsy Thompson of Kingston, Okla.; grandchildren, Zachary Clark and Kenzi of Oklahoma City; Tatum Gauthier and
Felicity of Choctaw, Okla.; Jaxson Gauthier and Hailee of Choctaw, Okla.; Josh Caldwell and Jennifer of Noble, Okla.; Brittney Miller of Arkansas; Jessie Thomas and Hulsey Thomas of Kingston, Okla.; great grandchildren, Nash Caldwell and Kendall Clark.
Funeral Services will be held at 2:00 p.m., Wednesday, May 7, 2025, at First Assembly of God Church in Maysville, Okla. Burial will be at Maysville Cemetery under the direction of John W. Williams of Winans Funeral Home in Maysville, Okla. Words of comfort may be sent to the family at www.winansfuneralhome.com