Harold William Castleberry Sr., age 87, of Glen St. Mary, Florida, passed away on Friday, May 27, 2022, at St. Vincent's Medical Center in Jacksonville. He was born on February 3, 1935, in Adel, Georgia, to Roy and Emma James Castleberry. Some of Harold's favorite things in life were driving his 18 wheeler, fishing with his grandchildren, hunting, and riding back roads with his wife. He was a loving and devoted husband, father, grandfather, great-grandfather, brother, uncle, and friend who loved to pick at you when he had the chance. Harold was preceded in death by his parents; brother, James Castleberry; and sister, Mary Castleberry. He leaves behind his loving wife of 66 years, Mary Lou Castleberry of Glen St. Mary; sons, Harold W. Castleberry Jr., Randy L. Castleberry (Marian), and Dale Castleberry (Christina), all of Macclenny; daughter, Debbie Combs (Marshall) of Perry; brothers, Howard Castleberry of Adel, Georgia and Marvin Castleberry of Callahan; sister, Gladys Stanfield of Moultrie, Georgia; 13 grandchildren; 16 great-grandchildren; 2 great-great-grandchildren; along with nieces, nephews, other family members, and friends. A Memorial Service will be conducted at 7:00 p.m. on Friday, June 3, 2022, at Blackburn-Curry Funeral Chapel with Pastor Marshall Combs officiating. Visitation with the family will be held one hour prior to the service at the funeral home. Cremation arrangements are entrusted to the care of BLACKBURN-CURRY FUNERAL & CREMATION, 380 N. Lowder Street, Macclenny, Florida 32063. (904) 259-2806. Please share your condolences with the family online at www.blackburncurryfh.com.