Our beloved Harold F. Winstead Sr. entered eternal rest on December 11, 2024. He was born July 13, 1938, to the late June Franklin Winstead and Sally Fuller Winstead of Roxboro, North Carolina. Harold was a beacon of strength and resilience, and his journey through life was marked by extraordinary dedication and steadfast commitment to his family, his nation, and his community.
Harold accepted Christ at an early age and joined the Quinn Chapel A.M.E. Church in Roxboro, North Carolina. He attended Person County Public Schools. In high school, Harold was a 4-year letterman in football and served as a statistician for the basketball team. He graduated from Person County High School in 1956. After graduation, his call to service led him to the United States Air Force. He completed basic training in San Antonio, Texas, and was stationed in Biloxi, Mississippi. He served four years in the U.S. Air Force and received an honorable discharge in 1960 as Airman First Class. After his honorable discharge, he served in the United States Air Force Reserves for 3 years.
In 1960, Harold moved to Durham, North Carolina, and worked at Bates Phillips 66 Service Station. While there, he met the love of his life, Frances, and they were married in 1961. They were married for 53 years, and from this union, four sons were born: Harold F. Winstead Jr., Huron F. Winstead, Hilton F. Winstead, and Harrison F. Winstead. In every facet of his life, Harold epitomized the virtues of hard work, perseverance, and loyalty. As a beloved father, he raised his children with a strong sense of integrity and a grounding in the values of kindness and generosity.
In 1965, Harold was employed by Duke Power as a bus operator in Durham for 2 years. He moved his family to Portsmouth, Virginia, in 1967, where he worked as an operator for Carolina Coach Trailways until 1985. He drove the eastern corridor from Norfolk, Virginia, to Philadelphia, Pennsylvania. After Trailways, Harold entered entrepreneurship as a contract courier. His services included local and regional document and small package delivery. He expanded services to medical transport for patient office visits and dialysis appointments. He continued these services until November 2021, when he concluded 36 years as a successful businessman.
Harold was affectionately known as “Paw Paw“ by his grandchildren and “Pop Pop” by his great-grandchildren. He enjoyed cooking for the family and was an amazing cook. He enjoyed being a father, being with family, and watching his sons play sports. During his sons’ formative years in sports, Harold served as a Little League Baseball Coach, Cavalier Manor Athletic Association member, and Manor High School Boosters Club member. Harold also enjoyed attending Person County High School reunions and connecting with life-long friends. Some may be surprised to know that he enjoyed watching Westerns and Reality TV shows all night long.
He was preceded in death by Sally Fuller Winstead (mother); June Franklin Winstead (father); Frances Elizabeth Winstead (wife); Frances Winstead Anderson (sister); Charles Earl Winstead (brother); Annie Winstead Eubanks (sister); Margorie Winstead Brooks (sister); Harold F. Winstead Jr. (son) and Harrison F. Winstead (son).
Left to cherish his precious memory are his sons, Huron F. Winstead (Janice) and Hilton F. Winstead (Benita); daughter-in-law, Kathy Winstead; five grandchildren and four great-grandchildren; two sisters-in-law, Edna McKinnon and Ida Hutchinson; two brothers-in-law: Sandy Lewis and James Hutchinson; and a host of nephews, nieces, cousins, and friends.
Harold was a pillar of the Portsmouth community, and his wisdom and good humor will be deeply missed.
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Roosevelt Brown II says
December 15, 2024 at 7:13 amPlease accept my condolences and prayers for the entire family.
Rosevelt “Roe Que” Brown II
Robert W. Howard, Jr. (Rub) says
December 15, 2024 at 8:26 amCondolences on your loss. You and your family are in our prayers.
Nathaniel Pierre Armstrong says
December 15, 2024 at 1:25 pmPrayers to the entire family during these trying times.
Shelby Harris says
December 16, 2024 at 11:25 amMy sincere condolences to you and your family.
Karen Hollomon says
December 18, 2024 at 12:32 pmHuron, praying for comfort and peace right now to you and your family. I am so sorry for your loss.
Carlyle A. Brewington says
December 18, 2024 at 1:15 pmI offer my most sincere and heartfelt condolences to the Winstead Family at this time.
Brian Dowe says
December 19, 2024 at 1:58 pmMy brother, expressing sincere condolences on your loss.
Jason Hill says
December 21, 2024 at 10:16 amR.I.P. Uncle Harold! My condolences to the Winstead family! Hilton, Huron continue to stay strong! 🙏🏽
Jacqueline McMillan says
December 20, 2024 at 9:45 pmHilton and family my sincere sympathy and condolences. Please know that you are in my prayers.
Beatrice Wilson Powell says
December 21, 2024 at 7:28 amTo Huron, Hilton and each of your families, I send my deepest condolences with sympathy and love.
I will always remember the wonderful smell of your father’s pipe tobacco and his good nature.
May you find comfort and peace in memories of his constant love and support and know that he was esteemed by many and regarded with true affection. Peace and Power to you in Christ Jesus. Always💕
Beatrice Wilson Powell says
December 21, 2024 at 7:31 amTo Huron, Hilton and each of your families, I send my deepest condolences with sympathy and love.
I will always remember the wonderful smell of your father’s pipe tobacco and his good nature.
May you find comfort in knowing he was esteemed by many and regarded with true affection. Peace and Power to you in Christ Jesus. Always💕
Harold & Mary Pinckney says
December 21, 2024 at 3:01 pmOur sincere condolences to Huron, Janice & family! You are in our thoughts & prayers!🙏🙏❤️❤️
Christi Martin says
December 23, 2024 at 10:20 amTo the Winstead Family,
There are no words to express how one feels when a strong patriarch of the family has gone home to glory. Those of left behind battle with sadness, memories, and sorrow. There is hope in knowing that we don’t grieve like those who have no hope. We find peace with the fact that your father, grandfather, uncle, cousin, and friend is at rest and was loved by each of you. I pray your continued peace in the coming days. When all goes silent and tears began to fall, let them come as tears of joy!
Blessings,
Christi Martin