Wilson Vinyard Gillespie Sr., affectionately known as “Pop,” passed away suddenly from heart failure at his home on Thursday, October 23, 2025, just weeks after celebrating his 88th birthday.
Born on October 3, 1937, in Milford, DE, to the late Lee Gillespie and Hazel Voss, Gillespie was remembered as a tough, hardworking man whose quiet nature often gave way to a playful and joking personality once he felt comfortable. Though he preferred solitude and declined most invitations, friends and family knew he could never resist a good milkshake.
Throughout his life, Gillespie worked in several professions, including service in the National Guard, truck driving, maintenance work, and self-employment as a roofing contractor. Many locals still recall his business, “Pop’s Construction,” and the signature promotional flyswatters and envelope openers that bore his name.
Outside of work, he enjoyed tinkering on projects and solving puzzles to keep his mind sharp. A devoted member of the Milford Church of God, Gillespie also served for many years as a fire policeman with the Ellendale Volunteer Fire Company, where he was a lifetime member.
He was preceded in death by his wife, Anna Mae Gillespie (Walls); son, Howard Gillespie; daughter, Mary Wothers; a grandson; a great-granddaughter; five brothers; and one sister. He is survived by his sister, Kathryn Hall; brothers, Charlie and David Gillespie; and his children, Anna Marie Hamblin (Bob), Wilson Gillespie Jr. (Karen), and Sarah Jones (Norman). His legacy lives on through ten grandchildren, twenty-seven great-grandchildren, and seven great-great-grandchildren.
Funeral services were be held Thursday, October 30, 2025at the Ellendale Fire Company. Interment followed at Slaughter Neck Cemetery.
