Wilson Vinyard Gillespie, Sr.

Wilson Vinyard Gillespie Sr. (Pop), of Lincoln, DE, passed away suddenly from heart failure at home on Thursday, October 23, 2025, just weeks after his 88th birthday.

Wilson was born on October 3, 1937, in Milford, DE, to the late Lee Gillespie and Hazel Voss.

Wilson was known as a tough-as-nails man whose initial shyness quickly gave way to a joking, big-kid personality once you got to know him. He kept to himself a lot and turned down most invitations but would never pass up a milkshake. He was a dedicated worker throughout his life, holding many positions including service in the National Guard, a truck driver, a maintenance man, and a self-employed contractor specializing in roofing. Many still have the promotional items from his business, “Pop’s Construction”, such as his advertising flyswatters or envelope opener magnets.

In his spare time, Wilson enjoyed tinkering on various projects and keeping his mind sharp with puzzles. He was a faithful attendee of the Milford Church of God on Sundays and was a lifetime member and long-time fire policeman with the Ellendale Volunteer Fire Company.

Wilson was preceded in death by his beloved wife, Anna Mae Gillespie (Walls); his son, Howard Gillespie; his daughter, Mary Wothers; a grandson; a great-granddaughter; five brothers; and one sister.

He is survived by his sister, Kathryn Hall; his brothers, Charlie and David Gillespie; and three wonderful children he raised with Anna Mae: Anna Marie Hamblin (Bob), Wilson Gillespie, Jr. (Karen), and Sarah Jones (Norman). His legacy continues through ten grandchildren, twenty-seven great-grandchildren, and seven great-great-grandchildren.

Funeral services will be held on Thursday, October 30, 2025, at 11:00 AM with a visitation beginning at 10:00 AM at the Ellendale Fire Company, 302 Main St, Ellendale, DE 19941. Interment will follow immediately after services at the Slaughter Neck Cemetery. Arrangements are in the care of Berry-Short Funeral Home of Milford, DE.