Henry A. Shaffer, Jr.

It is with deep sadness that the family of Henry A. (Dick) Shaffer, Jr., 79, of Elkton, MD, announces his passing on Monday, September 7, 2026, after a long illness. Even though family and friends grieve in his loss, there is much joy in the legacy he left us.

A lifelong resident of Cecil County, he was born in Baltimore, MD on February 28, 1947, to the late Henry A. Shaffer, Sr. and Mary Pauline (Siple) Shaffer.

Henry attended Elkton High School where he excelled in the classroom and in both baseball and football. Henry was a graduate of Tusculum College in Greeneville, Tennessee, where he received a partial academic-athletic scholarship, was a member of honor societies and was a 4-year varsity letter winner in baseball. He received his Master’s Degree in Administration from Towson University.

Upon graduation he was employed by the Cecil County Public Schools as a teacher and baseball and football coach. Other positions held during his 51-year career with the school system included Athletic Director, Assistant Principal, Supervisor and Director of Human Resources, Associate Superintendent, Superintendent of Schools, and Consultant to the Superintendent/Board of Education.

Over the years, Mr. Shaffer represented Cecil County Public Schools on various local, state and regional committees and task forces, including: Maryland Negotiator’s Service (Past President), Maryland Negotiator’s Service Labor Relations Assistance Team (Founder and Past President), Chief Negotiator for Cecil County Public Schools, Association of School System Personnel Administrators (Past Chairperson), Eastern Shore Personnel Directors Association (Past Chairperson), Business and Education Partnership Advisory Council, Cecil County Homeland Security Committee, et al.

Community involvement included membership in the Elkton Presbyterian Church, where he served as an Elder, Deacon, and lay preacher over the years, Union Lodge #48 AF&AM, the William F. Singerly Fire Company, the Board of Directors for the United Way, the NAACP, the Board of Directors of Northern Chesapeake Hospice, Cecil County Board of Election Supervisors (Past President), Elkton Planning Commission, Cecil/Harford Waterman’s Association, and the Upper Chesapeake Bay Museum. He was a recipient of the Cecil County Chamber of Commerce Donald Thomey Lifelong Service Award. This recognition cited his years of employment with the public schools and dedication to children and the community.

A beloved son, brother, dedicated husband, father, father-in-law, grandfather, and cherished friend to all who knew him, his greatest joy in life was gathering with his family and celebrating accomplishments of friends and loved ones. He will be remembered for his resilience, strength of character, charming sense of humor, optimism, generosity and willingness to help others. He approached life with a calm humility and treated everyone with a sense of kindness and caring. Henry lived a life filled with enthusiasm, hard work, adventure, kindness, humor, service, and devotion to the people he loved. His legacy lives on through his daughter, granddaughter, and loved ones, who will carry forward his values, lessons, and love.

An avid sportsman, Henry enjoyed hunting on the family farm, training rabbit dogs, boating, fishing and crabbing.

Henry is survived by his loving wife, Kingsley Hopper Shaffer, to whom he was married for more than 56 years; his daughter, Kimberly Miller (John), and granddaughter, Paige. In addition to his parents, he was preceded in death by his sister, Janet Virginia Shaffer, and brother, Jerome Davis Shaffer.

Memorial service will be held 2:30 PM, Sunday, September 27, 2026, at Elkton Presbyterian Church, 209 E. Main St, Elkton, MD 21921, with visitation beginning at 12 noon. Interment will be private in Gilpin Manor Memorial Park, Elkton, MD.

In Henry’s memory, contributions maybe be made to the Elkton Presbyterian Church, at the above listed address.

The family would like to thank Amedisys, Singerly Fire Company and all the friends for their comfort and support.