Charles “Charlie” Stapleford, Jr.

Charles “Charlie” Stapleford, Jr., age 87, of St. Georges, DE, passed away on Tuesday, June 2, 2026.

Born in Wilmington, DE on January 9, 1939, he was a son of the late Charles E. and Alice D. (Maree) Stapleford, Sr. and grew up in St. Georges, DE.  He graduated from Middletown High School, where he was a standout athlete—football, baseball, track and field, and basketball—went on to Goldey Beacom Business School, and served his country in the Air National Guard for 10 years.  Charlie married his high school sweetheart, Frances Emerson, and they remained together until her passing in 2011.

He carried forward a proud family legacy as third-generation President of Stapleford’s Chevrolet and Oldsmobile in St. Georges, where he worked side by side with his brother Richard, who serves as Vice President. In the dealership as in the rest of life, Richard was Charlie’s partner, steadfast companion, and lifelong best friend.

An avid waterfowl hunter, Charlie loved the outdoors and enjoyed competition in all forms. He also loved country music, dancing, NASCAR, and classic John Wayne movies. In his later years, his competitive spirit was channeled into the game of Hearts, where marathon sessions with his grandchildren frequently ended in shouts of triumph or outrage.

But perhaps most of all, Charlie’s life was defined by his passion for motorcycles. A founding member of the Delaware Enduro Riders Club, he earned multiple regional and national enduro championships, was inducted into the East Coast Enduro Association Hall of Fame, and served as a referee for the ECEA for more than forty years. His dedication, sportsmanship, and contributions to the riding community earned him the respect and admiration of fellow riders throughout the country.

Charlie passed his love for enduro racing onto his son Chuck, and treasured the time they spent together at races up and down the east coast. Beyond competition, Charlie found freedom and joy on the open road. He loved exploring mountain roads, scenic byways, and destinations across the country on his Harley-Davidson Ultra Classic. He was at his happiest with two wheels beneath him and a new horizon ahead.

Charlie honored a commitment to his late wife Frances to always keep their family close, happy, and loved. He relished watching his grandchildren compete in sports, following their accomplishments with pride and exhorting them to, “When in doubt, give it more throttle,” and “Be the hammer, not the nail.”

Charlie did indeed live life at full throttle and on his own terms. He was, by universal acknowledgment, a force of nature, defying age, injury, and expectations. His 20th century grit and determination were balanced by his infectious laugh, natural charisma, and kind heart. He embraced every day with enthusiasm, courage, humor, and an unwavering sense of fun. His irrepressible spirit, charm, and love of life remained with him until the very end.

In addition to his parents, Charlie was preceded in death by his wife, Frances Ann (Emerson) Stapleford. He is survived by his children, Sharon Forge (Michael), Dawn Emmons (James), Michelle Stapleford (Joseph Casarino), and Chuck Stapleford (Shawni); grandchildren, Lex and Brynn Forge, and Jessica and Connor Emmons; brother, Richard Stapleford; and many nieces and nephews.

A visitation for family and friends will be held from 9 am until 11 am on Saturday, June 13, 2026, at Spicer-Mullikin Funeral Home, 275 E. Main Street, Middletown, DE, where a funeral service will begin at 11 am. Interment will follow in St. Georges Cemetery, Kirkwood-St. Georges Rd., St. Georges, DE.

In lieu of flowers, donations may be made in Charlie’s name to St. Georges Historical Society, P.O. Box 267, St. Georges, DE 19733; or to St. Georges United Methodist Church, P.O. Box 145, St. Georges, DE 19733.