Charles “Charlie” Stapleford, Jr.
January 9, 1939 - June 2, 2026
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.
Tina Sturgis
Charlie will be remembered fondly as part of all my Enduro memories over the last 15 years with my son’s, Bernie and Shawn St.Amand. Always a smile and genuinely happy to see you at an event. Such determination to still be racing in his 80s! We all will miss him. Peace and love to all his family who will miss him more.
Tina Sturgis
Chris nolan
He will be missed by me and anyone else that ever met him , my buddy thanks !
Sue Harrus
Dawn, Sharon, Celli, Church, Mr sincere condolences to all of you! Enduro’s were so fun & memories of you so young. Hope to see u Saturday. Sue Harris
Barbara welch
I’m lost for words
I’m so hurt for all of you…
You all know how I felt about him
Thank you for sharing him with me for 10 years
Sadly Barbara
Rick Meeker
Charlie was an institution in the world of Enduro racing, the ECEA and the Delaware Enduro Riders Club. I had the pleasure of serving as DER president for multiple years in the 80’s with Charlie guiding and directing me along the way. He will be greatly missed. RIP.
Rick Meeker
Ed Key
I was introduced to Charlie at a Delaware Enduro check point by Jerry Lloyd. Charlie was a stand up guy and will be missed by many .
David L. Scarpa
Charles was an inspiration to all that knew him. His enthusiasm was infectious and He never let anything hold Him back. Very sad news and my condolences to all of His Family and many Friends.
South Penn Enduro Riders
He was a great person, always there to help.
Barbara welch
Words escape me… I’m so sad
I feel your pain
He was a wonderful person proud of his family… thank you for sharing him with me for 10 years
He will be missed
Paul and Lois Loder
With Deepest Sympathy to Charlie’s Family and Friends. Charlie was a Great Guy !! Peace Always and God Bless…….
Philip Cruchley
Condolences to Charlie family
Lois Twigg
RIP Sir Charles. You will be missed. That smile and that laugh! Condolences to your family.
Helen McClure
We had a good ride and I loved every minute of it. You are my hero and I’ll miss you forever. My heart goes out to your family, friends, and enduro family. The mold was broken after you.
I love you,
Your Helen
Fred LaVance
About 20 years ago after finishing a D/S ride at Meteor Charley came & said “That was fun ” Turned around & rode the course in reverse R I P
Waverley and David Emmons
We are so shocked and saddened over Charlie’s passing. Our deepest condolences to all of his family and friends. The family vacations in Dewey were always a blast with Charlie; a ball of fun who brought so much love and laughter to us and our boys. We have many wonderful memories of our times on the porch at the cottage and 4th of July celebrations. He will be greatly missed. Charlie, we were blessed to have you in our lives. May you rest in peace. Waverley and David Emmons
Gregory King
I didn’t know Charlie very well, but I will always remember the contagious laugh and smile I saw on the trail.
I wish peace and prosperity to his family and friends. As well as his moto family.
He will be missed.
I hope to enjoy some funny stories one day told by his fans and friends. I’m sure there is more than a few.
I appreciate all he did for the Enduro community.
Bob Burton
Sorry to here about Charlie he was a legend among enduro riders Delaware Enduro Rider .
Donna Gill
Charlie was a rider I remember from my youth, when my Dad, Allen Triplett packed us up on the weekends to ride endure. At 77, his passing brings tears to my eyes. He is a legend.
Donna Triplett Gill
Rich and Dottie Farmer
We were deeply saddened to learn of the passing of Charlie Stapleford. What a great man and “force of nature” he was!!! He was an ardent supporter of Middletown sports where he excelled, but he became a huge supporter of the William Penn HS sports programs. Beginning in 1989, we began purchasing all of our vehicles at this small, but mighty dealership run by Charlie and his brother, Richard. We have been lifelong friends ever since. We knew we could have our cars serviced there with great care shown by the entire dealership. After moving to Georgia, each and every of our trips back to DE saw us stopping by to visit with Charlie, his son Chuck, and Richard. We cherish the memory of our last visit in July of 2025 as we sat down with them all to chat and catch up. We left that morning with spirits raised and smiles on our faces with the stories and past experiences shared. We loved Charlie and remain steadfast fans of this family. Our hearts go out to the entire family and wish we could be there for you all. You all will always be our friends, and we will be there for you in prayer and in spirit.
Bill Shamrock
I haven’t seen Charlie in years but the memories from those enduro days 30 years ago never fade because of Charlie. He was an inspiration and good friend to everyone he met, always cheerful no matter how tough it got. I think he has definitely shown what it means to “Don’t let the old man in”. Godspeed Charlie.
Stevie Hodgson
What a privilege to know and race with Charlie for so many years such a great man he will be truly missed but never forgotten
Bill Glenn
Charlie was a huge pillar in the Enduro world for so many many years and he took so many of us under his wing and lead, trained, guided, mentored us to become better riders with his knowledge of the sport. Nothing meant more to him than the success of the Delaware Enduro Riders and the joy of his family. It has been a privilege to have been one of his many students and reap the benefits of his expertise. See you at the gas stop one day. RIP Charlie.
Lisa, Lana, Colleen from Durty Dabber Motorcycle Club
Charlie was one of our all time favorite riders at our annual dual sport event in PA. He rode our event for many years and we stayed In touch with him throughout the year as well. He always had a smile, had the best time riding and socializing with all the riders who quickly became friends to him. Our event is a 2 day 100 mile ride and no one enjoyed it more than Charlie did. There were hero sections built into the course for those who felt up to a little more challenge for the day and Charlie always did the harder route with a smile and laugh and at times would turn around and do it again with that big grin we loved so much. He was signed up to ride our event the weekend of May 30/31 and we were very sad when we heard he would not make it. RIP dear friend, we love you and will miss you deeply. 💙
Kathi Cambell
I read this somewhere, written anonymously, and it certainly applies to Charlie.
“Life is not a journey to the grave with the intention of arriving in a pretty and well
preserved body, but rather to skid in broadside, thoroughly used up, totally worn out, and loudly proclaiming “WOW, What a Ride!!””
He was one of the most helpful individuals, and always offered reassuring support to me. He will be sadly missed.
Jackie cheezum
So sorry to hear the sad news. Charles was a dear friend to Glenn and I in Florida. We met him there a few years ago and enjoyed his company. We spent many evenings together dancing and having lots of fun. We will miss him. Please except our deepest condolences.
Peter Parlett
Charlie had a super power. Well, perhaps more than one. But the one I want to highlight is the superpower that Don Billing and I watched in action and experienced more than most. This was his uncanny ability to make people want to put out an inconvenient amount of effort and energy in an effort to feel they belonged to an enterprise much bigger than themselves and that their effort would be appreciated by Charlie. This would manifest itself when the AMA would request that the DER put on yet another national championship event, because the quality of our Enduros during the prime years was so outstanding. This was textbook leadership on Charlie’s part and this leadership molded many young members toward responsible adulthood and this legacy of maturity is Charlie’s greatest gift to the many generations of young riders he influenced to become adults.
I am grateful to have been his friend for 55+ years. I will miss his calls which often started with: “I have an idea and I think you might be the best to carry it out…” There is that leadership again. Have an idea and delegate. Thanks, Charlie.
Bob Conley Sr.
Thinking of Charlie, my Brother Ed went to school with Charlie. His smile and voice were electrifying. The Conley Family , Ed,Bob , Eileen, Karen,Steve of St. Georges Hieghts.
James Shea
Always a blast with charlie he will be missed.
Bob Hoover
” Forever ” —– Charlie—-
Dale Bendler
My sincere prayers and condolences to the Stapleford family on loss of Charlie 🙏
Tim Stancill
What a pleasure to have known you and riding with you.
Gods Speed.
Go fast TAKE CHANCES.
TIM.
John Palumbo
Everyone loved and respected Charlie
Chris "Vern" Kendig
Charlie was a true Ambassador to the sport of off road motorcycling and a genuinely great guy. My first experience at a big event I was fortunate to ride with Charlie and his group of friends. What fantastic memories of Charlie. RIP Charlie, thanks for your friendship very much.
Tammy Thompson
I am so sorry to hear of Charlie’s passing. I got my last 3 or 4 cars from him. I would see him when I we t for service and he was always friendly to me. Condolences ces to his children and to Richard.
Margaret MICHINI
My deepest condolences to Richard and the surviving members of the Stapleford family. Charlie was a friend of our family for three generations. May he rest in peace with Frannie and loved ones who went before. His sense of humour and community will be missed
Linda and Clarence Adams
For Sherry, Dawnie, Chellie, and Chuckie, yep, I said it because I still have great memories of you 4 little blond haired kids at the beach. Where it was a pleasure to try to help Fran try to keep up with you all. I was sorry to hear about Charlie. I thought he would live to be at least a hundred. He has moved on but Charlie is probably on a motorcycle working on being a legend somewhere else.
David Wiant
One heck of a guy and a true friend .My condolences to the the girls and Chuck and Richard.
Gabe Frezzo
Charlie was a force of nature. All who came in contact with him are better for that contact. Have had the honor to ride with the DER group for many years and have countless memories of those times. RIP Charles
Frederick Stapleford
Well Cuz, we shared some great times leaving me lasting memories. Whether in the woods, the field, the blind or the hunting lodge:-) Stories were told and shared. I’ll always remember that at just the right time you would tell one of your jokes. The best part was the ending with the famous Stapleford smile!
Rest in Peace.
Fred
Howard Moudy
Charlie deeply touched the lives of myself and my family (Regina & Bill). I met Charlie through Pete Parlett, and as a member of the Delaware Enduro Riders. There are so many great stories of races and clubhouse camaraderie. Some of my fondest and most heartfelt memories i have are of Christmas Eve at the Stapleford home with Charlie, Fran, their children, family and friends.
Charlie had a way of bringing out the best in people. I don’t think he ever met a stranger. He was rarely angry, smiled often, laughed, and caused others to laugh too. His memory lives on in the minds and hearts of his family and friends. He leaves a legacy of truly legendary proportion.
I already miss Charlie deeply. My most sincere condolences and prayers go out to the family.
Jamie Gamuciello
My sympathies to a wonderful family
Donna Cavender
I am so sorry I was unable to attend the service for your dad. I remember that he always had a ready smile and we would have a pleasant conversation whenever we would meet. I know this is a tough time and my prayers are with you.
Donna Cavender
Donna Austin White
On behalf of my family, please accept heartfelt condolences. My parents Harold & Eva Austin were great friends with Charles & Alice & Charles & Richard. Charles Jr was larger than life his entire life.
Richard, I know this is a difficult lose for you as was my sister. My thoughts will be with you & the entire family in the days, months & years to come .
Lenny Wehrle
Charlie, you were my main inspiration to keep on riding at 81.
You were, and still are.
Godspeed my friend.
Anna Legates
Charlie was a fun and vivacious Dewey Beach neighbor. Loved hearing about his motorcycle adventures. Especially when he & Fran traveled thousands of miles together.
Prior to my Key West trip, Charlie suggested an amazing travel itinerary.
And what a sense of humor. He will be missed.
Many spirits are dancing and celebrating with Charlie on board.
God Bless!
Anna Legates