LeRoy Gilbert Obituary

LeRoy Merle Gilbert, lovingly known as "Cowboy", by his friends passed away peacefully on January 1, 2025, at the age of 88 at the Jefferson County Health Care Center in Fairfield.
He was born on November 3, 1936, in the small town of Kilbourne, Iowa, the son of Gordon Towne and Evelyn Rosetta Ramsey Gilbert, Roy grew up on Monkey Mountain, where his childhood was filled with the simple pleasures of rural life. He attended elementary school in Kilbourne and later attended high school in Keosauqua. After completing his education, Roy ventured to Georgia, where he honed his skills in training racehorses. However, the pull of his roots proved strong, and he returned to Stockport, where he would lay down the foundation for his future.
On June 26, 1959, Roy married the love of his life, Dorothy Watson, in a quaint ceremony at the Little Brown Church. Together, they embarked on a journey to see them through various ventures and achievements. Roy's industrious nature led him to work in road construction, at the Ford Garage in Keosauqua, and at Prairie Grain. In 1962, he established a hog-buying station, later acquiring a grain elevator. His entrepreneurial spirit didn't stop there; Roy's passion for trucks materialized into a successful trucking company, transporting livestock, grain, rock, and more.
The 1970s marked a significant milestone for Roy and Dorothy as they purchased their first farm, further expanding Roy's business endeavors into agriculture. His brief foray into cattle farming inspired their son to start his own herd, continuing the family's connection with the land.
Roy was known for his active involvement in the Stockport Saddle Club, where his love for horses shone through. He made memorable rides to Fort Madison on horseback to the rodeos and even rode the Pony Express through Camp Courageous. Fishing and showing horses with his family were activities that brought immense joy to Roy, allowing him to share his passions throughout Southeast Iowa. In later years, he would share stories and adventures with the local coffee club at Pump and Pizza.
Roy's memory will be cherished by his wife, Dorothy, his son, Stuart Gilbert (Kaye) of Stockport, his daughter Cindy Hewitt (Mike Holcomb) of Agency, his grandsons, Wyatt Gilbert and Sam Dickinson (Kate), and his three great-grandchildren Serenity, Jaxson, and Olivia. He also leaves behind a host of extended family members and friends. Roy was preceded in death by his parents, his brother James Gilbert, and his granddaughter, Darby Gilbert.
A memorial service to honor Roy's well-lived life will be held on Tuesday, January 7, 2025, at the Cranston Family Funeral Home in Keosauqua at 11:00 AM, with a visitation one hour prior to the service. Following the service, Roy's cremains will be laid to rest at Spencer Cemetery, where he will be surrounded by the rolling hills and open skies he so dearly loved. Gifts in Roy's honor to a memorial to be designated later by the family may be left at the funeral home or mailed to the family at 26916 Route J16, Stockport, IA 52651. Friends may leave condolences online at www.cranstonfamilyfuneralhome.com.
Roy's story is one of a life well-lived, full of the things that mattered most to him: family, community, and the simple pleasures of country living. He will be remembered as a pillar of his community, a loving husband, father, grandfather, and friend.