Kenneth Wilson Bailey Sr., age 77, passed away unexpectedly after a brief illness on June 8, 2025, in Virginia Beach, Virginia. Born on April 5, 1948, in Norfolk, Virginia, Kenneth lived a life filled with love, integrity, adventure, and dedication. A man of loyalty, forgiveness, love and a passion for living, his passing leaves a great void in the lives of those who knew and loved him.
He was preceded in death by his parents, Joseph L. and Mary R. Bailey, and his brother, Phillip Lynn Bailey.
Kenneth is survived by his beloved wife of over 57 years, Diana Lee Bailey; his son, Kenneth Bailey Jr., and his wife Terry; his treasured grandchildren, Leslie Madison Bailey and Ryan William Bailey; his brother, Larry Leslie Bailey, and his fiancé Kathleen Matthews; his brother Phillip’s daughter Dyan; bonus “grandchildren” Destiny and her son Levi, and Summer and her fiancé Kianna; and his beloved canine companion, Sophie, who offered him unconditional love and companionship until the end. He also leaves behind countless aunts and uncles, nieces, nephews and cousins, who loved him dearly.
He began his Civil Service career in 1967 as an apprentice aircraft painter at the Naval Air Rework Facility. That apprenticeship included training as a draftsman and, based on that training, the engineering firm, McGaughy, Marshall, and McMillan, hired him. Some of his work there included projects for the U.S. Army Corps of Engineers who offered him a position that became his career for over 30 years. After study at Old Dominion University, he earned his Professional Engineer license in 1994, and rose from draftsman to Mechanical Engineer to ultimately becoming Deputy Division Chief, Technical Services Division, before he retired in 2006. His work was a testament to his commitment to excellence and innovation. He tirelessly contributed to projects that supported and protected our communities and our nation, leaving a lasting impact on all who had the privilege to work alongside him.
Outside of his professional life, Kenneth found great joy in the outdoors, nurturing a lifelong passion for camping, fishing, and exploring the beauty of nature, especially at their cabin in North Carolina. Soon after his retirement, he hiked a large portion of the Appalachian Trail. Taking trips with his family brought him immense happiness, and those cherished adventures became the foundation of countless treasured memories. He also loved road trips in his red Corvette. In his later years, Kenneth discovered an enthusiasm for reading, especially biographies, World War II and Civil War history, the Old West, historical novels, humor and mystery.
Kenneth possessed a dry sense of humor that could bring a smile to anyone’s face, and his wit and warmth were a constant source of joy for family and friends alike.
A Celebration of Life will be held at Altmeyer Funeral Home Southside Chapel on July 26, 2025, at 2 p.m., where loved ones and friends will gather to honor Kenneth’s life and legacy.
Kenneth was deeply loved and will be missed dearly by all who knew him. His life inspires us to embrace each day with gratitude and joy, following in his footsteps to seek out the beauty in every sunrise and the laughter in every moment.
To honor him, please consider donating to Coastal Virginia Conservancy, the Elizabeth River Project, or the environmental conservation organization of your choice.
