Randall "Randy" V. Phelps Sr., a man known for his quick wit, adventurous spirit, and generous heart, passed away on June 26, 2026, in Windsor, Virginia. He was born on May 24, 1944, in Baltimore, Maryland, and lived a full and remarkable life of 82 years.

For 40 years, Randall proudly served his community as an Allstate insurance agent, helping countless families protect what mattered most. In addition to his insurance career, he dedicated 22 years as a Portsmouth Auxiliary Police Officer, earning the respect of his colleagues and the community through his professionalism, integrity, and sense of humor.

Randall embraced life with enthusiasm and never passed up an opportunity for adventure. As a licensed private pilot, he found great joy in flying and cherished every opportunity to take to the skies. He was also an avid motorcycle enthusiast who loved the freedom of the open road, especially when it led to the beauty and serenity of the mountains. Whether flying above them or riding through them, the mountains were one of his favorite places to be. When he wasn't flying or riding, he could often be found hunting, fishing, or enjoying the outdoors. Randall also had a special admiration for eagles, whose strength, freedom, and grace reflected the way he viewed life and the world around him.

He was a founding member of the Portsmouth Flyers Club and remained active throughout his life in numerous civic and professional organizations, including Portsmouth Community Concerts, the Windsor Ruritans as "Cookie Monster", the National Association of Insurance and Financial Advisors (NAIFA), Employer Support of the Guard and Reserve (ESGR), and the Knights Templar of the Monitor & Merrimac. His commitment to service and fellowship left a lasting impact on everyone who knew him.

Randall is lovingly survived by his children, Randall V. Phelps Jr.; Yvette Roberts (Willis); and Leigh-Ann Blount (Nick); his stepchildren, Renée C. Wright (Wade), Chris Hearn (Addison), and Corey Hearn (Cara); his grandchildren, 'Nikki' Khalaf (Mikey), Erin Ross, Kelley Roberts (Will), Cheyanne Oxendine, Cadance Blount, Ezra Blount, and Nova Blount; and his great-grandchildren, Mason Shea, Casey Khalaf, Addison Khalaf, and Ryan Khalaf.

He was preceded in death by his parents, Clarence F. Phelps and Mattie Bell (Chavies) Phelps.

Family and friends are invited to attend his funeral service on Wednesday, July 8, 2026 at 1:00 pm, at Parr Funeral Home & Crematory. Burial will follow at Greenlawn Memorial Gardens. More than anything, he would have wanted those gathered to share stories, laughter, and perhaps even a few well-worn puns in remembrance of the many lives he touched.

Randall will be remembered for his unwavering dedication to his community and his ability to make every ordinary moment feel like an adventure. Whether he was helping a neighbor, serving his community, piloting an airplane, riding his motorcycle through the mountains, casting a line into the water, or simply watching an eagle soar overhead, Randall lived life to the fullest and inspired others to do the same.

Fly high, Randall. May your spirit forever soar with the eagles you so admired. You will be deeply missed and forever remembered.