Joseph Bobbie "Joe" Gupton, Sr.

Joseph Bobbie "Joe" Gupton, Sr., 85, fought the good fight then passed away peacefully on November 6, 2025, in Richmond, Virginia. Born on January 7, 1940, Joe lived a full and rich life marked by dedication to his family, his work, and to the so many people he met along the way. Most of his life was spent in southside Virginia, calling Petersburg home for over fifty years.

Joe grew up on a farm in Dinwiddie developing a love for country life and a strong work ethic. Little did he know that the work ethic he adopted on that farm would empower him for the rest of his life. A proud graduate of Sunnyside McKinney High School in 1957, Joe went on to serve three years in the U.S. Army as a personnel specialist. His service took him to Okinawa for two years, with additional time spent in Ft. Jackson, SC, Ft. Benning, GA and Ft. Rucker, AL. Joe nearly died from a bacterial pneumonia in 1960 and was honorably discharged from the service in 1961. This early life chapter instilled in Joe a strong sense of duty that would characterize his relationships and work for the rest of his life.

Joe spent over sixty years in the travel industry—a career that became both his livelihood and his passion. He began as a ticket agent and later served as a Traveling Passenger Agent (TPA) for Carolina Coach Buslines. Joe's journey continued as a bus station manager for both Trailways Buslines and Greyhound Buslines before becoming sales manager for James River Buslines in Richmond, VA. Through leadership, wisdom and service Joe helped grow each business he worked for, being proud of the financial growth that accompanied business success. Alongside these roles, Joe’s entrepreneurial spirit led him to create Gupton Travel Agency—a side venture that helped groups plan trips to fun and even exotic destinations. His deep knowledge of travel logistics and his genuine enthusiasm for helping others explore and enjoy the world made him a trusted figure in the industry.

Beyond his professional accomplishments, Joe had a simple yet profound trust in God through Jesus Christ—a faith that grew and developed throughout his life. He was a beloved husband to Martha Camden Gupton until her passing, and together they grew a family rooted in love and connection.

Joe is remembered with deep love and affection by his four living children Vicki Martin (Ricky), Bobby Ayres, Steven Gupton (Stephanie), and Michael Gupton (Kim), twenty grandchildren and twenty-two great-grandchildren. He was predeceased by his wife Martha and their son Joseph Bobbie "Joe-Joe" Gupton, Jr.

Those who knew Joe will remember him as a man who absolutely loved connecting with people. Whether it be meeting and chatting with strangers or having a beer and chatting with family, old friends and acquaintances, Joe thoroughly loved and enjoyed talking with people. He found joy in reminiscing and sharing about Petersburg from yesteryear and his experiences when working with all kinds of people in the travel industry through the years.

A lover of old school country music and an avid NASCAR fan, Joe brought energy and warmth wherever he went. His presence was steadying; his stories were rich with heart, humor and character; and his smile could lighten up and encourage even the heaviest of hearts.

May Joseph Bobbie "Joe" Gupton, Sr.’s memory bring comfort to all who knew him—and may the legacy of kindness he shared continue to inspire those whose lives he touched.

A Celebration of Life will be held at 11:00 a.m. on Saturday, November 15, 2025, at the Crater Road Chapel of the E. Alvin Small Funeral Homes, 3935 S Crater Road, Petersburg, VA 23805. The family will receive one hour prior to the service from 10:00 a.m. to 11:00 a.m. at the funeral home. Joe’s son, the Reverend Dr. Steven R. Gupton, will be officiating the service. Entombment will take place privately Southlawn Memorial Park.