John Stockton Hobart, affectionately known as “Stocky,” passed away peacefully on October 5, 2026, at his home in Hampton, Virginia, surrounded by his loving family.

Born in Newport News, Virginia, on November 7, 1952, he was the son of the late John Henry Hobart and Anne Payne Williamson Hobart. He was preceded in death by his sister, Lynne Hobart Bjarnesen, and his granddaughter, Iyla. He is survived by his wife of 40 years, Rosemary (Rose); his three sons, Matthew (Julie), Phillip, and William (Asana); his three grandchildren, Alexander, Violet, and Naomi; his brother, Mark Hobart (Rosie); and nieces, nephews, and cousins.

Stocky had a genuine love of life and treasured time spent with family and friends. An avid sailor since his youth, he loved nothing more than heading out onto the open water and seeing where the wind might take him. He especially enjoyed racing Pura Vida with friends and fellow crew members, sharing both the excitement of competition and the camaraderie of sailing. He was a member of the Hampton Yacht Club, where he served as Treasurer for several years. He delighted in sharing his love of sailing with his sons, creating memories they would cherish for a lifetime.

A proud graduate of the University of Virginia (Commerce ’74), Stocky was a devoted Wahoo through and through. Whether cheering on UVA athletics or enjoying the Charlottesville community, his affection for his alma mater never faded.

Music was another lifelong passion. He played both guitar and drums, and his musical adventures began in grade school as the drummer for The Lost World, a band that entertained neighborhood friends. His love of music remained with him throughout his life and was passed along to his three sons, who developed their own appreciation for playing instruments and enjoying live concerts.

Stocky enjoyed a long and rewarding career as a Certified Public Accountant and financial executive, serving in leadership roles including Controller and Chief Financial Officer. He took great pride in his profession and the many relationships he built throughout his career.

Above all, Stocky will be remembered as a true Virginia gentleman — kind, caring, gracious, and full of life. He cherished the camaraderie of family and friends and was never happier than when surrounded by the laughter of those he loved. Together with Rose, he built a life rich in love, family, friendship, and shared memories. His three grandchildren held a particularly special place in his heart, and he delighted in every opportunity to dote on them.

His warmth, friendship, and love of life will be profoundly missed by all who knew him.

A Celebration of Life will be held on Thursday, October 15, 2026, at 1:00 p.m. at St. John’s Episcopal Church, 100 W. Queens Way, Hampton, Virginia, with the Rev. Lisa Erdeljon officiating. A private family interment of ashes at St. John’s Cemetery will follow the service. Friends and extended family are invited to proceed directly to the Hampton Yacht Club, 4707 Victoria Boulevard, Hampton, for a reception following the service. The family will join them after the private interment.

The family extends heartfelt thanks to Yvonne Bailey for her kindness and companionship as a private caregiver, to the compassionate staff of Heartland Hospice, and to LaShawn Smith and her dedicated private caregiving team for their loving care and support. Special gratitude goes to the family members whose love and care meant so much throughout Stocky’s illness.

In lieu of flowers, memorial contributions may be made in Stocky’s memory to Peake Childhood Center at www.peakecc.org or to a charity of your choice.

Arrangements are being handled by R. Hayden Smith Funeral Home in Hampton.