Robert Stone Wolcott

Robert Stone Wolcott
November 17, 1943 - December 19, 2025
Robert Stone Wolcott, 82, of Virginia Beach, Virginia, passed away peacefully on December 19, 2025, at Sentara Virginia Beach Hospital, surrounded by his loving family.
Rob was born in West Hartford, CT on November 17, 1943, the youngest of three children of Frank Edward Wolcott II and Rosemary Stone Wolcott. He attended Berkshire Academy for four years and spent his summers working in Nantucket. He graduated from Lafayette College in Pennsylvania in 1961 and soon began his career with Aetna Insurance Company, relocating with the firm to Green Bay, Wisconsin.
Business was often conducted on golf courses and over two-martini lunches in those days. This first position launched a long and successful career in the insurance industry, with professional moves from Philadelphia to New York City, and eventually to Norfolk, Virginia, with The Marsh McLennan Agency. There, Rob provided employee health benefits for CBN, Old Dominion University, and many major hospitals in the area. Disliking the commute from the Oceanfront to Norfolk and facing a pending corporate transfer, he made the bold decision to start his own company, B&W Benefit Planning, from which he later retired.
Rob loved walking the neighborhoods of the North End and riding his bicycle around Virginia Beach. His life was tragically cut short when he was struck by a car less than a half mile from his home. He leaves behind to mourn him his devoted wife of 40 years, Nancy Titus Wolcott; his daughter Elizabeth Hobbs Wolcott (Thomas Quattlebaum); his son Alexander Stone Wolcott (Laura); his stepdaughter Lisa Beck Falvo (Mark); his stepson, Frederick Warren Beck IV; his cherished grandchildren, Annabel Skye Quattlebaum, Juliet Stone Quattlebaum, Jackson Griffith Wolcott, Mabel Stone Wolcott, Parker Elizabeth Kinton, Olivia Annisa Falvo, and Logan Douglas Falvo; and his sister, Toni S. Wolcott. He also leaves behind his good friend and mother of his children, Lana Hobbs Wolcott.
Rob found his greatest joy spending time with his family and friends at Sunday dinners, in his workshop on the latest project or riding his tractor at his farm on the James River in Appomattox County, VA. He was happiest with a fishing rod in hand, whether in the Florida Keys, St. George Island, the James River, or at Lee's Mill Pond.
A lifelong Green Bay Packers fan, Rob proudly attended the legendary Ice Bowl, an experience he loved to recount. In later years, Rob took up woodworking and could often be found in his workshop, carefully crafting bowls, spoons and other handmade gifts for family and friends.
Rob will be remembered for his steady presence, quiet generosity, and deep devotion to his family. He was a man who valued hard work, loyalty, and time spent together. His stories, his craftsmanship, and his unwavering love for his family will be carried forward by all who knew him. He leaves behind a legacy of kindness, integrity, and enduring family bonds.
A Celebration of Life will be held on January 23, 2026, from 3:00 - 5:00 p.m. at the Cavalier Golf and Yacht Club.
In lieu of flowers, donations may be made to the James River Association. Make a Donation - James River Association