Henry Winston Shepherd Jr.

1956 - 2021

Henry Winston Shepherd Jr. passed away on June 15, 2021, in Williamsburg, Virginia, after a lengthy illness. Winston is preceded in death by his father, Henry Winston Shepherd; his mother, Barbara S. Ware Shepherd; and his sister, Barbara ("Bobbie") Ware Shepherd. He is survived by his uncle and aunt, Taylor and Carol Ware, and many cousins. Born February 27, 1956, in Richmond, Virginia, Winston lived in many places throughout his life including the Virgin Islands, New York, Florida, and the Midwest. He had a deep connection to Williamsburg, the community that had long been home to his parents and sister and where he spent his formative years. Winston was a man of many interests, accomplishments and abilities. He had a lifelong interest in aviation and valued his connection with the Colonial Virginia Aeromodelers club in Williamsburg, going out to the airfield to fly a variety of remote-controlled model aircraft that he built himself. Above all else, he had a deep love of the water and was a gifted sailor who relished the challenge of mastering all conditions, whether on the Rappahannock River, the Chesapeake Bay, the open ocean or racing on one of the Great Lakes. He once sailed 500 miles from Orlando, Florida to Isla Mujeres, Mexico, navigating successfully through stormy seas with no GPS – just a compass, a chart and a clock. Winston liked to laugh. He had interesting stories to tell and was a good listener of other people's stories. He made many deep friendships throughout his life and experienced the joy of those friendships being renewed during his final illness. He was loved and will be remembered and missed by his friends and family. Winston will be laid to rest at Cedar Grove Cemetery in Williamsburg. Services will be private. Memorial contributions may be made to the Williamsburg Volunteer Fire Department and Rescue Squad, 444 N Boundary St, Williamsburg, VA 23185. Online condolences may be shared at www.nelsenwilliamsburg.com.