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Nelsen Williamsburg

OBITUARY

Henry Winston Shepherd Jr.

February 27, 1956June 15, 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.

Services

No public services are scheduled at this time. Receive a notification when services are updated.

Memories

Henry Winston Shepherd Jr.

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Ann and Doug McGibbon

July 22, 2021

My parents (Pat and Bruce Bolding) were very close to the Shepherd family, and the Shepherds were part of my growing up in Williamsburg. We are so glad Win was able to join some of our family celebrations in recent years. He was kind, and we certainly enjoyed our time together. Now they are cherished memories and we are thankful to have them. He will be truly missed.

Ann and Doug McGibbon

Patricia Bolding

July 22, 2021

WIN'S PARENTS . BARBARA AND WINSTON WERE LONG TIME FRIENDS OF OURS. MY SONS WERE IN BOY SCOUTS WITH WIN. WIN KEPT IN TOUCH WITH US EVEN AFTER HIS PARENTS' PASSING. JUST FOUND OUT TODAY (7/23) ABOUT HIS PASSING AND AM SO SORRY TO HEAR.
PAT AND BRUCE BOLDING

Frank Volpicella

June 28, 2021

I worked with Winston at WTSP-TV Tampa/St. Pete in the mid 80's. We spoke weekly these last few years--he was in good spirits--sure a bit ornery at times--but always quick with a funny story or a laugh.
He was one of the finest directors I've ever worked with. He also was an avid sailor. I had the pleasure of sailing with him around Tampa Bay many years ago. Winston loved sailing and we often talked about his desire to return to the waters. I do hope that somewhere, Winston is behind the wheel of a 40 foot sailboat navigating stormy seas. He'd be at peace that way.
He was a dear friend who will be greatly missed.
Frank Volpicella
Tulsa Ok.

FROM THE FAMILY
FROM THE FAMILY