Winter Calvert Cullen III


Mr. Winter Calvert Cullen III, 84, loving husband, father, grandfather, great-grandfather, and Eastern Shore icon, passed away Thursday, Nov. 11, 2021, with his family at his side. The grandson of the late William B. Mapp and the late Mary Rogers Mapp, Winter was born June 14, 1937, at the family home in Mappsburg.

Never one to do anything halfway, Winter always went the extra mile in every aspect of his life. A Hokie through and through, Winter received his Bachelor of Science degree in agricultural economics from Virginia Tech in 1960. That same year he returned home to the Eastern Shore and married the love of his life, Mary Thom Windsor, on Sept. 17. Over the next several years, he worked on the family farm by day and officiated local high school football games by night. In 1965, Winter assumed full responsibility of the farm, successfully operating “Winmar Farms” until his retirement in 1993. In retirement he represented two of his greatest passions, working part time for the Virginia Tech Eastern Shore Agricultural Research and Extension Center for nearly two decades.

Winter was a 32-year member of the Agricultural Stabilization and Conservation Service (ASCS), now known as USDA Farm Service Agency, and an 18-year member of the Virginia Soybean Association Market Development Foundation, serving two terms as president and two terms on the board of directors. During his time with VSA, he was one of 35 selected to travel to Belgium, Iran, and Egypt to introduce and encourage the purchase of American soybeans. He was a lifetime member of Painter-Garrisons United Methodist Church, the Loyal Order of the Moose #683, and the National Rifle Association, as well as past member of both Little Pungo Ruritan Club and the Eastern Shore Jaycees.

A life well lived, Winter believed in working hard and playing hard. As the first person to catch a blue marlin on a private boat out of Wachapreague, he was an offshore fishing legend. If you were aboard the Soybean II, you could guarantee he was going to put you on the fish. He enjoyed going clamming, and he loved hunting … pretty much anything.

Winter rarely missed an auction and folks always knew they didn’t stand a chance at taking home any Eastern Shore relics or memorabilia if he was on the front row. He loved dogs and from the time he was young, you’d rarely see him without his best bud, most recently, his yellow lab, Patton.

Those who were fortunate enough to listen to the master storyteller, spend a day on the ocean or in the woods, cheer alongside him at a Hokie game, or share a meal and a laugh, knew a man of incredible character – the last of a dying breed. Rest in peace, “Sport.”

In addition to his wife of 61 years, he is survived by his children, W. Calvert Cullen IV (Mary Jane), of Wellington, Fla., Kathy Cullen Henley, of Painter, and William Mapp Cullen (Jody), of Keller; grandchildren, Winter C. Cullen V, of Nashville, Tenn., Kristen P. Cullen, of Charlotte, N.C., Lacy V. Henley, of Williamsburg, Va., Savannah L. Henley, of Bristow, Va., Gina C. Ames (Tyler), of Melfa, and Dana C. Sexauer (Matthew), of Dalzwell, S.C.; great-granddaughters, Summer E. Ames, Carsyn F. Ames, Mattison J. Sexauer, Claire M. Sexauer, and his first great-grandson, Tyler Ames Jr., who is expected in December; nieces and nephews, Hal Floyd, Elizabeth M. Spencer, Sheila B. England, and Robert, Thomas, Terry, and David Windsor.

Funeral services were conducted from the chapel of the Williams-Onancock Funeral Home on Sunday, Nov. 14, 2021, at 1 p.m., with the Rev. Carrie Talbott officiating. Private interment followed in the Fairview Lawn Cemetery.

Contributions in Winter’s memory may be made to Painter-Garrisons United Methodist Church, P.O. Box 502, Painter, VA 23420, Eastern Shore Virginia Tech Alumni Association (ESVTAA), c/o Hunter Blake, 15044 Par Place, Melfa, VA 23410, or to Peninsula Tractor Organization, 8104 Sunset Cove Drive, Exmore, VA 23350 (

Memory tributes may be shared with the family at

Arrangements were by the Williams-Onancock Funeral Home.
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