When Werten Bellamy first arrived at Great Oak Manor in the middle of the night, he had his doubts about the fading guesthouse’s prospects. “Honey, nobody’s going to come here,” he told his wife, Kellye Walker. Then he awoke the next morning in a room facing the sparkling Chesapeake Bay and had a change of heart. The property sits just outside Chestertown, part of a 1659 land grant that covered some two thousand acres. The handsome neoclassical brick manor home arose in 1938 and later became a sportsman’s retreat for the businessman Frank Russell, who hosted such luminaries as Ernest Hemingway, Arthur Godfrey, and John F. Kennedy. Russell offered hunting, fishing, horseback riding, an illegal casino, and the seclusion that his famous guests sought. Since purchasing the spread in 2022, Bellamy and Walker have renovated the common areas and guest rooms and are planning to start construction on a demonstration kitchen. A notable addition: Area artisan Vicco von Voss crafted a bar from an on-site black walnut tree. It’ll be the perfect gathering spot come January 10–12, when the property hosts From Napa to Italy: A Wine and Food Experience with the acclaimed sommelier Haley Moore, the first event of 2025’s Taste of Great Oak Manor monthly culinary series.
Southern Agenda