Upper Shirley Vineyard is located on Shirley Plantation Road in Charles City, on the north bank of the James River, roughly 30 minutes from each of Richmond and Williamsburg. The winery sits next to Shirley Plantation, started in 1613 and today the oldest working farm in America. Tayloe and Suzy Dameron opened this large and luxurious winery in 2015, after planting the 16-acre vineyard in 2013. Neither owner has a background in wines, and they hired star Virginia winemaker Michael Shaps to handle this end.
Wine. Among the Top 100 wineries in Virginia. Upper Shirley wines were a big success at the 2024 annual Virginia Governor’s Cup state-wide wine competition, coming away with three gold medals: for the 2018 vintage “Zachariah” (a Petit Verdot, Merlot and Tannat blend), 2020 Chardonnay and 2021 Viognier. At the 2025 Governor’s Cup, three Upper Shirley entries received silver medals: their 2018 Tannat, 2022 “Divertido” (a red wine made from the unusual for Virginia Mourvèdre grape), and 2022 Viognier. Grapes are grown either at the vineyard here, or in an associated vineyard in the Piedmont.
Setting. Two stars. Upper Shirley has an impressive Low Country-style tasting room. The inside is 14,000 square feet circling a fireplace, and tall story windows bring in plenty of light. The also very long shaded front porch looks out onto the vineyard, while sweeping views of the James River and the nearby Presquile Wildlife Refuge are available from the veranda behind the winery. In normal circumstances there is an on-site dining space with an executive chef, a full seasonal menu of lunch items, including starters, salads, and small plates, and dinner available periodically. Under COVID restrictions this is presently limited to picnic offerings. The venue is also occasionally booked for weddings.
Stories. Berkeley Plantation. Five miles from Upper Shirley, around the bend in the James River, lies Berkeley Plantation – the ancestral home of two Presidents of the United States. Berkeley Plantation was originally part of the “Berkeley Hundred,” settled in 1619 by a group of 38 englishmen, shortly after Jamestown. In the early 18th century the Harrison family purchased the 1,000-acre plantation, and in 1726 Benjamin Harrison IV built one of the first multistory brick mansions in Virginia on the hill overlooking the James. His son, Benjamin Harrison V, born on the Plantation, was a signer of the Declaration of Independence and a Governor of Virginia. William Henry Harrison, also born at Berkeley Plantation and son of Benjamin V, became a war hero by winning the Battle of Tippecanoe in 1811, and rode his popularity to become the 9th President of the United States. Until the inauguration of Ronald Reagan in 1981, Harrison had been the oldest man ever to assume the Presidency, though he died only 31 days into his term, from typhoid fever, making him the shortest-serving of all US Presidents. William Henry’s grandson, also named Benjamin Harrison (1833-1901), was elected in 1888 as the 23rd President of the United States. Benjamin Harrison V is buried in the small cemetery on the property. Berkeley Plantation fell into disrepair in the 1800s, and lumber tycoon John Jamieson bought the estate in 1907; the Jamieson family expended large sums in restoring the Plantation and the original mansion. In the 1960s the Plantation was turned into a museum, and is now a popular attraction for tourists around the world to experience the Plantation Era in Virginia. The architecture is original, and the house has been filled with antique furniture and furnishings that date from the period when it was built. The grounds, too, have been restored, and cuttings from the boxwood gardens are available as living souvenirs for its visitors. Berkeley is still a working farm; corn, soybeans, wheat, tomatoes, and other vegetables are grown here. Enthusiastic guides in period costumes conduct tours of the mansion daily. The mansion is furnished with a magnificent collection of 18th century antiques and artifacts. Grounds tours are self-guided and include five terraces of boxwood and flowering gardens leading to the James River. One additional historical note: Berkeley Plantation was occupied by the Union Army during the Civil War, and here in July 1862 the bugle call “Taps” was reportedly played for the first time.