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 40 wineries in Virginia. Upper Shirley first made a splash in the 2019 Virginia Governor’s Cup statewide wine competition, as their 2014 Zachariah red blend was named as part the Governor’s Case, the 12 top bottles as voted by the judging panel out of over 500 entries. The Upper Shirley Blanc des Blancs sparkling wine was awarded a gold medal at the 2022 Virginia Governor’s Cup competition, and their 2016 vintage Tannat and “Zachariah” (a Petit Verdot, Merlot and Tannat blend) were awarded gold medals at the 2021 competition. At the 2023 Governor’s Cup event, Upper Shirley wines received four silver medals: for the 2021 Viognier, 2020 Chardonnay, and 2017 vintage Tannat and Zachariah. The 2020 “Divertido” (a red wine made from the unusual for Virginia Mourvèdre grape) received a bronze medal at the event. Several Upper Shirley wines were awarded silver medals at the 2022 Governor’s Cup competition: the 2016 vintage Tannat and Zachariah (both back for an encore after their gold medals of the year before), 2019 Chardonnay, 2020 Viognier and Sparkling Rosé. 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.