Starting a winery isn’t for the faint of heart—and David Sheldon, owner of Hampton Roads Winery in Surry County, Virginia, knows that better than anyone. After 25 years running a plastics factory in Massachusetts, David and his wife, Diane—a research chemist—decided to retire into something they both loved: wine. What they didn’t realize at the time was that their “retirement project” would become a full-blown adventure filled with heat, hurricanes, high humidity, and a few “Green Acres” moments along the way.
Their journey—and all its triumphs and tribulations—is chronicled in David’s engaging new book, You Can Wine Too, a must-read for anyone who has ever dreamed of starting a winery from scratch.
Finding a Home—and Learning the Hard Way
When David and Diane traded snowy Massachusetts for the warmer climate of coastal Virginia, they imagined a longer growing season and an idyllic life among the vines. What they found instead was humidity, challenging soils, and a crash course in viticulture.
“We thought Virginia would have a longer growing season—and we were dead wrong,” David said with a laugh. “The heat and humidity determine when we pick. And hurricanes do too!”
Armed with advice from Virginia Tech’s viticulture program and a lot of determination, the Sheldons planted their first vineyard on less-than-ideal land: flat, poorly drained, and heavy with silt. They learned by trial and error which grape varieties could survive the Tidewater region’s extremes—and which couldn’t. Over time, they discovered what truly thrived on their farm, including Norton and Muscadine, two grapes perfectly suited to Virginia’s climate.
A Winery Built on Persistence—and a Little Humor
In the early years, David split his time between Massachusetts and Virginia, commuting back and forth while the vines slowly matured. When harvest finally arrived, the couple faced a new challenge: making wine.
Their first attempt was, as David puts it, “a disaster.” Trying to ferment Norton in an air-conditioned carport under the Virginia sun was, in his words, “like trying to make wine in a sauna.” The heat spoiled the batch, but it also ignited a new sense of purpose. The Sheldons got serious, built a proper winery, and began producing wines that reflected their hard-earned lessons.
That commitment paid off. Hampton Roads Winery is now celebrating its 10th anniversary, producing a range of wines including Norton blends, Vidal Blanc, and their best-selling Hog Island Sweet White, made from Muscadine grapes.
The Tallest Goat Tower in the World (Really!)
Of course, no story about Hampton Roads Winery is complete without mentioning its famous Goat Tower. Inspired by a winery in South Africa, David decided to build one of his own—by hand and with local craftsmen. The result? A four-story brick structure that has become the winery’s signature landmark.
“When people come to visit us, they remember us for the Goat Tower,” he said. “You come for the wine, but you stay for the goats.”
The tower even inspired the winery’s popular Goat Tower wine series, featuring wines like the Goat Tower Chardonnay (a crisp, fruit-forward, unoaked white that perfectly suits Diane’s style as a chemist-turned-winemaker).
From Calves to Cabernet: Farm Life at Its Finest
Hampton Roads Winery isn’t just about grapes—it’s a true farm winery, complete with cattle, goats, and plenty of stories. One of the most touching in David’s book is about “Nicholas,” a calf he rescued on a freezing December night.
“I carried him out of the mud and spent the night on the couch next to him,” David recalled. “For three months I bottle-fed him twice a day. Every time I entered the pasture, he’d come running. Eventually, though, I had to wean him—and I think the other cows warned him not to trust me after that!”
It’s those very human moments that make You Can Wine Too such a compelling read. It’s not just about wine—it’s about perseverance, problem-solving, and the humor required to keep going when things don’t go as planned.
Lessons from the Vineyard
When asked what advice he’d give someone dreaming of starting their own winery, David didn’t hesitate:
“I wish I’d started 20 years sooner,” he said. “Don’t wait until retirement to chase your dream. This business takes time—and marketing is everything.”
Despite being “across the moat” from Virginia’s busier wine regions, Hampton Roads Winery has carved out its own following, drawing visitors from Williamsburg, Virginia Beach, and RV travelers heading south through programs like Harvest Hosts and Good Sam Club.
Visit Hampton Roads Winery
If you’re traveling through Virginia, make a point to stop at Hampton Roads Winery—home to world-class wines, a record-breaking Goat Tower, and a family that turned their dream into reality.
Hampton Roads Winery
3450 New Design Road
Surry, Virginia
📍 hamptonroadswinery.com
You can also find David’s book, You Can Wine Too, on Amazon and Barnes & Noble, or directly through the winery’s website.
Final Sip
As David put it best:
“So often people think they come into a winery, see success, and don’t realize what it took to get there. It’s not for the weak at heart.”
Listen to the full interview on the Uncork Your Mind podcast or watch the webinar for more laughs, lessons, and inspiration straight from the man who proves that yes—you really can wine too.
