7 Stunning Wineries Near Winston-Salem

When successful Wall Street hedge-fund manager Jay Raffaldini decided to open a winery, he could have done so anywhere, yet he opted for the rolling hills and temperate climate of the Yadkin Valley. That’s where he built a breathtaking Tuscan-style villa and planted his first vine in 2001, soon becoming the award-winning Raffaldini Vineyards. The rocky soil and warm climate are perfect for producing classic Italian varietals, earning the winery the nickname “Chianti in the Carolinas.”

Established in 2010, Piccione (pronounced Pitch-oo-nee) is highlighted by Italian-style wines paired with postcard-worthy views and a stunning tasting room that opened in 2023. The scenery at Piccione is truly second to none, as the winery takes full advantage of its setting atop a high ridge, offering 360-degree vistas across the Yadkin Valley to the Blue Ridge Mountains.

Founded by NASCAR legend and Winston-Salem native Richard Childress, Childress Vineyards is home to one of the Top 25 tasting rooms in America (per Wine Enthusiast). The Tuscan-inspired space sits at the center of a picturesque 100-acre property in the neighboring town of Lexington, NC, less than 20 minutes south of downtown Winston-Salem. In addition to the award-winning wines and vineyard tours, guests can grab a bite at Childress' onsite restaurant, The Bistro, recently named to OpenTable’s top 100 most scenic restaurants in America list.

With stunning views of nearby Pilot Mountain and Cox Lake, Jolo Winery & Vineyards exudes charm at every turn. Enjoy your tasting flight in the mountain lodge-esque tasting room, complete with stone fireplaces. The onsite restaurant, End Posts, was voted one of the top 100 brunch spots in America by OpenTable and features a full lunch and dinner menu.

Brothers Charlie and Ed Shelton founded Shelton Vineyards in 1999 in an area once dependent on tobacco farming. At the time, North Carolina was home to fewer than ten vineyards. Today, Shelton is the state’s largest family-owned estate winery with 25,000 cases produced annually. Spanning 406 serene acres, there are plenty of scenic spots to enjoy your wine here, including several picnic tables along with the walking path that winds around the lake. Another great place is Shelton’s on-site bistro-style Harvest Grill, which is adjacent to the winery and open daily for lunch and dinner (including Sunday brunch)

Encompassing 1,500 acres, this high-end, high-altitude winery yields bold Bordeaux varietals. A long, winding driveway leads to the Dynamis Estate, set amid rolling green fields and lush orchards in the shadow of the Brushy Mountains. The property includes four distinct vineyards and six acres of fruit and pecan orchards. Casual tastings with small bites are offered along with in-depth, sit-down experiences.

Nestled on 91 acres in the Yadkin County town of East Bend, NC — less than 30 minutes from downtown Winston-Salem — this unique vineyard and tasting room just happens to be on the Southeast’s largest llama farm. Grab a bottle of wine or sit down for a tasting flight, then visit with the llamas! You can even sign up for a llama trek, a 2.5-mile scenic hike with llamas that ambles through rolling hills and alongside a creek.