Wine Down Weekend in Charlottesville

Rich in natural beauty, Charlottesville is nestled in the eastern foothills of the Blue Ridge Mountains. The region’s spectacular scenery would be reason enough to make the drive, three and a half hours north of the Triangle.

Drive Time

From Holly Springs: 3 hours, 40 minutes

From Fuquay-Varina: 3 hours, 50 minutes

But along with gorgeous mountain views, visitors will find world-renowned historic sites, hiking trails, orchards and farms, farm-to-table cuisine, and more than 40 wineries, ready to welcome you for a lazy weekend.


Virginia is one of the country’s top wine-producing states, and the wine industry around Charlottesville has exploded in the last 20 years. Wines from Virginia grapes will often taste different from wines produced elsewhere, but exploring that variety is part of the fun and adventure.

Veritas Vineyard & Winery boasts award-winning wins and beautiful mountain views.

A good place to start is the Monticello Wine Trail, consisting of 40 wineries, all within 25 miles of Charlottesville. Stephen Barnard, president of the marketing partnership, is also the winemaker at Keswick Vineyards.

“I would say we’re not in the wine industry; we’re in the hospitality business,” he said. “The winemakers are all committed to promoting the state, promoting the quality and the marketing of the state, yet we still have our own identities. We’re all unique.”

Stephen Barnard, winemaker at Keswick Vineyards

Virginia winemakers take advantage of the grapes that grow best in the region, and Barnard says even familiar varieties might taste a bit different from their California counterparts.

“The climate really gives you wines that are a bit more acidic, (rather) than ripe and opulent,” he said. “It’s because we don’t have the heat; we don’t have the dryness.”

Try a tasting flight at Valley Road Vineyards

Keswick is known for its Cabernet Sauvignon and its Cabernet Franc, a medium-bodied red wine. Worth trying as well is the vineyard’s Chardonnay, a brighter, lighter interpretation well suited to spring sipping.

The folks at Veritas Vineyard & Winery are all about the experience. Andrew and Patricia Hudson bought the scenic 55-acre property in the late ‘90s, and today, their distinctive wines are only part of the package.

Cheese & charcuterie board at Veritas Vineyard & Winery

“We’ve got a couple of award-winning wines that are single varietals,” said Lindsey Navin, marketing manager at Veritas, describing the winery’s Cabernet Franc 2017 Reserve and the 2017 Petit Verdot. “Those two wines, they’re also very much of Virginia grapes. You don’t find those single varietals anywhere.”

About a dozen wines are available in the tasting room, along with cheese and charcuterie boards, salads, sandwiches, and flavorful flatbreads. If you’re hungry for something more, The Farmhouse at Veritas restaurant serves brunch and dinner, with wine pairings from the vineyard. Guests can also spend the night at the six-bedroom bed and breakfast or two-bedroom cottage located on the property.


No trip to Charlottesville would be complete without a visit to the home of Thomas Jefferson, author of the Declaration of Independence and the third president of the U.S. The house and surroundings are beautiful, and it’s easy to see why Jefferson situated his house high on the mountain.

At Monticello, “Thomas Jefferson” shares details about life as the third U.S. president and author of The Declaration of Independence.

Monticello is furnished as it was in Jefferson’s retirement, when he lived there for 17 years before his death. Inventions like the dumbwaiter and his polygraph, an early copy machine, are on display, along with his books and many souvenirs from his travels. Evidence of Jefferson’s inquisitive mind can also be seen in the gardens, where he experimented with ornamental and useful plants from around the world.

Since 2015, several exhibits have opened that describe life at Monticello more completely, beginning with the restoration of workshops and 20 dwellings used by enslaved indentured servants, both Black and white. In 2018, The Life of Sally Hemings opened, detailing the life of the enslaved woman who bore the founding father’s children.

Monticello, home of Thomas Jefferson, showcases his inventions, books and possessions, as well as exhibits describing the life of the enslaved and indentured servants who lived there.

Thousands of visitors tour Monticello each year to learn about Jefferson’s legacy and his complicated history. Most spend at least three hours exploring the expansive estate.

IX Art Park & The Looking Glass

Families with children (of all ages) shouldn’t miss The Looking Glass, an interactive art museum which opened in January 2020. More than a dozen artists collaborated to create a 3,000-square-foot enchanted forest. Last year, the museum doubled in size to 6,000 square feet.

Part of CHarlottesville’s IX Art Park, The Looking Glass is an interactive enchanted forest created by a team of a dozen artists.

Visitors enter through a curio shop lobby, filled with a jumble of trinkets and tchotchkes. A large door-sized mirror is tucked into one corner. “The idea is that it’s your classic portal fantasy — Narnia, Alice in Wonderland, Wizard of Oz — where you’re coming into a curio shop, and there’s this Looking Glass,” said Danielle Bricker, Marketing manager at IX Art Park.

It’s a family friendly, but not a kids-only space. Some of the multimedia exhibits are low to the ground for children to discover; others are at adult height.

“We did not expect this to be an attraction that people became regulars in,” said Bricker. “It kind of felt like, ‘Once you’ve seen it, you’ve seen it.’ But especially with families, we get a lot of repeat visitors.”

IX Art Park hosts concerts and events aimed at making art accessible every day.

The museum is located in the IX Art Park. The former site of the Frank Ix & Sons Textile Factory was transformed into an open-air event space and became a nonprofit in 2019. Its mission is “to make art in all its forms a daily reality for everyone.”

More than 250 events a year are held there, including free outdoor concerts, salsa dance lessons, a farmers market, theater performances and more. Even when nothing formal is planned, visitors can grab a bucket of chalk or an art kit with paper, brushes and paints.

Food and More

Adjacent to the IX Art Park is Three Notch’d Craft Kitchen & Brewery, serving up craft beer and “a locally sourced, beer-infused menu.” Stop in for elevated pub fare or seek out one of the many independent restaurants nearby. Whether it’s Turkish fare from Sultan Kebab, Mediterranean from Orzo Kitchen & Wine Bar, or Southern staples from The Whiskey Jar, you won’t be disappointed.

The downtown mall pedestrian shopping district

“The quality of the food and the sheer number of restaurants that we have just make this a really incredible food destination,” said Brantley Ussery, marketing director for Albemarle County.

The food, culture, history and, yes, the wineries make Charlottesville, a city of 50,000 or so, a destination that, as Ussery puts it, “punches above its weight.”

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