Wining and Dining in Charlottesville, VA

Home to the Monticello Wine Trail with dozens of wineries, the Charlottesville area is an oenophile’s dream

As a traveler who loves wine, I’m driving to Charlottesville on this late-September day to visit Virginia’s wine and culinary capital. The sun’s rays peek over the horizon, lighting the golden fields and wildflowers that flank undulating country roads. In the last 10 miles, I’ve passed a dozen signs for vineyards that point toward long driveways. I make a mental note to check out some of them on my way home.

Wine is, of course, dependent on soil, weather and topography, or terroir. Annette Ringwood Boyd, director of the Virginia Wine Board, describes this area’s wines as more fruit forward and not as “jammy” as West Coast wines. “They tend to have higher natural acidity,” she says. More than half of Virginia’s vineyard acres grow within the Monticello American Viticultural Area. Currently, there are 43 member wineries on the Monticello Wine Trail, all within 25 miles of Charlottesville—an oenophile’s dream destination.

To help plan my itinerary, I consulted, the website of the trail named for the home of Charlottesville’s former resident Thomas Jefferson. More than 200 years ago, our third president attempted to grow grapes here.


There’s no more intriguing place to dine than Charlottesville’s Dairy Market. Built in 1937, the original market sold ice cream, milk and eggs. The building reopened in December 2020 as a vibrant food hall.

As we walk through the market, Anna Payne, director of marketing, lists a world of options: “We have 17 vendors, including Filipino food, tacos, ramen, vegan fare, burgers, and ice cream from MooThru. We have a bar called Milkman’s, and there’s Starr Hill Brewery.”

After much deliberation (and salivation), I order lunch from Angelic’s Kitchen, a soul food eatery known for its fried fish. The crispy whiting comes with two sides, so I choose tangy collard greens and mac and cheese.

While I’m eating, I notice students from the University of Virginia sitting alongside families, seniors and workers on their lunch break. I comment that Dairy Market feels like a community unto itself. Payne agrees, “We have changed the way Charlottesville goes out.”

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