Wining and Dining in Virginia’s Best Wine Region

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Photo by Brian Yost

Wine and dine against a historic backdrop in Charlottesville

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History-rich Charlottesville is Virginia’s best wine region and a top foodie destination.

Charlottesville is centrally located with countless lodging opportunities and a range of price points. It also offers many dining and entertainment options. For a slightly more upscale resort environment, consider Keswick Hall. Or opt for a full vineyard experience at the historic Barboursville Vineyards.

Virginia’s Best Wine Region: Charlottesville, Day 1

Check into your lodging mid-afternoon and head out to Barboursville Vineyard and Winery in Orange County, just minutes away. Arrive early to explore the stunning property which contains one of the country’s only true historic ruins and nearly 200 acres of vines.

Dine, with reservations and appropriate dress, at their elegant Paladio Restaurant.

Keswick Hall
The entrance to Keswick Hall.

Charlottesville, Day 2

Keswick Hall is a must-stop for lunch (or Sunday brunch) in the heart of Central Virginia’s horse and hunt country. Reservations are recommended.

It is a five-minute drive from Keswick Hall to Keswick Vineyards, where you can taste some of the state’s most highly-regarded wines and drink in stunning view of the Southwest Mountains.

Travel a little further east to explore Montpelier, a National Historic Landmark once home to James Madison, America’s fourth president. The mansion and 2650-acre property are open daily.

Spend the evening in Charlottesville, bursting with dining options. Check out the recently gentrified Belmont neighborhood, where our favorite tapas and Italian restaurants are located. Other options are within easy walking distance.

Check the Cville Weekly site for music venues and special events, many of which are a short drive downtown to the pedestrian-only mall. Look for free concerts on the eastern end of the mall in the Sprint Pavilion on Friday evenings. Other music venues include the Jefferson Theater and Millers.

Charlottesville, Day 3

For lunch stop by the Corner Restaurant District, just across from University of Virginia. Wander the university grounds; explore the rotunda and adjacent lawn, part of the original university founded in 1819 by Thomas Jefferson.

Take a drive to the notable Jefferson Vineyards, part of an estate once belonging to the third president.

Cap a day of exploring Mr Jefferson with a short drive to Monticello, a National Historic Landmark and UNESCO World Heritage Site. Brush up on history at the visitor’s center before catching a shuttle up to the property.

Main Street, which offers a wide range of options and price points, is another prime Charlottesville restaurant district. Eateries get very busy after 7 pm, so plan accordingly.

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