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Virginia's Horse and Wine Country

Photo: Baerbel Schmidt

In Washington, D.C., the jockeying is all political, but drive some 50 miles south and you’ll find the real thing, in the heart of Virginia’s horse country. Ever since Thomas Jefferson built Monticello here, the pastoral foothills of the Blue Ridge Mountains have been a sporting ground for a certain class of power players—folks like the Mellons, Harrimans, Grahams, Jackie Kennedy—coming down to weekend with their thoroughbreds and beagles. The region’s social calendar still revolves around the International Gold Cup and Virginia Gold Cup steeplechases, run every October and May, respectively, on vast, impossibly green rolling plains. A newer attraction is the burgeoning winery scene. Head south past countless horse farms to Charlottesville, and you encounter some of the state’s best chefs and best bottles.

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Our Picks

3 Hotels 5 Restaurants 8 Activities

Destinations: Virginia · Middleburg · Washington · Charlottesville · Barboursville

Themes: Road Trip · Food + Drink · Adventure

Inspired by: Virginia Unbridled — by Matt Lee, Published Aug. 2007

Hotels (3)

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Red Fox Inn

Middleburg | U.S. + Canada | U.S. | Virginia | Washington, D.C. | Washington D.C. Suburbs

Spacious rooms in the heart of downtown Middleburg.
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Keswick Hall

Charlottesville | U.S. + Canada | U.S. | Virginia | The Charlottesville Area | Shenandoah + The Blue Ridge Mountains

The foothills of Virginia’s Blue Ridge Mountains, south and west of Washington, D.C., are a playground for the city’s old guard, their horses, and the
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Goodstone Inn & Estate

Middleburg | U.S. + Canada | U.S. | Virginia | Washington, D.C. | Washington D.C. Suburbs

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Restaurants (5)

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Market Salamander

Middleburg | U.S. + Canada | U.S. | Virginia | Washington, D.C. | Washington D.C. Suburbs

Stop in for fried-chicken box lunches.
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Coach Stop Restaurant

Middleburg | U.S. + Canada | U.S. | Virginia | Washington, D.C. | Washington D.C. Suburbs

A classic neighborhood diner.
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Ashby Inn & Restaurant

Middleburg | U.S. + Canada | U.S. | Virginia | Washington, D.C. | Washington D.C. Suburbs

Located at the foot of the Blue Ridge Mountains just an hour west of D.C., the 1829 Ashby Inn is home to an acclaimed New American restaurant serving
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The Clifton Inn Restaurant

Charlottesville | U.S. + Canada | U.S. | Virginia | The Charlottesville Area | Shenandoah + The Blue Ridge Mountains

At the intimate Clifton Inn, the decadent rusticity of the rooms—claw-foot tubs, Mascioni linens, fireplaces, but nary a ruffled window treatment in s
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Palladio

Barboursville | U.S. + Canada | U.S. | Virginia | The Charlottesville Area | Shenandoah + The Blue Ridge Mountains

Virginia is one of the country’s fastest-growing wine regions, and Palladio is one of the best restaurants in the state—it’s built on the grounds of a
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1 - 5 of 5 Results

Activities (8)

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American in Paris

Virginia | U.S. + Canada | U.S.

Owners Carol and Gary Konkel share 20 years experience and a discerning eye for mid-18th to mid-19th century American antiques with a specialty in Ame
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Gold Cup

Virginia | U.S. + Canada | U.S.

The most festive time to visit Virginia's horse country is during Gold Cup race weekends, which happen in October and May every year.
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Monticello

Charlottesville | U.S. + Canada | U.S. | Virginia | The Charlottesville Area | Shenandoah + The Blue Ridge Mountains

in 1770, Jefferson sold some of the land surrounding Monticello, his sprawling Palladian home up in the hills just outside Charlottesville, to an Ital
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Kluge Estate Farm Shop

Charlottesville | U.S. + Canada | U.S. | Virginia | The Charlottesville Area | Shenandoah + The Blue Ridge Mountains

Patricia Kluge, an heiress and philanthropist, entered Virginia's wine game in 1999, and the estate was initially dismissed by many critics as a lark
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Gadino Cellars

Washington | U.S. + Canada | U.S. | Virginia | The Shenandoah Area | Shenandoah + The Blue Ridge Mountains

Located in Rappahannock County, Virginia, this small, family-run vineyard was founded in 2004. Owned by Bill and Aleta Saccuta Gadino, who began makin
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Chrysalis Vineyards

Middleburg | U.S. + Canada | U.S. | Virginia | Washington, D.C. | Washington D.C. Suburbs

At Chrysalis, a winery founded in 1997 with the mandate to make the Norton, Virginia's native grape, viable for wine production, visitors are encourag
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C&O Bar

Charlottesville | U.S. + Canada | U.S. | Virginia | The Charlottesville Area | Shenandoah + The Blue Ridge Mountains

A dimly lit college watering hole.
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Blue Ridge Parkway

Virginia | U.S. + Canada | U.S.

While the masses descend on the North Carolina portion of the famed 469-mile-long parkway, those in the know head to this 121-mile portion from Waynes
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Similar Trips (3)

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Guide to Asheville, NC

Virginia, Asheville

Encircled by the rolling Blue Ridge Mountains, and a five-minute drive from the bucolic Blue Ridge Parkway, the North Carolina town of Asheville has been drawing travelers in search of a holistic holi
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Driving Southwestern Virginia's Mountains

Virginia, Floyd

On the southern outskirts of Roanoke, the slightly down-and-out atmosphere of pawnshops and converted industrial buildings gives way to a more pruned, suburban feel. Then after an innocuous-looking tu
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Touring Virginia's Vineyards

Virginia, Washington, Charlottesville, Barboursville

After 200 years of trying, Virginia's wines are finally worthy of consideration…and with well-appointed inns and B&B’s at every turn and multitudes of historical markers, wine-touring here makes perfe
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Virginia's Horse and Wine Country

Our Picks

Hotels (3)

Restaurants (5)

Activities (8)

Similar Trips (3)

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