Wines and Equines—D.C.’s Wine Country | Middleburg | Virginia / by Brian Yost

The Red Fox Inn is the nations oldest continually operating inn.

The Red Fox Inn is the nations oldest continually operating inn.

Driving west on Route 50 from Washington D.C., you will first encounter the suburban sprawl of Northern Virginia. After passing through Chantilly, however, the landscape begins to transition from urban to rural.  As you near the village of Aldie, the transformation is complete.  You will begin to see winery signs. Old colonial and post-colonial brick and stone houses pepper the route and large horse farms line both sides of the road. You have entered a region that is known as both the “Nation’s Horse and Hunt Capital” and “D.C.’s Wine Country.”

The “horse and hunt capital” designation refers specifically to a wider array of equestrian sports. Along with the many horse farms, you will find polo fields and equestrian eventing facilities throughout the region. Fox hunting is a major sport and hunt clubs are headquartered throughout the surrounding counties.

The “wine country” moniker is an obvious reference. Although I find the description inaccurate, it is a region frequently referred to by travel writers as “the next Napa.” It is certainly an area that is ripe for wine tourism, but it does not necessarily aspire to be “Napa-like.” After you visit, I think you will agree that the local charm is unique to a part of the United States that offers much more than just wine.


Further along Route 50 and at the heart of the region, you will enter the town of Middleburg. It was established in 1787 as a halfway point between Alexandria and the frontier settlement of Winchester. The Red Fox Inn, America’s oldest continually operating inn is located on Washington Street, which is the town’s main thoroughfare.  Opened in 1728 as a stopping point for travelers, it is actually older than the town that surrounds it. The inn is the most famous landmark, but the town and local countryside are dotted with many historic colonial and Federal-style buildings. 


In addition to being of historic significance, the town is an excellent base for exploring the local wineries and other points of interest. At the end of the day, you should plan on returning to Middleburg for its dining, lodging and entertainment options. 

The Middleburg AVA (American Viticultural Area)

Loudoun and Fauquier Counties, in north-central Virginia, make up the area of fastest growth for the Virginia wine industry. At last count, there were roughly sixty wineries in that pair of rural counties. Cutting through them, like a lazy letter “J,” is the Middleburg AVA. It takes its name, of course, from the town of Middleburg, which sits in the heart of the viticultural area.

The AVA is quickly becoming famous for the quality of wine produced. There is still a great deal of experimentation with different varietals. Viognier, Chardonnay and Vidal Blanc are among the most common whites. Most of the Bordeaux varietals do well and make some powerful and memorable blends, but Cabernet Franc gets my vote as best single-varietal red. Finally, I should mention Norton, an American hybrid that is grown in the eastern half of the United States. It can produce big, cellar-worthy wines, but wine drinkers tend to either love it or hate it.  Of course, these are just a few of the local offerings. 

Nearby Wineries

There are several wineries within minutes of Middleburg, but there are three of particular note that you will want to make an effort to visit. Each offers something a little different and together they provide a view of the range of possibilities the region offers.

Boxwood Estate Winery is just minutes south of Middleburg. It is a winery that specializes in Bordeaux blends. Hugh Newell Jacobsen designed the tasting room and winery. His use of linear design and open space resulted in one of the most striking and modern winery buildings in Virginia. This alone is a reason to visit, but the wines are equally spectacular.

West of Middleburg and just off of Route 50, you will find Greenhill Winery and Vineyards. It occupies a stunning setting that offers views of the distant Blue Ridge and sunsets from its veranda or lawn. At the back of the property, there is a fully restored eighteenth-century farmhouse reserved for the wine club and special events, but worth checking out. The wines of note include a sparkling Blanc de Blanc, Syrah and Bordeaux blend.

A little further west and just outside the village of Aldie, you will find Chrysalis Vineyards. The 209-acre Locksley Estate is a sprawling property surrounded by low hills and countryside and an ideal spot to linger. They specialize in French and Spanish varietals, but owner Jennifer McCloud is possibly the world’s biggest proponent of the Norton grape. Nearly forty acres are devoted to the hybrid, which makes them the largest grower on the planet. They also produce some of the best Norton you will find anywhere, so if you are interested in tasting it, Chrysalis should be one of your stops.

Equestrian Tradition

Long before there were wineries in Middleburg, the town was recognized as the Nation’s Horse and Hunt Capital. Thoroughbreds are raised on farms surrounding Middleburg. Just north of town, you will find the equestrian eventing facility at Glenwood Park. You can also catch a polo match at the Virginia International Polo Club a few miles west of town or just minutes east at Banbury Cross and these are only a few of the local venues.

Middleburg is also home to the National Sporting Library and Museum. Since 1954, the museum has been celebrating field sports, angling and equestrian events. A permanent art collection, in addition to special exhibitions, is open to the general public. Even if this is not quite your cup of tea, I think you will still be impressed by the exhibits and the museum grounds. 

Inns and places to dine

Do not expect to find fast food restaurants in Middleburg. If that is what you are in the mood for, you need to drive back to Chantilly or up to Leesburg. You should plan to sit down at one of the local establishments or organize a picnic, which can be enjoyed at one of the local wineries. Life is a little slower in Middleburg and that is part of the small-town charm. 

Dining options range from pub fair at the Red Horse Tavern at the western end of Washington Street to Julien’s French dining at the other end of town. There are numerous options in between and you will find some of those listed below.

In my opinion, the local inns are the main event for dining and offer the only real options for lodging. Of course the historic charm of the Red Fox Inn place this high on any visitor’s list.  The romantic accommodations retain their eighteenth-century charm. Red Fox also offers first-rate dining and one of the best local Sunday brunch menus in town.

More upscale accommodations and the very best of local dining will be found at the Goodstone Inn. Located on a 265-acre estate ten minutes north of Middleburg, Goodstone offers the finest luxury lodging, a fine dining experience and a full range of amenities. The grounds and surrounding countryside are absolutely serene and breathtakingly beautiful. 

Other points of interest

Breweries, distilleries and cideries are spread through the surrounding counties. The northern entrance to the Shenandoah National Park is about thirty minutes away and the area is full of Civil War battlefields.  Bike trails wind through the region and just across the mountains, in Front Royal, you will find the nation’s canoeing capital and access to paddling the Shenandoah and Potomac Rivers.

Getting there

Due to the rural location, automobile is the most sensible mode of transportation. Here are some average driving times:

Dulles International Airport - 30 minutes | Washington D.C - 1 hour

Baltimore - 1 hour, 30 minutes

Philadelphia - 3 hours

New York - 4 hours, 30 minutes

Nearby Wineries

Boxwood Estate Winery

2042 Burrland Rd., Middleburg


Cana Vineyards and Winery

38600 John Mosby Hwy., Middleburg


Chrysalis Vineyards

23876 Champe Ford Rd., Middleburg


Greenhill Winery and Vineyards

3595  Winery Ln., Middleburg


Quatro Goombas

22860 James Monroe Hwy., Aldie


Other nearby points of interest

Aldi Mill: Virginia's only surviving grist mill

Mount Zion Church Historic Park

National Sporting Library and Museum

Shenandoah National Park

Smithsonian National Air and Space Museum