Wineries, horse country, and historic towns in a lush English-like countryside are straight out of a fairytale.
Loudoun County, Virginia, is the wealthiest county in the United States, with a median household income of $170,463. It beat out many of the counties you might have expected to top this list, like Silicon Valley’s San Mateo County, California–though that still made the list, at number four.
Located 25 miles outside Washington, D.C, Loudoun County in Northern Virginia is a rich mélange of verdant spaces, lush valley views, cobblestone-lined small towns, outdoor activities, scenic nature, historic towns and villages, a metro tech center, and, of course, wineries. For an adventurous D.C. day trip or a relaxing weekend from ever-bustling Northeast cities, it’s a unique getaway for all travel personality types.
How to Get to Loudoun County
From D.C., Maryland, and Virginia cities, Loudoun County is easily accessible by vehicle or D.C. Metro for the transit-loving travel types. From Northeast cities like NYC, Philadelphia, and Boston, a direct Amtrak train from these hubs to D.C. Union Station, then a Silver Line Metro to the last stop, Ashburn–a commercial center and home to Data Center Alley–will start your Loudoun County adventures. Nevertheless, a vehicle is the ideal transportation mode with which to traverse Loudoun County’s deep towns and villages, especially in the winery countryside. In the larger towns, Uber is available with a 15-minute wait.
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Walkable Historic Towns and Villages
Begin your adventure in Leesburg, the county seat. You’ll need a vehicle to get here (or Uber), and it is a 15-minute ride from Ashburn. Established in 1758, the Town of Leesburg has grown from 1,688 residents in 1850 to almost 50,000 today. Once here, the town is very walkable, and if you squint, you can almost feel transported back in time with its historic brick architecture, small business-lined Main Street, and cobblestone paths.
History nerds will love Leesburg with its many stately homes and historical figures. For example, Dodona Manor is the home of George Marshall–of the famed Marshall Plan that provided economic assistance to Europe after World War Two–and it details his exemplary service from Chief of Staff to Secretary of Defense; Oatlands Historic House and Gardens is on over 300 acres of land with terraced gardens and self-guided tours of its beginning as a wheat-producing plantation economy; Historic Leesburg Walking Tours is ideal for those wanting narration and interesting background on historical architecture, barely known Civil War trivia, and scandalous gossip of bygone eras.
Known as the nation’s horse and hunt capital, Middleburg was established in 1787 and still retains its English architecture and aesthetic. It is solely accessible by car, but the downtown area is very walkable. Start at the historic Red Fox Inn, standing since 1728. It was a frequent haunt of Jackie Kennedy and Elizabeth Taylor, and the inn still possesses thank-you letters that the First Lady sent them. Walk the main street for shops, cafes, and antiques, then take a short drive around the surrounding countryside for stately mansions on acres of green space.
Away from the county’s two famous towns is Lovettsville, founded by Maryland Germans in the 1730s and known as the “German Settlement.” It blends history with modernity as it is known for its Oktoberfest every fall. Lastly, a truly historic town to visit is Waterford, founded by Quakers in 1733. The whole town is on the National Register of Historic Places and feels like a living museum with rustic cabins and stone architecture.
Loudoun County has a long African-American history, going by the number of rehabilitated plantation manors that are now boutique hotels, stately mansions, and historic homes. From Underground Railroad Sites at Leesburg’s Loudoun County Courthouse and Thomas Balch Library to Douglass School, the first African-American high school in the county established in 1941, there is much to be educated on here. In addition, Purcellville, a small Loudoun County town first settled in 1764, boasts of Billy Pierce, an African-American man who established his dance school in New York City, taught Fred Astaire, and helped inspire the Harlem Renaissance.
Gallop into the Horse Capital of the United States
Middleburg is well known as horse country, and if you’re into that, you will love Salamander Middleburg, a luxury horse resort an hour from Washington D.C, with five-star spa amenities, an opulent interior with equestrian decor, outdoor activities like tennis and zipline, and of course, horse riding.
Watch dressage competitions and carriage-driving events at Morven Park International Equestrian Center in Leesburg and step into the hunting world at the Museum of Hounds & Hunting North America. Lastly, live out your English-landed gentry fantasies at several equine farms in Loudoun County that offer horseback riding lessons, summer camps, and competition training.
Be Artsy in the Arts and Culture District
Arts and mural seekers are not forgotten in Loudoun County. For example, Leesburg is an official Arts & Cultural District with murals, sculptures, and galleries, which are easy to find with a Loudoun Art Tours guide. Begin at the upcycled bicycles LoveWorks sign, then cross the road to Raflo Park with its abstract sculpture garden, see locomotive murals over an abandoned railway line, then take a photo of Leesburg’s famous “Discover Charm” teal mural.
Lastly, marvel at a historic mural of the “Journey to Freedom” on the facade of a Leesburg building. Lovettsville and Purcellville are also part of the LoveWorks trail with LOVE sculptures, and Ashburn has urban murals on the walls of its Alamo Drafthouse. In addition, there are music festivals, jazz concerts, and community theater productions across the county throughout the year.
Sip Wine in the Virginia Wine Countryside
Colloquially known as D.C. Wine Country, Loudoun County overflows with nearly fifty wineries on acres of rolling hills, overlooking valleys and vistas, with scenery straight out of your childhood fairytales. This is where a vehicle is essential for accessibility as the wineries are deep in the countryside; they make up for their quasi-isolation with activities, fall foliage in the right season, culinary treats, wine tours, and wine tastings. Surprisingly, Virginia winemaking goes back to the 1600s when Europeans planted vines for use as cash crops.
There are wines available for the most discerning oenophile to the clueless novice, and for either, there are countless winery options like Boxwood Estate Winery, family-owned Breaux Vineyards on over four hundred acres of land, or Casanel Vineyards, a smaller, family-run operation on eight acres growing grape varietals from different international locations. Research a vineyard of your choice to spend a day indulging in tours and tastings while relaxing in the serene countryside.
Every month, a wine event happens in Loudoun County, but the main one is in October for Virginia Wine Month. In addition, there is a plethora of distilleries, cideries, and craft breweries, such as the family-run Old Ox Brewery, Lost Rhino Brewing Co in Ashburn, and Wild Hare Cider, amongst many others. August is Virginia Craft Beer Month and is the perfect opportunity for a beer-hopping taste adventure.
Where to Stay In Loudoun County
Keeping with the old English vibes and countryside scenery, the most appropriate accommodation is cottage-style or village bed and breakfasts (not of the “air” kind). For example, Middleburg’s Red Fox Inn with cottages clustered around their main street, Dunthorpe Cottage on a farm with scenic vistas and a paddock for your horse, or Blue Hill Farm for rustic farm luxury; go countryside luxury with fine dining and decor at Goodstone Inn & Restaurant, Salamander Middleburg for uber-luxury horse resort, or a conventional stay at Lansdowne Resort & Spa with an expansive golf course, hiking and biking trails, and access to the Potomac River Trail for outdoor activities.