24 Hours in Middleburg

by Tracy Kaler  |  Published April 10, 2023

History meets culture in Middleburg, America’s horse and hunt capital. This charming small town, set among lavish estates and acres of farmland with more than 50 wineries nearby, is a jewel in the Northern Virginia countryside.

The leafy main street in Middleburg, Virginia. (Photo by Tracy Kaler for TravelMag)

Home to less than 800 people, Middleburg is a small town nuzzled at the foot of the Blue Ridge Mountains in Loudoun County, Virginia, about an hour’s drive from Washington D.C. Promising leafy streets, brick sidewalks, and quaint storefronts, the walkable, well-heeled enclave feels a lot like a European village, but with a sprinkling of Americana laced in.  

Middleburg has a deep-rooted history. Established in 1787 by Leven Powell, a Virginia statesman and Lieutenant Colonel in the American Revolutionary War, the town was the location of two battles in 1863 as part of the Gettysburg Campaign and a significant site in the Civil War. More than 160 buildings are listed on the National Register of Historic Places.

Jump ahead to the turn of the 20th century, and Middleburg was deemed the “Nation’s Horse and Hunt Capital,” eventually attracting public figures such as John F. Kennedy and Jacqueline Kennedy Onassis, Elizabeth Taylor, and Robert Duvall as residents. Nowadays, Middleburg oozes charm that melds with Virginia culture. It’s evident in the town’s historic district, fox hunting meets, steeplechase events, and equestrian lifestyle. Meanwhile, the region offers a spread of lavish estates, acres of vineyards, and dozens of wineries.

Have 24 hours in Middleburg? Here’s what to do, where to stay, and where to eat in this idyllic pocket of Virginia.

The Red Fox Inn in Middleburg dates to 1728. (Photo by Tracy Kaler for TravelMag)

Things to Do 

Less than one mile long, Middleburg’s historic district has been listed on the National Register of Historic Places since 1982. Much of the 19th-century architecture along Washington Street, the main drag, is well preserved, reflecting the days of yore. It’s home to high-end clothing boutiques, equestrian shops, art galleries, restaurants, and pubs. Spend a few hours browsing stores like Olde Millstones Vintage Thrift Shop (6 W Washington St) and Crème de la Crème (23 E Washington St) after lunch on the main street.

One of Virginia’s burgeoning wine regions, Loudoun County produces Chardonnay, Petit Manseng, Cabernet Franc, Tannat, and a growing list of varieties. More than 50 wineries lie within a 30-minute drive of downtown, with a handful occupying land in Middleburg, a short trip along John Mosby Highway. So, it’s nearly impossible not to stumble upon a vineyard or tasting room as you explore the area. 

A sprawling property showcasing gorgeous views makes Greenhill Vineyards (23595 Winery Ln) worth the stop, never mind the refreshing Viognier and heady Cab Franc, arguably one of the region’s best. Taste a selection of the winery’s offerings for $20. Down the road at 50 West (39060 John Mosby Hwy), winemaker Jason Burrus brings his California and Europe expertise – he previously made wine in Napa, Sonoma, the Central Valley, Malta and Moldova – to Loudoun County. 50 West produces Vidal Blanc, rosé of Sangiovese, and Chambourcin, among other wines, with tastings available for $22 to $25.

Greenhill Vineyards showcases gorgeous views. (Photo by Tracy Kaler for TravelMag)

Additional wineries a stone’s throw from downtown include Cana (38600 John Mosby Hwy), where winemaker Melanie Natoli puts her spin on Petit Verdot and Merlot, and Chrysalis Vineyards at the Ag District (39025 John Mosby Hwy), known for crafting wine from alternative varieties like Norton: a native grape that produces a dry, full-bodied red. Chrysalis has the most extensive planting of the heirloom fruit in the world.

A visit to Middleburg would only be complete with an equestrian outing. Watch the horses in action at the Middleburg Spring Races in Glenwood Park (Glenwood Park Ln), a circa 1911 Equestrian Center. The April event welcomes the season each year when daffodils and dogwood trees are in glorious bloom. The Virginia Fall Races are slated for the second Saturday in October at the same locale. And if you want to ride yourself, Salamander Resort & Spa’s Equestrian Center (500 N Pendleton St) offers 25 acres for guests and non-guests to participate in a guided trail ride, so saddle up.

Salamander Resort & Spa’s Equestrian Center offers trail rides. (Photo by Tracy Kaler for TravelMag)

Where to Stay

Capturing the essence of historic Middleburg, The Red Fox Inn (2 E Washington St), dates to 1728. The property features 22 individually decorated rooms, suites and cottages in five buildings scattered around the historic center. Perks range from in-room breakfast and house-made cookies to Egyptian cotton bedding and concierge services. If you prefer to stay in for dinner, the inn’s namesake tavern is on the ground floor.

For five-star luxury, look no further than Salamander Resort & Spa (500 N Pendleton St). This sprawling estate perched on 340 acres is about a 15-minute walk from the main street, yet it feels a world away from town. The stunning property captures the essence of Middleburg through its traditional, well-curated interior and upscale appointments alongside tons of atmosphere. Guests should expect hypoallergenic bedding, luxe terrycloth robes, and evening turndown service. Schedule a day of pampering at the on-site spa and relax by the wood-burning fireplaces in the cozy library or sophisticated living room. The hotel hosts several activities, such as hiking, biking, tennis, fitness classes, and more, so one could linger at Salamander for hours and have enough things to do. After a day of outdoor pursuits, sip a dirty martini or glass of Virginia wine at Gold Cup Wine Bar, located off the lobby.

Relax by the fire in the living room at Salamander Resort & Spa. (Photo by Tracy Kaler for TravelMag)

Where to Eat

On-site at Salamander Resort & Spa, Harrimans Virginia Piedmont Grill (500 N Pendleton St) is an acclaimed contemporary American restaurant highlighting local ingredients. Menu frontrunners include the Maple Leaf Farm duck, Long Stone Farms fried chicken with organic collards and buttermilk biscuit, and the shareable 30-ounce Tomahawk steak. Breakfast here is also a hit, providing an extensive selection for a morning meal. Choices range from smoothies and other healthy fare to the extraordinary Harrimans Breakfast (bacon or sausage and eggs with potatoes and toast) to a Chesapeake crab Benedict and buckwheat bananas foster bread pudding for a sweet tooth. Harrimans serves brunch on Sundays.

Enjoy a hearty breakfast at Harrimans Virginia Piedmont Grill. (Photo by Tracy Kaler for TravelMag)

Fresh ingredients from the Piedmont region transfer to the plate at The Tavern (2 E Washington St), the intimate low-ceiling space on the ground floor of The Red Fox Inn. Marked by scores of stone and dark wood, working fireplaces, and sporting art, the interior reflects the building’s Colonial roots. A four-course experience with optional wine pairings features a diverse lineup of dishes like shrimp and grits, burrata with roasted grapes, lamb Bolognese, and dark chocolate Basque cheesecake for dessert. Choose your dishes, then share family-style sides of crispy smashed potatoes topped with blue cheese and bacon and fried artichokes dressed in chimichurri aioli. Presenting a limited menu, the more casual Night Fox Pub on the second-floor plates Caesar salads, N.Y. strip steaks, and the restaurant’s addictive white truffle parmesan fries.

The interior of The Tavern at The Red Fox Inn reflects the building’s Colonial roots. (Photo by Tracy Kaler for TravelMag)

King Street Oyster Bar (1 E Washington St) offers what the name implies. Find the freshest bivalves from the East and West Coasts – out of the water no more than 24 and 48 hours, respectively – and a spree of seafood starters and main plates. Purists will likely stick with the raw oysters, best ordered by the dozen, and groups of two to four diners should indulge in the “Mermaid Tower,” an assortment of lobster, shrimp, raw oysters, and jumbo lump crab. Don’t miss the daily Happy Hour from 3:30 to 6 p.m, with $1 oysters and $7 small plates served alongside $7 cocktails and discounted beer and wine.

In the historic district, Salamander Resort’s Market Salamander (200 Washington St) is the place for coffee, a quick sandwich, bowl of soup, salad or double dip of homemade ice cream. Try the chef’s chicken and dumplings, the Maryland crab roll stuffed with crab salad and Old Bay mayo, or to nurse a hangover, the hearty Market Salamander poutine: a heaping pile of fries crowned with house gravy, cheese curds, and Virginia ham. The gourmet stop is also an excellent choice for breakfast (some dishes are served all day) before heading out to the wineries. Or opt for a snack, bottle of wine, the eatery’s house-pickled veggies, sauces, spreads, or made-from-scratch bread. Market Salamander offers indoor and outdoor seating, so depending on the weather, dine outside and watch the action on Washington Street, or grab a bite to go before you hit the road.

Grab a bite to go at Market Salamander. (Photo by Tracy Kaler for TravelMag)