This Virginia Town Has The Biggest Heart

Located mid-way along an old trading route, pretty Middleburg has made a name for itself as one of the most (if not the most) friendly towns in the South. Although formally established in 1787 by Lieutenant Colonel Leven Powell, a Revolutionary War veteran who bought the land from a relative of George Washington, the location was already well-known as a stop for stagecoaches traveling between Alexandria and Winchester.

Previously known as Chinn's Crossroads, Powell renamed it "Middleburg" after its location halfway between these two well-established Virginia towns. It’s still a handy location for modern-day travelers thanks to its proximity to Washington, D.C., 50 miles to the east, and Dulles International Airport, just 20 miles away.

And that heartfelt, welcoming spirit? Well, it lives on, with Middleburg’s early years as a hospitality hub still very much evident nearly 250 years later.

Historic Hospitality Since 1728

The earliest evidence of Middleburg’s famous hospitality can be seen at The Red Fox Inn & Tavern. Opened in 1728 by Joseph Chinn as Chinn's Ordinary and claiming the title of the oldest continually operated inn in the United States, this attractive stone building has certainly seen its fair share of history.

It was here that Confederate Colonel John Mosby and his Rangers reportedly gathered during the Civil War, and by the 1920s, Middleburg had assumed a new identity as both a social and an equestrian center, earning the title of “The Nation's Horse and Hunt Capital.” This reputation got an even bigger boost in the early 1960s when President John F. Kennedy and his wife started visiting regularly, and Jackie Kennedy soon became a fixture riding with the Orange County Hunt.

However, the town’s horse and hound tradition goes back even further than the Kennedys. The country’s first-ever fox hunt took place nearby in 1840 with the Piedmont Fox Hounds, while the Masters of Foxhounds Association of North America was set up here in 1907 to protect and preserve the nation’s foxhunting traditions. Add to this the fact that the area hosts several MFHA-recognized hunt clubs, multiple polo teams, and some of the country's most prestigious thoroughbred breeding farms, and Middleburg is quite literally the beating heart of Virginia’s equestrian world.

Other Equestrian Traditions in Middleburg

But Middleburg’s connection to horses doesn’t end there. Glenwood Park, founded in 1911 for the Middleburg Spring Races, is recognized as Virginia's oldest steeplechase. An April event originally hosted by the Middleburg Hunt to entertain farmers whose land they’d used for the foxhunting season, it now draws crowds from across the country.

Since then, the racing schedule has expanded, with the Virginia Fall Races taking place in October. Both it and the spring races attract upwards of 10,000 spectators, with clear views of the entire steeplechase course from any vantage point thanks to the park’s amphitheater-like terrain.

Another must-visit for horse lovers is the National Sporting Library and Museum. Set in a Federal-style mansion dating from the 1800s, the museum and research center preserves horse and field sports history through its vast collection of more than 20,000 books dating all the way back to the 16th century. Be sure to pose for a selfie in front of the establishment’s signature horse statue outside the entrance.

Other Year-Round Festivals and Events

You’ll also experience Middleburg’s big heart when you visit other community events and festivals. One of the best is the four-day Middleburg Film Festival, which takes place in October and attracts around 5,000 movie fans to screenings at the posh Salamander Resort, the historic Middleburg Community Center, and the National Sporting Library and Museum.

Other annual events include Art in the Burg in May, an arts and craft-driven outdoor festival; the family-friendly National Night Out in August; and June’s Upperville Horse Show, the oldest such event in America, which is hosted in neighboring Upperville.

You can also sample the town’s huge heart during Middleburg Day, a community-wide celebration held in October that’s as much fun for visitors as it is for locals, with its food, games, and music. Independence Day is another great chance to participate, with celebrations taking place at the Middleburg Community Charter School on July 4. There are also fun Winter and Summer Sidewalk Sales during the Presidents Day weekend and the first weekend in August, respectively.

The Bottom Line

Pay a visit to Middleburg, and it’ll soon become abundantly clear that this charming old small town has a heart…and a big heart, at that. From its modest start as a stop for stagecoaches to its becoming Virginia’s top equestrian destination, this community of fewer than 700 souls has never lost sight of its roots as a place of hospitality. With a community center that has welcomed millions of visitors since it opened in 1948 and events like steeplechases and fox hunting, there’s a genuine small-town, big-heart community feel to Virginia’s most charming community.