This under-the-radar destination is rich in old world charm, including rolling hills, independent shops, small vineyards, and country inns.
These elements attracted icons like Jackie Kennedy and Elizabeth Taylor, who both called Middleburg home for a time.
You don’t have to be Jane Austen obsessed to be dreaming of the English countryside in 2025. This year is the 250th anniversary of the Pride and Prejudice author’s birth and the idea of an idyllic, rose-scented, never-too-hot English countryside has permeated imaginations, bucket lists, and social media feeds seemingly the world over. While we cannot all swing a trip to Austen’s birth country this summer, we can visit somewhere a little closer to home—especially if your home is on the East Coast.
Middleburg, Virginia, about an hour from Washington, D.C., is the state-side answer to a Cotswold’s craving, and there has never been a better time to go.
Known for its sprawling horse farms, rolling vineyards, historic country inns, and independently owned boutiques, Middleburg has the type of streets and scenery that seem directly pulled from one of Austen’s books. Yet the town has managed to fly under the radar for years, despite being located in the wealthiest county in America (Loudoun County) and despite being a favorite destination of numerous political and Hollywood icons.
Elizabeth Taylor called Middleburg home during her marriage to Senator John Warner, and the Kennedys owned a 166-acre farm here, which they used as a weekend home during their time in the White House. And although JFK famously disliked his weekends here, Jackie remained a local fixture in town even after her husband’s assassination and was a regular at The Red Fox Inn and Tavern.
“The unassuming lifestyle of the Virginia Piedmont,” is what charmed Jackie, says Matilda Reuter Engle, who runs Red Fox and whose family has been in Middleburg for seven generations. That lifestyle—with its tony pursuits of fox hunting, horse racing, and polo playing—adds to what Engle points out is Middleburg’s “old-world charm.”
The old-world, Austen-esque charm is palpable in the postcard-sized downtown, with antique stores and independently owned boutiques like Crème de la Crème, which sells a highly curated selection of European homewares. Owners Tara and Ben Wegdam opened the shop 25 years ago, after successfully running a similar business in Holland. Middleburg proved to be a natural place to open their business after they left Europe. Tara Wegdam is quick to point out that it’s Middleburg’s “European charm meets everyday living” that has made the shop such a success. They currently have a customer membership base of more than 100,000 people and run several other locations of their shop in Virginia and Maryland, although the Middleburg spot remains the biggest travel-worthy draw.
Many shops have followed in Crème de la Crème’s footsteps and have thrived in the town, whose population is just 700. Middleburg Books, which opened in 2023 by a local librarian, credits much of its success with those who travel here. “We’ve found that about 75 percent of our customers are out-of-towners,” says owner Mary Beth Morell. “It’s been a delight to see our charming little jewel-box of a bookshop become something of a destination in its own right.”
Other small shops, such as Highcliffe Clothiers, which sells elegant country wear, Federal and Black, which offers home goods and gifts, and Knead, which bakes homemade pizzas, Virginia peanut cookies, and sells sommelier-selected wines, all have devoted fan bases.
Middleburg’s wineries have also helped to establish the area as a destination. And while the wine produced here may not be truly old world, it is a thing of beauty on its own. Virginia’s wine industry has grown substantially in recent years, and local producers, including Greenhill, Boxwood, and Cana are the perfect spots to take it all in.
Outside of town, visitors will find two country inns: Salamander and Goodstone. Both hotels are tucked away from town and on substantial parcels of land, and it’s easy to imagine any Jane Austen heroine wandering their grounds.
