Experience The Best Of Small Town America At An Under-The-Radar Wine Region In Virginia

Acres and acres of grape vines growing among the rolling green hills around Middleburg, Virginia, will have you thinking of the Tuscan countryside. In reality, this pastoral paradise is located just over one hour outside of the bustling U.S. capital. 

Middleburg has the best of what small-town America has to offer: a historical downtown, locally owned shops, a picturesque inn, and restaurants so good they draw foodies all the way from Washington, D.C. That's why the community — with a population well below 1,000 — has landed on lists by Frommer's, Southern Living, and AARP ranking the country's prettiest or most charming small towns.

Five wineries and vineyards surround Middleburg, making the hamlet a compelling option for wine lovers looking to spend a weekend exploring the countryside and visiting tasting rooms. Winemaking in Virginia began in the 1600s after some of the first colonists arrived from England, and the practice experienced a resurgence in the state in the 1960s. Virginia has recently received more recognition as an appealing destination for a scenic wine vacation. Its central region, which offers the road trip of a lifetime for wine lovers, is the most celebrated for its vintages. Meanwhile, Middleburg, in northern Virginia, remains an underrated spot for oenophiles. 

Middleburg is a destination where the lodgings are as significant a part of the experience as the activities you do or vistas you enjoy. Though a tiny town, it's home to first-rate options for overnight stays, including the excellent Salamander Resort and the boutique Red Fox Inn. The luxurious Goodstone Inn is located a few miles north of town. All of these options offer in-house restaurants and other amenities, and they'll set you back more than $400 per night. More budget-friendly options are available further east on Highway 50 in the suburbs of Washington, D.C.

Dozens of shops and art galleries are squeezed onto Washington Street in Middleburg's historic district, which is less than a mile long. There are also a wide variety of restaurants for every palate. Hunter's Head Tavern serves farm-to-table dishes from a colonial-style house. Tremolo is a highly rated tapas bar that one diner described on TripAdvisor as a "real foodie find." And if you're interested in sampling mid-Atlantic oysters, King Street Oyster Bar offers them grilled or on the half shell.

The beauty of the area might put you in the mood for an outdoor adventure. If that's the case, head to one of three parks surrounding Middleburg: Sky Meadows State Park, Shenandoah National Park, and Great Falls Park, one of Virginia's most underrated parks that's full of waterfalls and scenic hikes. If you want to stay in town and get a feel for the local history, you can find it all around Middleburg. Over 160 of its buildings are on the National Register of Historic Places. For a more in-depth look, the National Sporting Library and Museum in the middle of town explains Middleburg's past and its designation as the nation's "Horse and Hunt Capital."

You can also get a taste of local history at some of the nearby vineyards — in addition to the wine, that is. Boxwood Estate, now the setting of an award-winning winery, was founded in the 1700s as one of the earliest horse farms in Middleburg. Later, it was home to Brigadier General Willy Mitchell, who played a large role in the creation of the U.S. Air Force. The winery is a National Historic Landmark that celebrates its past while adopting modern viticulture practices. Tastings and pairings range from $35 to $75 per person.

Another historic farm is now home to Greenhill Vineyards, two miles east of Middleburg. The land was established as a working farm in 1762, and in the 1980s, it shifted to growing grapes. The vineyard offers $20 tastings. Outside its tasting room is a large, grassy expanse dotted with tables for visitors to enjoy the outdoors.

Cana Vineyards offers views of the Blue Ridge Mountains and the surrounding farms from a second-story deck outside its tasting room. The hillside winery won the Virginia Governor's Cup in 2022 — a competition hosted by the Virginia Wineries Association. Cana's top winemaker became the first woman to ever receive the award. Also nearby is 50 West Vineyards, with its large, modern tasting room perched on a bluff, and Slater Run Vineyards, which has a long family history and a French-style influence. If you want the ease of visiting multiple vineyards around Middleburg without the hassle of driving or navigating, multiple local tour companies offer driving services and work with visitors to map out their visits.