Spending time in Middleburg, Virginia, located in scenic Loudon County, feels like soaking up the sunshine and vino in a European wine village. This quaint town boasts the same timeless charm as a destination in the French Countryside—but with its own authentic sense of Virginia soul. From wine tasting to fine dining and a lineup of fun spots to shop and play, here’s why a trip to Middleburg can feel like a trip abroad, without the stress of international travel.
Visiting this region’s famed vineyards and wineries is essential
Whether or not you’re a wine person, spending time at one of Middleburg’s beautiful wineries is a must-do while in town. This area boasts more than 20 wineries within 30 minutes of the historic hamlet. There are multiple spots to sip and savor, ranging from scenic vineyards to delightfully decorated tasting rooms.
Check out Boxwood Winery, which is the estate winery of John Kent Cooke, who owned the LA Lakers and Washington Redskins. This spot is famous for Bordeaux blends. It features a circular underground cave room lined with French wine barrels, which doubles as a tasting room, making for a dreamy sort of ambiance.
At Greenhill Vineyards, don’t miss the Blanc des Blancs sparkling, which is so acclaimed it actually made it into the gift bags at the 2016 Academy Awards. This destination boasts a cathedral-like Barrel Room, which doubles as a regal venue for private dinners and events.
At Chrysalis Vineyards, encounter the largest planting of Norton grapes in the world. The property also has a herd of cows and a dairy to make cheeses, plus a bakery that uses grain from the farm for fresh breads.
Stop into Cana Vineyards to celebrate “woman power,” as the property’s winemaker Melania Natoli won the Virginia Governor’s Cup in 2023 (the first woman to do so!).
BONUS: If you’re not into wine, that’s OK, too! Visit Lost Barrel Brewing—an upscale craft brewery on a former horse farm that has the design aesthetic of an estate winery (so it feels as if you’re on a wine tasting excursion, anyway!). This spot isn’t just pretty—it contributes to the community, too. They made a beer for a Mississippi charity last year with Washington Nationals baseball legend Ryan Zimmerman, who is a known friend of the owners.
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You’ll never go hungry with these delectable dining establishments
Grab a morning pick-me-up at Common Grounds or Cuppa Giddy Up, two cute local coffee shops serving up the caffeine and good vibes needed to kickstart a day of adventures. Visit Tremolo, a local gem of a restaurant for food from a James Beard-nominated chef and wine by a master sommelier. For seafood, try King Street Oyster Bar, which brings the ambiance and flavors, as it’s set in a former bank building for a fun and historic setting to enjoy a meal.
Activities Outside of Wine
Admittedly, wine is king (and queen) in this region, but there are plenty of things to do outside of imbibing. This destination is unparalleled for its living history, including 160 buildings listed on the National Register of Historic Places. Go for a stroll along Washington Street, and admire the architecture and its lineup of fashionable independent stores that offer everything from cocktail gowns to equestrian wear. There’s also the National Sporting Library & Museum, which is an incredible library, museum, and gallery. It’s known as the nation’s leading resource on field sports and equestrian pursuits.
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Rest up for another day of wine and wonder at these cozy accommodations
Red Fox Inn & Tavern is the oldest building in town, and was established by a cousin of George Washington. This spot claims to be the longest still-operating inn in the country. Since Jackie Kennedy and Liz Taylor were known to be frequent guests, you’ll be resting your head in a place fit for celebrities.
At Salamander Middleburg, bask in the glory of the offerings of a five-resort that is ushering in a sense of European refinement to the Virginia countryside. Explore the property’s equestrian trails, indulge in fine dining and a top-tier wine list, and know you’re staying in the best of the best—a business owned by the entrepreneur Sheila Johnson. There’s also the 18-suite inn, Goodstone Inn & Restaurant, which is set on 265 acres of rolling countryside, renowned for its unmatchable amenities including a heated outdoor pool, farm walks, wine cellar, and farm-to-fork fine dining.
And just outside town, encounter Welbourne Inn, a rustic, late 18th-century manor house B&B and horse farm that’s currently owned by descendants of Col. Richard H. Dulany (founder of the Upperville Colt & Horse Show). The house boasts five upper-floor rooms and a large ground-floor room. There’s an opulently furnished lounge featuring an impressive collection of antiques and oil paintings depicting hunt country scenes that seemingly transport you to another land. Spending time on the scenic front porch in the evening with a bourbon cocktail in hand is known to be a popular pastime for guests and the inn’s friendly hosts.
Middleburg Doesn’t Disappoint in its European Feeling Ambiance
Those who enjoy the wine tasting scene in Middleburg should look into exploring these other Virginia wine country outposts—5 Stunning Virginia Vineyards With Tastings For $20 or Less. While you’re in the area, be sure to take a side trip to this Charming Small Town In Virginia That’s Perfect For A Fall Day Trip, Leesburg, which can serve as a charming fall getaway with historic sites, nature trails, and local dining. Virginia is full of hidden gems to uncover, and there’s no need for a passport for those who seek an international-feeling experience in the Old Dominion State.
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