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The Four Best Wineries To Visit in Middleburg, VA

Middleburg, VA

The Loudoun Wine Trail abounds in picturesque boutique wineries, scenic vineyard views, and a relaxing atmosphere perfect for a weekend getaway. If you’re unsure where to start exploring, we recommend four fabulous wineries in Middleburg, VA. Enjoy unforgettable wine tours in Middleburg with our luxury vehicles.

1. Greenhill Vineyards

Middleburg, VA, is the ideal location to make your escape from bustling cities and busy roads. This becomes obvious as soon as you glimpse Greenhill Vineyards, located only minutes outside the town.

This boutique winery produces award-winning wines from local grapes. It cultivates many grape varieties, from the classic Chardonnay and Riesling to various experimental vines, and is one of the oldest and most picturesque vineyards in Northern Virginia.

Greenhill Vineyards boasts sumptuous French, Italian, and Spanish mezze menus to accompany your wine of choice. You can choose seats in the Tasting Room, on the terrace, or out on the lawn.

2. Chrysalis Vineyards

You’ll find Chrysalis Vineyards only about eight minutes east of Greenhill Vineyards. This winery grows some Spanish grape varieties, but its great passion is the Norton, an indigenous grape ideally suited to the Virginia terroir. Chrysalis currently makes six styles of wine from this grape variety, ranging from sweet and light to robust and bold.

Chrysalis also offers a varied menu of appetizers, pizzas, salads, and other tasty bites that pair well with wine. Some of its products, like cheeses and sauces, come straight from its farmstead. The winery features a large tasting room and an outdoor area with a breathtaking view of the Bull Run Mountains.

3. Boxwood Estate Winery

Boxwood Estate Winery sprawls over 26 acres of sustainably grown traditional Bordeaux grapes like Cabernet Sauvignon and Merlot. The winery, a passion project of former Washington Football Team president John Kent Cooke, specializes in French-certified red wines. It’s located on the historic Boxwood Farm, a few minutes south of Middleburg.

Boxwood Estate Winery offers several wine-tasting packages and a light menu that enhances luxury wine experiences. Its gorgeous surrounding views, sophisticated seating, and, of course, high-quality grapes place it firmly among the best wineries in Middleburg, VA.

4. 50 West Vineyards

Another well-loved local winery near Middleburg, 50 West Vineyards serves wines from grape varieties like Albarino, Sauvignon Blanc, and Cabernet Sauvignon. The winery has a beautiful rustic-looking tasting room and a private event venue.

50 West Vineyards lets you choose between a guided tasting menu and freestyle food and wine menus. They serve cheeses, spreads, crackers, and other tasty treats that all go well with a glass of wine.

Book Your Luxury Wine Tour With Chariots for Hire

Exploring wineries in Middleburg, VA, is the perfect choice for a fun excursion with friends or your significant other. Enjoy wine-tasting tours year-round or feel the harvest season magic with the best autumn winery tours in VA.

Hiring one of our fancy limos or high-end buses for your winery trip ensures a deluxe, worry-free experience. Book your tour today.