Plan Your Virginia Autumn Wine Weekend Now

Did you know the Old Dominion is home to over 300 wineries? While it seems like a daunting task to feature every one, we wanted to start with a fall wine guide featuring wineries in Middleburg, Leesburg and Charlottesville, VA. Start planning your autumn wine weekend now!  


50 West Vineyards 

39060 John Mosby Highway  

Middleburg, VA 20117   

High upon a bluff in Middleburg sits the picturesque 50 West Vineyards. Sipping wine here is easy, with its gorgeous views of the Bull Run Mountain Range. Dress warmly when you visit, as 50 West Vineyards sits atop a hill (the views are spectacular!) If you decide you want to become part of the 50 West family, they offer a club for returning members.   

Chrysalis Vineyards at the Ag District 

39025 John Mosby Highway (US 50)  

Middleburg, VA 20117 

We love Chrysalis’ Albariño white wine, which is not very common in the U.S. It’s dry and crisp with plenty of citrusy flavor. We adore their menu too, as it’s full of perfect options to pair with Chrysalis’ wines. The mini calzones are a great deal at three for $15, with choices like spinach, artichoke hearts and alfredo, pepperoni, sausage, salami and marinara and more. Like 50 West Vineyards, Chrysalis offers a VIP club with perks like free tastings for up to four people any time you visit, complimentary tastings for six and free cake on your birthday.  

Cana Vineyards and Winery of Middleburg 

38600 John Mosby Highway  

Middleburg, VA 20117 

Cana Vineyards and Winery is the perfect escape from busy city life. The venue sits on 43 acres of farmland in the Virginia countryside. It’s simply heaven to take in in a gorgeous sunset at Cana while sipping on a Cana Merlot. Best of all, Cana is both family and pet-friendly. Dedicated adults-only spaces and dogs on a leash are allowed in public areas on the ground level, in the Sunset Pavilion and the grounds of the vineyard.  

Greenhill Winery & Vineyards 

23595 Winery Lane  

Middleburg, VA 20117  

This adults-only (21+) winery and vineyards is a great place for a cozy fall picnic. Their charcuterie boards are incredible and well worth snagging for an afternoon at Greenhill. The 120+ acre property has lots of historical flair too, as a Club House on the property harkens to 1762. Don’t miss the Little River that runs along the southeast property line, along with a natural pond for some perfect photo ops.   

Boxwood Winery 

2042 Burrland Rd.  

Middleburg, VA 20118 

Boxwood is the dream of Jack Kent Cooke, colorful former owner and president of the Washington Football Team. He was an admirer and collector of French wines (especially Bordeaux). Boxwood specializes in premium red and white wines in the Bordeaux tradition. The winery is located in an area with lots of Revolutionary War and Civil War history.   



Fabbioli Cellars 

15669 Limestone School Rd. 

Leesburg, VA 

Fabbioli Cellars’ owners Doug Fabbioli and Colleen Berg first started thinking about starting a winery over 30 years ago. They moved to California in the ‘80s and wanted to find a piece of land to grow grapes. They ended up moving back East 10 years later and one day, Colleen was driving around with their young son and they stumbled on a 25-acre piece of land just north of Leesburg in Loudoun County. Let’s just say, the rest is history!  

The Vineyards and Winery at Lost Creek 

43285 Spinks Ferry Rd.  

Leesburg, VA 20176 

Like Doug Fabbioli and Colleen Berg, Amy and Todd Henkle had a dream to open a winery after honeymooning in Bordeaux, France. The two created The Vineyards and Winery at Lost Creek about 10 years ago and the elegance of their wines shows. We love that they have a Sunday brunch menu with wine pairings — perfect for a weekend out with friends.  

Stone Tower Winery 

19925 Hogback Mountain Rd.  

Leesburg, VA 20175 

The sweeping views are part of what makes this multi-generation-owned family winery beautiful. You can’t help but feel instantly at home with the Huber family taking care of you. Their Harvest Barn menu is ideally suited for fall comfort foods and post-wine tastings. There’s chili, smoked gouda mac and cheese and more.  

Willowcroft Farm Vineyards 

38906 Mt. Gilead Rd.  

Leesburg, VA 20175 

Willowcroft Farm Vineyards is located high atop the Catoctin Ridge with breathtaking views of Loudoun Valley and the Blue Ridge Mountains. The peaceful oasis has been around nearly 40 years. Notable wines include their 2017 Cabernet Sauvignon and a 2018 Riesling Muscat-Ottonel, splendid for your upcoming Thanksgiving dinner.  


Knight’s Gambit Vineyard 

218 Knole Farm Lane 

Charlottesville, VA 22901 

Knight’s Gambit is a truly family-owned winery, dating back to a purchase made in the 1970s. In 2003 the owners planted over five acres, producing an amazing pinot grigio, rosé, chardonnay and more. On a bright fall day, it’s hard to ask for more than enjoying a relaxing glass of wine on the vineyard’s deck. 

Thatch Winery 

1650 Harris Creek Rd. 

Charlottesville, VA 22902 

Thatch has truly embraced pandemic times by specializing in wine flights. The flights are able to be enjoyed at the safety of a table without moving around. Four half-glasses are curated by Thatch’s wine team. If you’re a sweet wine lover or a crisp wine lover, personalized tastings are offered just for you. Don’t forget to add in some picnic snacks like cheese and charcuterie too!  

Blenheim Vineyards 

31 Blenheim Farm  

Charlottesville, VA 22902 

Blenheim Vineyards is open outdoors from 11 a.m. until 5:30 p.m. on Thursdays through Sundays. There are flights, glasses and bottles of wine for sale and just FYI: groups of eight to 16 can visit the vineyards by reservation only. Beginning Nov. 4, the venue closes at 4 p.m. 

Meriwether Springs Vineyard & Brewery 

1040 Owensville Rd. 

Charlottesville, VA 22901 

Enjoy a combo vineyard/brewery with lots to do, including a live music series that runs through the end of November. Don’t miss the wood-fired pizzas prepped in their “big green pizza bus,” made-to-order and hand tossed. Paired with a uniquely Virginian 2018 Petit Verdot, it’s simply heaven.  




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