7 Virginia and Charlottesville Wineries You Have to Visit

This post contains affiliate links. You do not pay additional by making a purchase through an affiliate link, which helps to support this blog’s livelihood. 

Bluemont is one of my favorite Virginia and Charlottesville wineries
A Bluemont Vineyards pairing event

If you’re visiting Virginia, you may want to add Virginia and Charlottesville wineries to your list.

These days Leesburg, Middleburg, and Purcellville are part of Northern Virginia, but growing up they were part of the country. …not anymore! Loudoun County has grown into its own as a major hub close to Dulles Airport that is very close to home (and you can read about my Dulles humble beginnings).

Northern Virginia west is not just where you get your apple pies for Thanksgiving or where you visit one of several known local spas like Lansdowne.

AND, it’s also in the heart of Virginia’s wine country. The winery trail is one attraction that gets locals and travelers to visit.

And these are my 7 insider picks of Virginia and Charlottesville wineries you want to check out especially if you only can choose a few:

But first a few good recommendations and tips. In most cases, bring a picnic. Yes, bring your own food!… brie and French bread and assorted cheeses and grapes to go with more crushed grapes (wine).

Do the tastings. They are probably the most fun as you try with your friends and see their preferences. And rank the ones they like in a wine game board. Plus, you get a free logo wine glass to commemorate your visit.

Outside dogs are acceptable, and babies inside too. But, you won’t see many as most find a sitter. Other than that, go on a nice weather day to enjoy the scenic views. And if it’s not so nice out, there are several below that are better indoor anyway because of the large barn structure, and I point those out below. 👇

Barrel Oak – see the picturesque rolling wine hills.

rolling hills of virginia and charlottesville wineries

Bluemont – up the hill (951 feet up from sea level) and a hike off the beaten path in Bluemont, VA, but totally worth the map scavenger hunt drive! 🗺️

They have quaint amazing girly events like the Girl Scout Cookie 🍪 wine pairing and other thoughtful pairings throughout the year, like chocolate & wine… or tapas wine pairings where you don’t have to wait until Valentine’s Day or take a trip to Spain to enjoy. You can even do grape stomping for a photo opp! But please no sipping wine from those crushed grapes 😃

Breaux – be in awe of expansive scenic views that do take your breath away. Surrounded by 3 acres of grapes, you want to enjoy a spot outdoors, so bring a blanket or event chairs. This one can get crowded in Purcellville which many Northern Virginians have moved out to, but worth it if you like being around the social hoopla.

Chrysalis – when in Middleburg, visit this cute town that you can miss if you blink and has now all grown up. Chrysalis Vineyards is known for Sarah’s Patio Red edition sold in most large grocery store wine selections, plus their 100% Norton grape wines served in Chrysalis’ AG District Tasting Room and backyard patio pergola. The drive is relaxing and takes you away from the hustle and bustle of NoVa.

Sunset Hills – is a Purcellville red barn winery experience great for an indoor or rainy day event. My club member friends say this one is the “most consistent” wineries with 13 grape varieties on 75 acres… and I love all on this list for different reasons, so I’ll go along with that.

Stone Tower – get there early so you can have a table indoors, and another great one for gray days. It’s located in Leesburg so you’re in the heart of Virginia wine country. They have events like a Lobster Boil. 🦞 They even serve pizza on the menu. Who says wine and pizza don’t pair? Red or white… your choice.

And for the super best-tasting wines in Virginia… go out further west toward Charlottesville (known for the University of Virginia and where Thomas Jefferson has roots).

These are my two faves 💕:

Barboursvillefall is a beautiful time of year to go out toward Barboursville. Just when the air is starting to cool and getting crisp, every nice weather, work free-day is a good opportunity to check this winery out.

Barboursville ranks high in Virginia wines (and I would agree!). It’s attached to its Italian restaurant and an inn that you can learn about its history.

virginia and charlottesville wineries like Barboursville with the ruins
Barboursville ruins designed by Thomas Jefferson

And drumroll… I’ve saved the best for last. It’s a hidden gem and Dave Matthews (yes! from the band) winery named Blenheim. It’s a boutique vineyard. Especially if you like fruit-forward and quality wines, this is the cozy white barn you want to visit. And you can easily miss it…

Except you’re across the street from the Trump Winery estate (that I’ve never been into), but you know where you’re located when you see this place that stands out and then you can check out the smaller, boutique venues.

And as you take more country drives with country signs, you’re surrounded by remote boutique Charlottesville wineries you can stop in.

And as you get closer to C’ville, you have Virginia mountain views. ⛰️ It’s “purple mountains majesty” and a beautiful drive as you get closer to Thomas Jefferson’s Monticello land. And then you’ve completed your tour of Virginia and Charlottesville wineries.

2 thoughts on “7 Virginia and Charlottesville Wineries You Have to Visit”

Leave a Comment