12 Best Wineries near Upperville

Slater Run Vineyards Winery • $$
1500 Crenshaw Rd, Upperville

“A nice laid back place to wind down after a great weekend …“

4.7 Superb21 Reviews
Naked Mountain Winery Wineries • $$
2747 Leeds Manor Rd, Markham - 7.5 miles

“Children welcomed INSIDE and cherished here!! We loved this winery! There were 8 adults and our 3 month old grandson. We were welcomed and felt at home. The wine is delicious and the food was yummy! They made us feel like family. We even hung out with Beans the cat. Thanks for a fun relaxing afternoon.“

4.9 Superb50 Reviews
Otium Cellars Winery • $$
18050 Tranquility Rd, Purcellville - 11.3 miles

“Gorgeous views, great wines.“

4.8 Superb39 Reviews
Arterra Wines Winery • $$
1808 Leeds Manor Rd, Delaplane - 4.9 miles

“We had a great time visiting. Really high-quality and slightly unconventional wines. Very friendly people and a beautiful property. Folks who are really into the mainstream of Virginia wines should do themselves a favor and take a very rewarding step off the beaten path with Arterra.“

4.8 Superb35 Reviews
Boxwood Estate Winery Wineries • $$
2042 Burrland Ln, Middleburg - 7.87 miles

“Great wine, great people, beautiful location.“

4.5 Superb108 Reviews
Three Fox Vineyards & Farm Brewery Wineries • $$
10100 Three Fox Ln, Delaplane - 5.71 miles

“We so enjoyed our afternoon here! I love the many options for seating and that you can bring your dogs most places. I also absolutely loved that you could order glasses or flights from the bar and take them anywhere on property. Appreciated all the room to spread out and enjoy the scenery. Wines were good with a few uncommon but delicious options too. We will definitely be back here in the fall when we’re in the area. Pizza is honestly just ok, so I’d recommend bringing your own snacks.“

4.5 Superb100 Reviews
Delaplane Cellars Wineries • $$
2187 Winchester Rd, Delaplane - 3.99 miles

“Sunday, April 22, 2024, my wife and I were entertained at Delaplane Cellars tasting room by our old friends Keith & Viqui Dill AKA the Dill Pickers. We had a fantastic time listening to some great Bluegrass and Blues selections while enjoying several glasses of exquisite wine. We are hoping that they will book the Dill Pickers in the future and give us more than one day's notice so we can invite several friends to their venue. The staff were very courteous and attentive to our needs. As a disabled Vietnam veteran, I sometimes am not the most graceful so when I accidentally knocked over my glass of wine the staff were there instantly to clean up the mess and replace my wine. Our visit was exhilarating and the views were beautiful.“

4.5 Superb92 Reviews
Barrel Oak Winery and Brewery Wineries • $$
3623 Grove Ln, Delaplane - 7.66 miles

“Four of us did a wine tasting and had 2 pizzas and their tostadas. We loved their special to get 1 pizza and 2 glasses of wine. We each brought a bottle to take home and share; we really enjoyed both their food and wine. Next time we will try their beer side. They had plenty of space (we enjoyed the loft) and the views were good.“

4.4 Superb108 Reviews
Veramar Vineyard Wineries • $$
905 Quarry Rd, Berryville - 8.77 miles

“Relaxing place to go for a glass, bottle or tasting. The view is a bonus“

4.6 Superb26 Reviews
Twin Oaks Tavern Winery Wineries •
18035 Raven Rocks Rd, Bluemont - 9.12 miles

“First time visiting in a few years and even better than we remembered. Wonderfully decorated and comfortable tasting room to enjoy the views and live music. The Make Me Blush sangria is one of the best sangrias I’ve had…definitely recommend getting it and trying all in the sangria flight. Took home a bottle of Chardonnay after also enjoying a white flight.

Already looking forward to our next visit!!“

4.7 Superb16 Reviews
Bogati Winery Wine Bar • $$
35246 Harry Byrd Hwy #190, Round Hill - 10.72 miles

“Loved the wines!! The ambiance was amazing!! Don’t let the outside fool you!! Beautiful inside ❤️“

4 Good4 Reviews
Chateau O'Brien At North Point Wineries • $$$
3238 Railstop Rd, Markham - 8.57 miles

“We visited three wineries during our tour, and this one stood out by far for the exceptional quality of its wine. The experience was made even more special by the time we spent with the owner—warm, knowledgeable, and passionate. A truly memorable tasting, and we couldn’t leave without taking a few bottles home to enjoy!“

3.1 Average30 Reviews

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