6 Best Wineries near Middleburg

Red Vineyard Winery • $$
8 E Washington St, Middleburg

“My wife and I come here multiple times a year and each time we are blown away by the quality of service and the culinary experience. James has been our server many times and treats all guests like family. His knowledge of the menu as well as the history of the restaurant enhances the fine dining experience. I highly recommend making a reservation for the 4 course tasting menu with the wine pairing.“

4.6 Superb74 Reviews
Cana Vineyards and Winery of Middleburg Wineries • $$
38600 Little River Tpke, Middleburg

“A relaxing location close enough for a short trip, but still has views of the rolling hills of Virginia. The owners, staff, and winemaker are informative and if you stop in around the right time, you may get an invite to help pick grapes or bottle wine enabling you to learn more about the process. This was one of the few wineries we've ever visited that both me and my wife enjoyed all of the wines. Children and dogs are allowed, though with some limits (dogs can't come inside due to new Virginia regulations and children are asked to stay on the ground floor). All in all, Cana Vineyards and Winery is a great place to get relax for a few hours when you get a chance, and then head down to Middleburg for dinner and shopping!“

4.6 Superb48 Reviews
Boxwood Estate Winery Wineries • $$
2042 Burrland Ln, Middleburg

“Recently visited with a party of 7 while on a girl's trip to a nearby spa. The service was great. Marcus was our waiter & he was awesome!. We all enjoyed the cheese & wine pairing. I'd definitely revisit and go to the caves“

4.3 Superb63 Reviews
50 West Vineyards Wineries •
39060 Little River Tpke, Middleburg

“Beautiful views, good wine, new facilities are very nice with plenty of outdoor and indoor seating. Wish they had things to eat other than cheese and cheese spreads and crackers/bread since they do not allow outside food, but a great place to enjoy wine and the scenery“

4.3 Superb54 Reviews
Greenhill Vineyards Wineries • $$
23595 Winery Ln, Middleburg

“It is a nice winery, with large outdoor spaces with tables and benches, great for a picnic. The site is very clean and well organized. Wine is excellent, but some wines are available only by bottle, not by glass. Unfortunately, you can't get "wine tasting" outside (you can only get a glass or a bottle). Place is elegant, but the bill is a bit more expensive than other wineries.“

3.8 Good73 Reviews
Chrysalis Vineyards at The Ag District Winery • $$
39025 Little River Tpke, Middleburg

“We were in Middleburg, and a friend recommended this winery. Of all the wineries we tried in the Middleburg area, this one was our favorite. The 2021 Norton and Albarino white were to die for. The Petit Verdot was also amazing.We saw a lot of negative reviews about the food. But we decided to try it anyway. We got the Thai pork belly, and the pesto panini. We can’t speak to the pizza, but what we ordered was really good. Highly recommend this winery. The food is good, the wine is good. The views are spectacular. What more could you ask for?“

3.6 Good59 Reviews

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