6 Best Wineries Near Middleburg, VA

Middleburg, Virginia is a historic town located in Loudoun County in Northern Virginia. It is conveniently located on Route 50, and it is less than an hour’s drive from Fairfax County.

Middleburg is home to many of the best wineries in the state, including several award winners. This makes it an excellent destination for wine lovers!

Below are some of my top recommendations for wineries near Middleburg, VA. Also, be sure to check out some of my other favorite Northern Virginia Wineries!

Please note that the information on this page is subject to change, so I recommend visiting the winery website or giving them a call to confirm the most up-to-date information before you visit.

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Top Photo by Luca J on Unsplash.


Table of Contents


Want to learn about the EASIEST way to visit some of the best wineries in Virginia? Check out my recommendations for The Best Virginia Wine Bus Tours!


A Map of Wineries Near Middleburg, VA


Where to Stay in Middleburg, VA
Red Fox Inn & TavernGreat for historic charm
* * *
Salamander Resort and SpaGreat for a luxurious getaway

Greenhill Winery and Vineyards (Middleburg, VA)

Location:

Greenhill Winery and Vineyards is one of my personal favorite wineries to visit in Middleburg, VA. Their wines are excellent and robust, particularly their reds, and they have a lovely outdoor setting with rolling hills and a large pond nearby for taking a walk. They’re also very dog friendly.

Top wines at Greenhill include “Blanc de Blancs”, which is a lovely sparkling wine; Petit Manseng Reserve; and “Superstition.”

Hours:

May to September:

Monday – Thursday: 12pm – 6pm

Friday, Saturday, Sunday: 12pm – 7pm

October to April:

Daily: 12pm – 6pm

Food:

Charcuterie platters for purchase. You can bring your own food to eat in the outside areas only. 

Dogs Allowed?

Yes.


Chrysalis Vineyards

Location:

39025 John Mosby Hwy, Middleburg, VA 20117

Chrysalis Vineyards is another excellent winery in Middleburg. They feature a full menu, plus they’re open seven days a week, which is a nice bonus. They primarily focus on wines derived from Norton grapes, which are very common in Virginia. In fact, they have 40 acres of Norton vines, which is the largest planting of Norton in the world.

Hours:

Monday – Thursday: 12pm – 6pm

Friday – Saturday: 12pm – 8pm

Sunday: 12pm – 7pm

Food:

They have a full menu, including bruschetta, spinach dip, charcuterie boards, pizzas, paninis, and salads.

Dogs Allowed?

Yes, but only outside the building. 


Boxwood Estate Winery

Location:

2042 Burrland Ln, Middleburg, VA 20117

Boxwood Winery is owned by John Kent Cooke, the former owner and president of the NFL Washington football team and a collector of French wines.

The winery is comprised of 26.5 acres, and it specializes in Merlot, Cabernet, Cabernet Sauvignon, Petit Verdot, Malbec, and Sauvignon Blanc.

Hours:

Wednesday – Sunday: 11 am – 6 pm

Food:

They have cheese boards and baguettes, baguette sandwiches, dips, and more small plates.

Dogs Allowed?

No.


Otium Cellars

Location:

18050 Tranquility Rd, Purcellville, VA 20132

Otium Cellars is located a little further afield in Purcellville, VA, which is about 15 miles north of Middleburg. It is a boutique winery that also hosts private events at the Tranquility Farm, which also boasts Loudoun County’s historic landmark silo.

Guests can also stay overnight at the Grüner Bungalow, which accomodates up to 18 guests in an 8 bedroom, 8 bathroom house.

Hours:

Monday: 11 am – 6 pm

Tuesday: Closed

Wednesday: Closed

Thursday: 11 am – 6 pm

Friday: 11 am – 9 pm

Saturday and Sunday: 11 am – 6 pm

Food:

They have a delicious menu, which includes dishes like Leg of Lamb French Dip with Au Jus, Lobster Salad and Jumbo Lump Crab over Fried Heirloom Tomatoes, and Brick Oven Pizzas.

Dogs Allowed?

Yes, but only outside, not in the tasting room.


Cana Vineyards and Winery of Middleburg

Location:

38600 John Mosby Hwy, Middleburg, VA 20117

Cana Vineyards and Winery is a family-owned farm winery located in a lovely building with a huge wraparound outdoor terrace and covered gazebo. It’s a perfect location for enjoying a wine tasting.

The vineyard has won numerous awards for their wines.

Cana Vineyards has live music on select Saturdays. They also host weddings and other special events.

Note that wine tastings are available by reservation on Saturdays and Sundays and last about 35 to 45 minutes.

Hours:

Monday: 12 pm – 6 pm

Tuesday: Closed

Wednesday: Closed

Thursday: 12 pm – 6 pm

Friday: 12 pm – 6 pm

Saturday: 11 am – 6 pm

Sunday:  12 pm – 6 pm

Food:

They have crackers, cheese, charcuterie, and spreads for sale. You can also bring your own food for a picnic.

Dogs Allowed?

Yes, in the public areas of the ground level, in the Sunset Pavilion, and around the grounds.


50 West Vineyards

Location:

39060 John Mosby Hwy, Middleburg, VA 20117

50 West Vineyards is just a short drive away from both Cana Vineyards and Chrysalis Vineyards, so it’s easy and convenient to make a stop at all three on a day of wine tours!

The vineyard features lovely views of the nearby Bull Run mountain range. They have a covered patio, picnic tables, and fire pits.

They also won the 2022 Gold-Medal Winner at the Governor’s Cup, as well as the Governor’s Case Winner.

Hours:

Monday and Thursday: 12 pm – 5 pm

Tuesday and Wednesday: Closed

Friday: 12 pm – 6 pm

Saturday and Sunday: 11 am – 6 pm

Food:

You can bring your own food for a picnic.

Dogs Allowed?

Yes, dogs are allowed on the grounds, but not in the tasting room.


Where to Stay

Salamander Resort and Spa (Source: Agoda.com)

Red Fox Inn & TavernGreat for historic charm

The Red Fox Inn & Tavern is a gorgeous hotel conveniently located in downtown Middleburg and close to many restaurants. It is brimming with historic brick charm. The hotel features a restaurant, bar, garden, free WiFi, and a terrace.


Salamander Resort and SpaGreat for a luxurious getaway

The Salamander Resort and Spa is a top-notch accommodation with a restaurant, bar, seasonal outdoor pool, fitness center, tennis courts, and spa center. The resort also features a hot tub, sauna, and steam room. The rooms have private balconies.

The resort is located on an incredible 340 acres and features gorgeous views at the foothills of the Blue Ridge Mountains.

Guests can even enjoy activities like horse riding and cycling onsite.


Interested in learning more about my favorite wineries in Virginia?

Learn more about my favorite Luray Wineries, Northern Virginia Wineries, Charlottesville Wineries, and Chesapeake Wineries!


Learn more about the Best Virginia Wine Bus Tours

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