12 Best Wineries near Poolesville

Rocklands Farm Winery Winery • $$
14531 Montevideo Rd, Poolesville

“This little gem is our go-to winery year-round. While their hours are limited during the winter, Saturdays there (whether you spend them in the tasting room or outdoors by an open fire) are a treat. Good wines, friendly staff, and the best atmosphere of any winery in the area.“

4.7 Superb218 Reviews
The Crossvines Bistros • $$
16601 W Willard Rd, Poolesville

Customers` Favorites

Steak and Eggs
Chicken Wings
Poutine

“2026 Update-

My original review was regarding the poolesville golf course before it became crossvines. The new owner has done a fantastic job with the property. The course is in great condition now, the new restaraunt and social area is awesome. Really happy with the transformation of the property here and highly recommend for golf or just a night out for dinner and drinks.“

4.2 Good119 Reviews
Droumavalla Farms Winery Winery •
15066 Limestone School Rd, Leesburg - 5.92 miles

“My friend and I spent several hours here this Sunday afternoon, to unwind from the week. The blond-wood winery / tasting room is beautiful and calming, and the wine is delicious (especially the Petit Verdot). Lisa Michelle and Eddie were warm, hospitable, and down to earth from the moment we arrived. They periodically checked on us to keep our tasting going smoothly, yet still left us to our own conversation. The views, even now in February, are stunning. Loudoun County has many wonderful wineries; this is a true gem!“

5 Superb37 Reviews
Bleu Frog Vineyards & Ole Bleu Brewery Winery • $$
16413 James Monroe Hwy, Leesburg - 6.79 miles

“First visit today. Lovely venue. Nice wine and food. Kids and pets…witnessed a couple with 3 dogs who had no control over them. One pet fight with another dog guest. Then witnessed a small child having her hand bitten by one of the dogs. I hope the owners of the winery have sufficient insurance to allow anyone…especially children and babies, and dogs to enjoy the venue. Great to be family and pet friendly…but is that a wise business decision? Not sure that alcohol, children and pets are a wise and safe business practice…what happened to baby and pet sitters for an afternoon out?“

4.6 Superb108 Reviews
Loudoun Cider House Winery •
43376 Spinks Ferry Rd, Leesburg - 6.2 miles

“We had the pleasure of attending Loudoun Cider’s Grand Opening, and they even hired our Marigold Bus & Booth for the celebration! I couldn’t be happier for Macy and her family — what an incredible addition to Loudoun County.

If you’re looking for a beautiful spot to unwind, Loudoun Cider is a must-visit. The venue is scenic, the cider is top-notch, and the whole experience just feels special. From the owners to the staff, everything is run with such care and heart.

Can’t wait to go back and sip some more cider soon!“

4.9 Superb33 Reviews
Tarara Summer Concert Series Wineries • $$
13648 Tarara Ln, Leesburg - 7.09 miles

“Great venue for a wine and listening to your favorite music either from 80s or 90s or whats in the concert series.
Enjoyed the Bon Jovi tribute band.
Bring your own chair and food and enjoy the great wine they have to offer“

4.5 Superb41 Reviews
Hidden Brook Winery Wineries • $$
43301 Spinks Ferry Rd, Leesburg - 6.21 miles

“Great little winery,Great wine selection, especially loved the cab sav and the unusual chardonnay.Very good food selection as well, and a huge shout out to Angle, our hostess and sumalie (I'm probably misspelling it) for such a great service and making our visit so fun“

4.2 Good29 Reviews
Fabbioli Cellars Wineries • $$
15669 Limestone School Rd, Leesburg - 6.04 miles

“Love the pairings! Such a fun vibe and fantastic wine!“

4.2 Good60 Reviews
Sugarloaf Mountain Vineyard Wineries • $$
18125 Comus Rd, Dickerson - 7.53 miles

“This was a cute spot. The vibe is great and the wine is delicious. Such a gorgeous drive out and the staff was very friendly. I went during a super slow time so I didn't get to experience a lot of their fun stuff but I had the chance the relax and enjoy the view, which I appreciated very much!“

4.1 Good54 Reviews
Eagletree Farm Winery & Restaurant Wine Bar • $$
15100 Harrison Hill Ln, Leesburg - 5.5 miles

Customers` Favorites

Bombay Chicken Curry
Flatbreads
Chardonnay
Risotto
Salads
Pizza

“Just had the best night at Eagletree with a friend. Jeff and Lori were so kind and generous and made the dining experience so wonderful. The food was amazing but the experience was even better!“

4.5 Superb97 Reviews
Windridge Vineyards Wineries •
15700 Darnestown Rd, Darnestown - 5.13 miles

“Excellent experience. We enjoy ☺️“

3.9 Good167 Reviews
Cooper’s Hawk Winery & Restaurant American • $$
19870 Belmont Chase Dr, Ashburn - 6.59 miles

Customers` Favorites

Cooper's Hawk Chicken Giardiniera
Crispy Brussels Sprouts Bin 72
Cooper's Hawk Calamari Bin 73
Cooper's Hawk Chocolate Cake
Cooper's Hawk Chicken Caesar
Salted Caramel Creme Brulee
House-Made Meatballs Bin 90
Chicken Potstickers Bin 73
Pistachio-Crusted Grouper
Braised Short Rib Risotto

“Hey guys it's me again from my favorite restaurant Cooper's Hawk Winery & Restaurant Ashburn, Virginia. The family and I are having a great time Friday night, the food was amazing, and the wine is off the charts . Thank you, Ms. Norris, and Staff.“

4 Good910 Reviews

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