Wineries in Upperville, VA

Barrel Oak Winery and Brewery welcomes our members and guests! Enjoy our award-winning wine, beer, food & beverage, and vendors. Host your event with us today

Willowcroft boasts breathless panoramic views of Loudoun Valley and the Blue Ridge Mountains. Willowcroft’s personal attention to detail, both in the vineyard and the winery, has resulted in national award-winning wines, time after time. In the 1800s the slopes were recognized f…

Stone Tower Winery is a family-owned and operated winery, where our magnificent views and premium wines are equally matched by impeccable hospitality. Working with a team of top-notch viticulturists, soil specialists, and oenologists, we've created 95 acres of stunning vineyard…

From the hills of Middleburg, 50 West is a vineyard & tasting room owned and operated by Sunset Hill