The Downtown and Upcountry Wineries and Vineyards You Have to Visit

From lively Downtown wineries to the Agricultural Reserve of Upcountry, Montgomery County, Maryland is the perfect place to spend an afternoon sampling award-winning wines just outside Washington, DC. Whether you consider yourself a wine aficionado or recently discovered a newfound interest in wine tasting, plan a visit to savor local artisanal wines.


Olney Winery: Olney

Sourcing high-quality grapes from California, Chile, South Africa, Germany, and Italy, Olney Winery gives you a taste of the world in every glass. With more than 34 different award-winning wines, the tasting room offers a sampling selection of any five wines for $8 and is open seven days a week.

Urban Winery: Silver Spring

Looking for unique nightlife plans? Urban Winery was the first winery in the region to be located in an urban environment. Winemaking is a family tradition for the owner of Greek-descent, so it’s no wonder that an array of flavorful Mezze is offered to accompany their $15, $13, and $10 five wine flights tastings.

Olney Winery in Olney, MD.


Rocklands Farm Winery & Market: Poolesville

By utilizing low-impact, biological processes within their 9.5-acre vineyard, Rocklands Farm Winery & Market cultivates healthy vines and soil, resulting in high-quality fruit for their handcrafted, small-batch wines. Schedule a guided weekday tour to see their practices in action and be sure to try their $14 wine tasting featuring a selection of six wines.

Sugarloaf Mountain Vineyard: Dickerson

Sugarloaf Mountain Vineyard’s trained staff specializes in wine education. Whether on a weekend winery tour or enjoying a $10 sampling in the tasting room, Sugarloaf Mountain Winery guides you through every step of their award-winning wines. Afterwards, order a glass of your favorite to accompany a snack from their a la carte menu and cozy up next to a firepit.

Great Shoals Winery: Takoma Park

Great Shoals Winery sources fruits from local and regional farms to produce their high-quality craft wines and ciders. Showcasing a full range of flavors, sample any six wines and/or ciders from their selection of 30 award-winning products with their $10 tasting package.

Looking for other libations in Montgomery County, Maryland? Check out these local distilleries and breweries.