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Top 11 Best Wineries to Visit in Southern Maryland

From sunny beaches in the east to mountain retreats in the west, with busy urban hubs and miles of sprawling farmland in between, Maryland has something for everyone. The spring and fall seasons are especially beautiful and are the perfect time to explore the many wineries and vineyards located throughout the state. Southern Maryland, in particular, is full of wines (and wineries) that offer unique flavors alongside one-of-a-kind experiences.

Here are the 11 best wineries in Southern Maryland to visit.

1. Port of Leonardtown Winery

23190 Newtowne Neck Rd, Leonardtown, MD 20650
St. Mary’s County is home to some of the oldest cities and most famous historic sites in Maryland. In addition to exploring the rich history of Southern Maryland, as of 2010, visitors to St. Mary’s County can enjoy wines from 12 cooperative area vineyards at the Port of Leonardtown Winery. This southern Maryland winery offers one-of-a-kind events, year-round. Vino and Vases allows guests to show off their creative side as they sip, weekends are full of music and family fun, and the food truck selection rotates regularly.

2. Xella Winery and Vineyard

26781 Laurel Grove Road, Mechanicsville, MD 20659
This small family farm winery opened in 2007 and is owned and operated by Les and Erin Melanson who discovered their mutual love of wine early-on in their relationship and dreamed of someday opening their own vineyard and winery in southern Maryland. Thirteen years later their dreams became a reality and everything about their brand tells a story.

The name Xella is an acronym of the first letters of each family members’ name (Xenia, Erin, Lester III, Lester IV, and Amara) and their bold, well-balanced, clean wines make it easy to understand exactly how the grapes are grown. Furthermore, their sustainable, biodynamic, and regenerative farming practices make Xella Winery and Vineyard even more unique and well-loved by the community.

3. Robin Hill Farm and Vineyards

15800 Croom Road, Brandywine, MD 20613
Robin Hill Farm & Vineyards has passed down its legacy and traditions as a family farm since 1955. The farm has an agricultural history of tobacco, hogs, nursery, pumpkins, agritourism, and now…vineyards. Their farming philosophy, which includes sustainable, humane practices, has landed them a spot in the Maryland Governor’s Agricultural Hall of Fame.

For years the farm operated as a producer only, but in 2017 they opened their doors as one of southern Maryland’s wineries as well. Visitors are invited to stop by the farm, taste the wine, and relax while enjoying stunning countryside views.

4. The Vineyards at Dodon

391 Dodon Road, Davidsonville, MD, 21035
One of the largest wineries in southern Maryland, the Vineyards at Dodon grows mainly international vinifera varieties – Merlot, Cabernet Franc, Cabernet Sauvignon, Petit Verdot, Sauvignon Blanc and Chardonnay – and has more than 28,000 vines densely planted over 16 acres in three adjacent vineyards. There are no recipes for making Dodon wines.

Methods are adapted to each lot in an effort to create the right conditions for the wine to express the site and vintage. Hillside picnic tables with gorgeous views are available to reserve for weekend wine-tastings.

5. Janemark Winery & Vineyard

15200 Baden Naylor Road, Brandywine, MD 20613
Jane and Mark Vogt, the husband-and-wife founders of Janemark Winery & Vineyard, developed a passion for wine early on in their marriage. They began planting vines on a family farm in 2013 and expanded their operation a year later. Varietals including Vidal, Chambourcin, Barbera, and Albarino can all be enjoyed at the Tasting Barn which dates to the 1930s.

Janemark offers a variety of tasting options – wine tasting kits, bottles, glasses and more can all be purchased and enjoyed in their outdoor seating section. Weekends bring food trucks and music, making this the perfect spot for a relaxing afternoon.

6. Romano Vineyard and Winery

15715 Bald Eagle School Road, Brandywine, MD 20613
The Romano Vineyard and Winery in southern Maryland was founded in 2007 by Joseph and Jo-Ann Romano, but it all started as a family farm full of honeybees. The family has been keeping bees and harvesting honey since 1998. In 2006 they decided to give grape growing and winemaking a try. The first grapes were harvested in 2008 and 2009.

Today the vineyard is home to five wine grape varietals – Chambourcin, Barbera, Vidal, Cayuga, and Traminette.

7. Generations Vineyard

22715 Wheatleys Content Farm Lane Leonardtown, MD 20650
Generations Vineyard is a small family owned and operated vineyard in Leonardtown, MD. The vineyard is part of Wheatleys Content Farm which has been around for years, and until recently the family hadn’t hoped to count themselves among the distinguished wineries in southern Maryland. But, in 2012, the latest generation of family sisters caught the farming bug and Generations Vineyard was born.

Walk-ins are welcome in the tasting room, and group tastings are available by reservation. Weekends at Generations are full of local music and delicious food truck eats, while weeknights bring unique events like bouquet making and yoga in the yard.

8. Running Hare Vineyard

150 Adelina Rd, Prince Frederick, MD 20678
The Tasting Room at Running Hare Vineyard is the perfect place to enjoy a glass of wine paired with beautiful scenery and live music on the weekends! Wood fired pizza is available on site from Pizza Di Vigna, as is Hispanic and American cuisine from Hungry Hare, making for the perfect happy hour experience. If wine isn’t your thing, Running Hare is also home to Southern Maryland Biergarten which also offers events for the entire family.

9. Gemeny Winery and Vineyards

8606 Cedarville Road, Brandywine, Maryland 20613
Gemeny Winery and Vineyards is located on a 200-acre working family farm in Southern Prince George’s County. Just 17 miles from the Capital Building in Washington D.C., this winery is the brainchild of Gordon and Mary Gemeny. The vineyards are surrounded by fields of grain and lush woods, providing the perfect spot to enjoy a gorgeous Maryland afternoon. Plus, the indoor tasting room offers not just sips and flights, but wine slushies, too! What’s not to love?

10. Thanksgiving Farm Vineyards and Winery

195 Harwood Road, Harwood, Maryland 20776
The farmhouse at Thanksgiving Farm was built in 1893, was systematically restored in 2004, and in 2007 was listed on the National Register of Historic Places by the U.S. Department of the Interior. Thanksgiving Farm Vineyards & Winery in southern Maryland is family owned and operated and specializes in the production of European-style dry wines. All wines are made exclusively from grapes grown in the vineyards and are produced in the fall, after harvest. Check out their to-go wine tasting flights which can be enjoyed in the outdoor seating section on weekends, or brought home for a special night in any day of the week.

11. Windridge Vineyards

15700 Darnestown Road, Darnestown, MD 20874
Windridge Vineyards is a family-owned company that believes wineries in southern Maryland should strive to ensure their wine reflects the unique terroir of the vineyard from which it comes. Their first vines were planted in 2011, but since the family has been farming in Montgomery County since 1959, they have intimate knowledge of the land which helps them select the most suitable acreage for grape production, as well as the best grapes for each vineyard site.

Reservations are recommended but walk-in groups of up to 8 people are allowed on a first come, first served basis.

Stay at The Hotel at the University of Maryland for Your Wine Getaway

Located in College Park, MD, and near many wineries in Southern Maryland, The Hotel at UMD is the perfect spot to start your weekend (or longer!) Maryland wine getaway. Take advantage of our Relax and Recharge special which includes plush robes and slippers for the ultimate in cozy comfort, a sound and aromatherapy machine for a delightful nights’ sleep in one of our luxurious guest rooms, free parking, late checkout, and discounted meals at Bagels & Grinds and Potomac Pizza – both located inside The Hotel.


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