Southern Exposure

History lives on in Charles and St. Mary’s Counties

Story by Julekha Dash

Soak up the water views and step back in time in Southern Maryland. Charles and St. Mary’s counties are replete with historical treasures that offer a glimpse of life during the 17th century, along with parks, restaurants and other sites that hug the water along the Chesapeake Bay.

Make the two-plus hour drive from D.C. or Baltimore to St. Mary’s City, which was once Maryland’s capital. A must-see is one of Southern Maryland’s top tourist attractions, Historic St. Mary’s City. Declared a national landmark in 1969, it is a living history and archaeological museum. Stroll the streets to mingle with actors recreating life during the 17th century. The museum’s annual events include the Historic St. Mary’s Beer Fest in June, with craft beer, local food vendors and artisan wares.

The Maryland Dove is a recreated 17th century tall ship that will teach you all about maritime life. A plaque at the site honors Mathias de Sousa, an indentured servant and the first African-American to serve in Maryland’s General Assembly. You can meet the fictional Godiah Spray family, tour their home and garden, and learn about tobacco farming.

About an hour north in Charles County, Port Tobacco Historic Village contains three buildings overlooking the Port Tobacco River. Tours of the Port Tobacco Courthouse, Stagg Hall and Burch House offer a glimpse into the town that was once Maryland’s second largest seaport.

Drinking locally produced wine and spirits is another way to capture the area’s flavor. Rye whiskey was first developed in St. Mary’s and descendants from the area later migrated to Kentucky and Tennessee to produce the area’s famous brown liquor.

Tobacco Barn Distillery is reviving the rye whiskey tradition in Hollywood, about 30 minutes south of St. Mary’s City. The establishment prides itself for being a “ground-to-glass” distillery and grows the corn used for its bourbon and whiskies on the farm.

Resume your 1812 tour 15 minutes south in Leonardtown, attacked by British troops as part of a series of raids along the Potomac. A wayside marker at the scenic Leonardtown Wharf Park recounts the story. It’s a short walk to colorful galleries and antique shops downtown. These include Leonardtown Vintage Market, Opal Fine Art Gallery & Gifts and North End Gallery, the oldest gallery in St. Mary’s County. Complete your gallery hopping with a visit to the Leonardtown Arts Center, a collection of artists’ studios where you can purchase jewelry, paintings and other items created on site.

No visit to Leonardtown would be complete without a stop at the Port of Leonardtown Winery, a cooperative of 12 vineyards from St. Mary’s, Calvert, Charles and Kent counties.

Here’s a list of places to eat, drink, shop and sightsee in Charles and St. Mary’s counties.


Port of Leonardtown Winery
23190 Newtowne Neck Road, Leonardtown
St. Mary’s first commercial winery, Port of Leonardtown is a cooperative winery with vineyards from St. Mary’s, Calvert, Charles and Kent counties.

BlueDyer Distilling
52 Industrial Park #15, Waldorf
This Charles County distillery offers tours and tastings of its rum, whiskey and gin.

Tobacco Barn Distillery
24460 Hollywood Road, Hollywood
Tobacco Barn produces whiskeys with corn from its farm and makes rums using molasses from Baltimore’s Domino Sugar.


Ruddy Duck Seafood and Alehouse
16800 Piney Point Road, Piney Point
Offering unparalleled views of the Potomac River and St. George Creek, Ruddy Duck provides the perfect escape while enjoying a local catch on its waterfront deck. Beers like the Wildflower, brewed with brown rice and honey, are brewed in house.

Elements Eatery & Mixology
46580 Expedition Drive, Lexington Park
The seasonal restaurant and cocktail bar sources its meats, seafood and vegetables from Maryland farms and suppliers. It also donates a portion of its sales to feed and house those in need.

The Front Porch
22770 Washington Street, Leonardtown
Located in a gracious historic home with a covered porch, the two-floor restaurant showcases local wines, produce and seafood on its menu.


Island Inn & Suites
16810 Piney Point Road, Piney Point
Located next to the Ruddy Duck Seafood & Alehouse on St. George Island, the 28-room, all-suite waterfront hotel is a boutique brand from Choice Hotels International. Rooms come with balconies, refrigerators and microwaves.

Inn at Brome Howard
18281 Rosecroft Road, St. Mary’s City
Built in 1840, the historic mansion was once a residence of the Howard family and a piece of a tobacco and wheat plantation. Located on the grounds of Historic St. Mary’s City, the grounds offer views of St. Mary’s River.

Victorian Candle B&B
25065 Peregrine Way, Hollywood
Nicknamed “The Castle,” the eight-room Victorian-style B&B is decorated with maple floors and cabinets made from wood grown in the county.

St. Michael’s Manor
50200 St. Michaels Manor Way, Scotland
Each of the four rooms offer a water view of the Long Neck Creek. Don’t leave without tasting the five varieties of red and white wine grown on the estate’s three-acre winery.


Point Lookout State Park, Civil War Museum & Lighthouse
11175 Point Lookout Road, Scotland
Head to the southern tip of St. Mary’s County where the state park offers hiking trails, a beach and a nature center and museum open May through October.

Historic St. Mary’s City
18751 Hogaboom Lane, St. Mary’s City
The living history museum allows visitors to immerse themselves in 17th century life in Maryland’s first capital with guided tours, workshops and costumed actors who recount the stories of the town’s early settlers.

Port Tobacco Historic Village
8450 Commerce Street, Port Tobacco
Tour the site’s three historic buildings, located on the Port Tobacco River, which recount the town’s role in the Civil and Revolutionary wars



Leonardtown Arts Center
22660 Washington Street, Second Floor, Leonardtown
Watch jewelers, painters and other artists in action and then buy the goods afterwards.

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