This winery with nearly 10,000 vines scattered alongside the Patuxent River has a tasting room that once housed tobacco and cows. The owners focus on grapes like Chardonel and Chambourcin. Seasonal wines that incorporate blackberries and blueberries grown among the vines are quick sellers. 

The Robin Hill plot has been a farm since 1829, and owner Susan Watson-White’s family has been working it since 1955. As part of a settlement funded by the state, the owners stopped growing that cash crop and used the government funds to turn their attention to grapes. Watson-White, a “Miss Maryland Tobacco Queen” in 1985, serves wines that have won more than 50 medals in various competitions in the past few years, including an award for Maryland Winery of the Year in 2019 in the New York International Wine Competition. Before taking a seat on the tasting room’s expansive porch, ask to see the bottling room and kegs of rare port. Then try the Pi’Goat Blanc, a sweet rosé with hints of strawberries and cherries.

Co-founder Ryan Vierheller’s family counts seven generations of hooch-making history, including Prohibition-era bootleggers in Stafford County, Virginia. Today BlueDyer makes gold and dark rum, bourbon and rye whiskey, gin, and gluten-free sugar cane vodka. High char oak barrels provide an oak and wood flavor to the signature gold rum. The distillery gives tours from 5 p.m. to 10 p.m. Tuesdsay through Friday, and 2 p.m. to 10 p.m. on Saturday and Sunday.

Cindy and Jason Mullikin founded this craft brewery that cans every 500-gallon batch of beer. There are more than a dozen taps, too, with bar stools offering a view of the brewers at work. All-year options include a blood orange blonde ale and a hazy IPA. Heat-seekers should try a small-batch habanero stout.

A Tuscan-style mansion looks over former tobacco fields that span 291 acres of vines. Chambourcin aged in oak barrels is a popular dessert wine, and wine slushies are perfect on a hot day. An adjacent Southern Maryland Biergarten .

Tobacco Barn Distillery manages 17 acres of corn that goes into its whiskeys and bourbons, and nearby farms send ingredients for rums. Even the distillery’s electricity is hyperlocal, drawn from solar panels and a geothermal system on the property. After three years of aging, select barrels of Tobacco Barn’s rum are sent aboard the historic U.S.S. Constellation in Baltimore’s Inner Harbor, picking up flavor from fluctuating temperatures and gentle rocking on the water. The facility makes sure to point out a history of whiskey distilling in Southern Maryland that predates Kentucky and Virginia. Basil Hayden, Sr., the “Old-Grand” himself, was part of the Catholic community in St. Mary’s County before settling in Kentucky.

Owner Sahil “Sunny” Malhotra boasts 26 taps and a selection of 100 beers at this California, Maryland, bar. IPAs, lagers, and brown ales include many small releases from across the U.S., including What Maryland Does, an imperial IPA from True Respite Brewing Company in Derwood, Maryland. A comprehensive martini list has a popular pineapple upside down cake flavor. A broad food menu lists crab dip, fried pickled tacos, grilled mahi mahi, and lamb quesadillas. The 1637 in the name refers to the year St. Mary’s County was established.  

Known for its rosé, Port of Leonardtown is an annual leader in Maryland Governor’s Cup competitions. Winemaker Lauren Zimmerman incorporates grapes from a cooperative of 12 vineyards across Charles, Calvert, and St. Mary’s counties. POL also regularly hosts karaoke nights and food trucks.