Wineries & Distilleries
Discover where bourbon first started and where grapes for wine were first planted in Maryland! Taste the history here in St. Mary's County.
Spend a weekend tasting your way through St. Mary's County's craft beverages! Try award-winning wines at Port of Leonardtown Winery, learn how bourbon started in St. Mary's County at Tobacco Barn Distillery, enjoy fresh cocktails made from the flavored moonshine at Southern Trail Distillery and hear the amazing stories of how local families started their wineries at Generations Vineyard and Xella Winery.
Want more craft beverage fun? Make sure to check out our Event Page for future events like live music at the wineries, pop up markets at our distilleries, Beerfest at Historic St. Mary's City, Wine Fest at Historic Sotterley, and more!
Ready to get tasting?
- Generations Vineyard - Tasting room is open Fridays from 5 p.m. - 8 p.m. and Saturdays from noon to 5 p.m. You can also schedule an appointments.
- Port of Leonardtown Winery - Tasting room is open 7 days a week, noon to 6 p.m. And noon til 9 p.m. on the first Friday of the month.
- Southern Trail Distillery - Tasting room is open Thursdays - Sundays from 10 a.m. - 5 p.m.
- Tobacco Barn Distillery - Tasting room is open Saturdays from 11 a.m. - 5 p.m., Sundays from 11 a.m. - 4 p.m., and you can book appointments for Monday - Fridays.
- Xella Winery - Tasting room is open on Saturdays from noon to 5 p.m.
For those who don't have tasting rooms, you can find these craft beverages at:
- Purchase bottles from Jubliee Farm Fermentations at the Home Grown Farm Market on Saturdays from 9 a.m. - 1 p.m.
- Pair your dining experience with a delicious cider Free State Cider at Social Coffeehouse, The Slice House, Taphouse 1637, and Old Line Restaurant and Pub. You can also pay them a visit at the Home Grown Farm Market on Saturdays from 9 a.m. - 1 p.m.