Southern Maryland sporting new stops

Susan Kim

Port of Leonardtown Winery

At the picturesque Wine Cottage at Woodlawn Manor House in Ridge, Md., Tucker Grube-O’Brien will guide you through the finest bottles from Slack Winery. Not only is the tasting enjoyable, but getting yourself to the manor house inevitably involves a beautiful drive, bike, run, or hike, depending on your level of preferred adventure.

Grube-O’Brien will fill you in on the latest wine news, and “there’s a beer shack in the works,” he said, so beer lovers will want to keep an eye out, too.

Slack — which offers tastings, feasts, and live music, among other activities — has two locations to savor: Woodlawn Manor House in Ridge and Jubilee Farms in Leonardtown.

It’s best to check out the website to schedule your visit since activities can vary around harvest time.
Day trip, night trip, anytime trip

Port of Leonardtown Winery
Port of Leonardtown Winery

Slack and several other vineyards are strung out like pearls in St. Mary’s and Calvert counties in Southern Maryland. The travel stress is minimal: It’s less than a 90-minute drive from the D.C. area, but you feel like you’ve stepped back in time to a friendlier, more relaxed place.

Take the Port of Leonardtown Winery, for example. A highly unusual cooperative of 12 regional vineyards, it’s been pouring wine since 2010. One of the newest wines, Vidalacato, embodies the friendly sweetness of Southern Maryland. “We call this wine fruit cocktail in a glass,” said easygoing Stephanie Kohut, as she poured a taste. “It’s a fun wine.”

It’s a fun winery, too, offering live music on the patio as well as a winter “Wine and Dine” series.

The winery and many other restaurants and shops in Leonardtown take part in First Friday, with live entertainment, demos, receptions, hands-on activities, and seasonal promotions. If you work in D.C., you hardly have to leave work early to catch First Friday — but why not leave at noon so you can see more, taste more, and do more?

There are many more stops on the wine trail and a map is available at A good way to sample wines from Maryland is the Riverside WineFest at Sotterley Plantation, which hosts more than 20 Maryland wineries, live music, local food, kids’ activities, and an artisan marketplace.

Local breweries such as Scorpion and Mully’s are bringing the craft beer movement to Southern Maryland, as well.


One county, five state parks

St. Mary’s County is home to five state parks, including Maryland’s newest, Newtowne Neck State Park. All the parks are water-based and perfect for hiking, biking, and paddling. Less than 10 miles from Point Lookout State Park, hop aboard a Watermen Heritage tour and learn about the work of the watermen who are catching crabs, oysters, and other seafood you can enjoy at nearly every local restaurant.

And, if oysters make your taste buds go pitter patter, head for the St. Mary’s Oyster Festival Oct. 17–18. Where else can you see the U.S. National Oyster Shucking Championships and National Oyster Cook-Off?

For a unique and charming local experience, attend the tradition-laden “Blessing of the Fleet” Oct. 3–4. You can tour St. Clements Island, where the Calvert family’s settlers first landed in their new home, and the Blackstone Lighthouse, then stroll through the St. Clements Island Museum.

St. Mary’s County kicks off the holidays with the Nov. 11 Veterans Day Parade. It’s the largest in the state, featuring marching bands, military units, bagpipers, dancers, horses, Scouts, antique cars, and a wreath-laying ceremony.

And, if you want some seriously different — and wonderful — holiday shopping, check out the Amish Quilt Auction, where you can bid on quilts and other hand-stitched items in a traditional auction. It’s a great way to enter the holiday season in a place that hasn’t forgotten the meaning of friendship, small shops, and beautiful waterside relaxation.


Learn more

St. Mary’s Co. Tourism: 


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