Southern Maryland

My military husband and I move every few years, so I like to explore each new area we encounter. In Leonardtown, the St. Mary’s County seat, I happily find an historic gem filled with old-timey charm. What surprises me, however, are all the upscale draws amid that charm.

From its chic French restaurant, Café des Artistes, to its fine-art offerings at the North End Gallery, Leonardtown is ideal for a tranquil daytrip or a weekend away from the hustle and bustle of the workaday world (the town is only about 55 miles from Washington, DC).

And as for you aquatic types? You’ll love it here, too.

“A lot of people don’t realize that Leonardtown is a waterfront town,” says Mayor J. Harry “Chip” Norris. In fact, Leonardtown was named after Leonard Calvert, Maryland’s first governor, who led the Ark and the Dove on their ocean voyage from England to the New World.

What awaits me as I walk along the downtown’s brick sidewalks is a tangible sense of history, which is brought to life, in part, by the war memorial in the center of the square and the old jail museum, which displays an original cannon from the Ark.

Yet even when paying homage to big historical events, the area has a decidedly small-town feel.

“It’s like a cross between Mayberry and Annapolis,” says Joe Orlando, owner of Fenwick St. Used Books and Music.

His store—decorated with Jimi Hendrix posters and a funky Elvis clock—is a fun place to shop for books and vinyl records, especially during First Fridays, when the place thrums with live music (and when the whole downtown seems to thrum, as merchants stay open late, and special activities abound).

After perusing various first editions at Orlando’s store, it’s time for more shopping. If you’re the kind of person who treats “antique” as a verb, swing by the Maryland Antiques Center for some serious treasure hunting. And if one of your finds happens to be a vase, head over to David’s Flowers and fill it with something stunning.

There, owner David Mattingly tells me why shopping in downtown Leonardtown is far preferable to slogging through those cookie-cutter big-box stores.

“It has a boutique charm that a mall just doesn’t have,” he says simply.

It also boasts miles of waterways, which malls surely don’t have, either.

After a quick trip to McIntosh Outfitters, I head to the kayak launch and am on my way. I’m not new to paddling, but if you are, ask for some guidance from Jim Beasley, an expert guide and owner of the outfitters.

“Remember,” he warns, “you are playing in the water, so you might get wet.”

He and I go tandem in one kayak, launching from the beginning of McIntosh Run. We float beneath a canopy of trees, see a turtle jump in the water, and savor the sound of the gently lapping waves along the shore.

“If you don’t paddle too aggressively, you’ll be able to see a bald eagle perched in a tree,” Beasley says.

The run spills into the Breton Bay, where the waterway opens up and paddling becomes a challenge in the face of breezy gusts. Over at the wharf, a fabulous photo op awaits: a sun-dappled shot of the bay.

Back on dry land and hungry from all that kayaking, I consider my noshing options. Should I stop at Café des Artistes, with its fine cuisine served by locally famous chef Loic Jaffres? How about a grab-n-go lunch from the Good Earth health-food store, instead? On the other hand, Irish pub fare or some quick Mexican might hit the spot.

Decisions, decisions.

One thing I don’t have to decide, though, is when would be a good time to make a return trip to Leonardtown. It’s obvious: August 7th.

That’s when the town hosts its annual Beach Party on the Square—complete with 30 tons of trucked-in sand—a testament to the notion that live music and friendly locals are as much a part of life here as blue crabs and sailboats.

“It’s a nice kickoff to the weekend,” says event coordinator Julie Lemmon, adding that this year’s shindig coincides with First Friday.

“We’ll have a live band, a hula-hoop contest, carnival games, fireworks at the wharf, and more.

“It’s very hometown.”

But, then, so is Leonardtown. And even if you’re not lucky enough to call it your hometown, you’ll feel extremely fortunate once you come to visit.