A Look At Leonardtown

By Barbara Aiken

Arriving in Leonardtown, one almost expects Sheriff Taylor to stroll up and say, “Howdy fella, nice day ain’t it?” This little nugget of a town is a delightful glimpse into the not-so-distant past of small town America. Like Mayberry in the popular television show of the 1960s, this is a quiet yet vibrant spot filled with hometown charm and friendly folks. On the street today visually generic cars may have replaced the real cars of yesteryear, but this town is still a blast from the past.

Established around 1650, Leonardtown was first known as Newtowne. This “new town” was the second to be developed in Maryland; St. Mary’s City was the first. Nestled on Breton Bay, Newtowne was well situated with navigable deep water to the Potomac River and Chesapeake Bay beyond. In 1708 Newtowne was renamed Seymour Town for Gov. John Seymour. By 1728 it took its current name, Leonardtown to honor then Gov. Benedict Leonard Calvert, Jr. Today, Leonardtown is the county seat of St. Mary’s County and the courthouse, although not the original from 1710, is still a center of activity.

Positioned 70 miles from Annapolis, Leonardtown is a strolling town; plan on spending a casual day discovering this gem. Go online at www.leonardtown.somd.com or stop in the St. Mary’s County Division of Tourism to get your map of the walking tour, which highlights 21 sites of interest.

Georgian style Tudor Hall is the oldest building in town, where the Historical Society currently resides. If you’d like more information about Leonardtown, ask to see a copy of A Most Convenient Place by Aleck Loker, an excellent account of the area, which can be purchased locally. Nearby is the Old Jail, which was last used in 1942 and today serves as a museum. Take note of the cannon outside, which is from the “Ark,” one of the ships that brought settlers to the area in 1634. Leonardtown is proud of its town square, one of few remaining in Maryland. This is the gathering place for a variety of old-time festivals throughout the year. While there, take time to stop at the World War II Memorial and the Deceased Veterans Memorial.

There are a variety of shops, art galleries and restaurants in Leonardtown filled with delectable delights to please the discerning visitor. On Fenwick Street, visit the oldest art gallery in St. Mary’s County, the North End Gallery, filled with treasures created by an array of talented southern Maryland artists. Check out Fenwick Street Used Books and Music. This store is overflowing with tantalizing titles and hidden finds. If you’re a bibliophile, you will have a hard time extracting yourself from this book lover’s haven.

Housed in an 1857 historic brick building, the oldest on Washington St., Caught My Eye showcases intriguing wares from India, local crafts and repurposed treasures. Also on Washington Street, try Crazy for Ewe, which specializes in superb yarns and patterns for those who enjoy knitting or crocheting, and The Fuzzy Farmer’s Market, which offers shawls, scarves, bags, baskets and other items made from a variety of wools.

When you’re ready to relax and have a leisurely lunch, Café des Artistes has some of the best offerings in town including local wines. As you enter you may be delighted by the garlic aroma of my favorite, Les Escargots au Vin Blanc. On an agreeable day, dine outside and enjoy the wafting breeze.

Another great spot for lunch is The Front Porch on Washington Street. This cozy restaurant was formerly the Sterling family home. Try the crab cake sandwich for a scrumptious treat or the cheese platter paired with a glass of wine.

Now that you’ve had time to relax and enjoy some fine dining, how about a walk? Head down the hill to the rippling waters of Breton Bay to take in Leonardtown Wharf. You may spot a majestic eagle or elegant great blue heron.  There are benches for sitting and this makes an excellent spot for an al fresco lunch. Maybe you could get dessert to go and enjoy it as you gaze out over the peaceful view. If anyone has concerns about walking you may want to drive down to the wharf, as the walk back is very steep.

After a day of exploration you’ll feel caught in a time warp. In your mind’s eye, you’ll see Sherriff Taylor waving goodbye and maybe saying, “Now ya’ll come back now, ya hear?”

Barbara is very fond of Leonardtown and visits regularly. She can be reached at  [email protected].


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