Leonardtown, Maryland – “A Most Convenient Place”

By Bob Tagert

Leonardtown, Maryland – “A Most Convenient Place”

With all of the heat we have endured this past month we thought we would keep the road trip close to home and take a nice hour-and-a-half drive to Leonardtown, in Southern Maryland. You can take the road most traveled and drive down Route 5 in Maryland or take Indianhead Highway (Rte 210) south and pick out some of the Scenic Maryland back roads to your destination.

Leonardtown is the County Seat of St. Mary’s County. Although the town has had a growth spurt in the last decade, the town has managed to hold on to that small town charm year round. With so much to do so close at hand, it is no wonder Leonardtown earned its antebellum moniker, “A most convenient place.” Just a short drive from Alexandria and D.C., wineries, galleries, dining, history and more make Leonardtown a great getaway.

In the early 2000’s this little burg undertook a beautification program that included a redesign of the main street and waterfront in town. Widening the street and installing a beautiful landscaped median as well as new sidewalks that lead to the waterfront boardwalk and wetlands preserve at The Wharf have heightened the impact on the senses as you drive down the street.

Leonardtown is home to Southern Maryland’s only Arts & Entertainment District. The A&E District celebrated its Arts and Entertainment District Designation on First Friday, September 6, 2013 becoming the first of its kind in Southern Maryland. Celebrated the first Friday of every month in Leonardtown Square from 5 PM – 8 PM, local entertainment is provided as well as merchant specials and refreshments. Experience art inside their galleries and outside in the square. Live demonstrations and Plein Air painting. Just last month the 20th annual Potomac Jazz & Seafood Festival was expanded to include Leonardtown in addition to the main Saturday concert at Colton Point.

The Leonardtown Wharf gives you the opportunity to rent kayaks, canoes and paddle boards on Breton Bay which flows into the Potomac River. The Wharf is relatively new to this historical town and has extended the boundaries of what the town has to offer. The Beach Party on the Square August 3rd will extend from the square to the wharf. There will be fire truck hose downs, a party band, strolling entertainers, “Running of the Balls” and 40 tons of sand! If these 100 degree days continue, this will be a major treat!

In the heart of town is the Old Jail Museum which was built in 1858 and in use until 1942. The granite block and brick structure retains its original appearance. On the other side of town is the recently opened Shepherd’s Old Field Market (SOF Market). You can browse through over 40 shops and services in this “mini-mall’. SOF Market has something for everyone…maybe not what you need, but certainly what you might want! One of the anchors of the Market is a beer and wine garden. Although they do not brew their own beer at the Brudergarten Beer Garden, they do showcase the other local brews made in St. Mary’s County. They also feature a selection of spirits for a little stiffer drink and special cocktails. The fenced in outdoor space offers corn hole, life-sized Jenga, ladder golf and other games. From what we learned, it has quickly become a popular gathering spot for locals. There were several on their way in the door when we were leaving around Happy Hour time.

There are a number of dining establishments that serve a variety of foods in Leonardtown. From southern cuisine at the Front Porch Restaurant to Asian Fusion at Jessie’s Kitchen to home cooking and breakfast at Ye Olde Towne Cafe. If your taste leans towards Mexican there is Dos Amigos Mexican Grill and Smokey Joe’s for a BBQ fix. The night life kicks in at places like The REX, Olde Town Pub and a secretive Speakeasy. Each of these places offer food and a relaxing after hours ambiance. The Social Coffeehouse and Speakeasy is a particular treat. A coffee shop by day, at 4 PM the bookcase swings open and the back room bar comes into play. A very novel idea, this place has been a hit since it opened. New owners Sean and Lisa are downplaying the speakeasy part so that folks won’t think it is so secretive, it still feels like you have entered somewhere special when you walk in – check out the candles when you are in there. They offer light bites, seasonal cocktails and a selection of very good rum, bourbon and cinnamon whiskey from Tobacco Barn Distillery located in nearby Hollywood, Maryland.

In a non-descript red brick building on the square you will see the sign for Heritage Chocolates. Once through the door you are in a whole new world. The large, brightly lit store has comfortable seating, a viewing window as they make chocolates (think of the popular I Love Lucy episode) and displays of their wares. Heritage Chocolates was established in 2015 and has brought handmade chocolates and confections to Southern Maryland. Initially the menu offered classic chocolates and candies including caramels, brittles and toffees. The line expanded to include graham crackers, caramel apples and cream-filled chocolates. Today the kitchen produces over 75 unique recipes. They also have their own gelato which we found to be very refreshing on a hot day.

A short distance out of the main part of town and along McIntosh Run is Port of Leonardtown Winery, a cooperative of Maryland vineyards partnered with the wine making skills of the winery. This makes Port of Leonardtown unique to Maryland in that all of the fruit is grown in Maryland. The wines are not only creative, but very good. This is a great place for a picnic in the park and you can also rent kayaks next door at Patuxent Adventure Center and paddle down McIntosh Run into Breton Bay and end up at the Wharf.

As you can tell, most of the events and entertainment in Leonardtown are centered around The Square and down to The Wharf. On September 14th The Square will host the 13th Annual Taste of St. Mary’s. Sample menu favorites from St. Mary’s County restaurants and caterers. There is also live music. On September 20th-22nd events move to the County Fairgrounds for the St. Mary’s County Fair.

On October 6th the Antique Tractor & Truck Parade returns to The Square. On October 19th & 20th the 53rd Annual St. Mary’s Oyster Festival is held at the Fairgrounds just outside of Leonardtown. Celebrate the opening of oyster season on the Chesapeake Bay and take part in one of the oldest and most popular oyster festivals in the United States featuring the U.S. National Oyster Shucking Championships and National Oyster Cook-Off. Known for its exquisite range of seafood and exhibition of cultural activities surrounding oysters and the waterman’s way of life in St. Mary’s County, this annual festival also includes live music, local foods, arts, crafts, craft beer tastings, and family fun.

As you can see, there is quite a bit to do in Leonardtown and we only touched on a bit of what happens in the whole of St. Mary’s County. There is a ton of history in this little town that I didn’t touch on, but that would take up a whole other column. The real treat though is the people you will meet. Always friendly people, but also, people set in their ways and customs. Situated between the Patuxent River and the Potomac River, St. Mary’s County is steeped in history and Leonardtown stands in the middle of it all – you might say that is genuinely “A Most Convenient Place”. Escape the city heat and take a road trip to Leonardtown and the cool byways and waters of St. Mary’s County.

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