By Bob Tagert

With spring right around the corner, we thought we would take a road trip to Leonardtown, Maryland, which is in and is the county seat of St. Mary’s County. For many years, Leonardtown has been famous for sponsoring the annual oyster-shucking championships that are held annually at the St. Mary’s County fairgrounds. Although most of Southern Maryland is surrounded by water, the only water access to Leonardtown is Breton Bay which leads to the Potomac River.

In 1708 Phillip Lynes, then Mayor of St. Mary’s City, Maryland’s colonial capital, designated fifty acres of land at the head of “Brittons Bay” to be divided into 100 lots. He further ordered that one lot be set aside for a courthouse to be built at an expense not to exceed 12,000 pounds of tobacco. Maryland’s history of the tobacco trade is preserved today with the preservation of many tobacco barns that dot the countryside. Twenty years later this plot of land was named Leonard Town in honor of Benedict Leonard Calvert, who was Maryland’s governor during this period. In the decades that followed, Leonard Town became the place where local residents conducted their official business with the colony. Farm products were regularly shipped through the port at Breton Bay.

Today, Historic Leonardtown (the names were combined during the Civil War) remains the only incorporated municipality in St. Mary’s County with its own elected mayor and town council. The town is experiencing a renaissance of its downtown as witnessed by the recent openings of several new restaurants and businesses, some which are located in historic buildings. Keeping it traditional, there is an order Mennonite farming community located a few miles to the northwest, where community members sell furniture, crafts, produce, and other homemade/homegrown products. The ever changing Leonardtown Wharf is open as a public attraction for both locals and tourists. Facilities for boating, kayaking and canoeing are in place and future additions are in the works. The latest “beautification” project is the creation of murals on the alley side of buildings in the market square area. While still in the making, our favorite is the “Alice in Leonardtown” piece. All artwork is done by local artists and depict the many nuances of the town.

I grew up in Prince Georges County and would take motorcycle rides to southern Maryland in the late 60’s and Leonardtown was always a good stop on our way to Point Lookout at the confluence of the Potomac River and the Chesapeake Bay. The town still has the same charm today as then but the buildup of housing and new businesses in the town has added a more sophisticated element.

Leonardtown was recently named one of the 15 Best Small Towns in Maryland for a Weekend Escape by VirginiaTravelTips.com. A few years ago, the Leonardtown marketing gurus embarked on a First Friday campaign which has proved very successful and with the recent opening of The Inn at Leonardtown there are now accommodations right in town and across from the town square where all of the entertainment and activities are staged. The Inn is unassuming from the outside but very welcoming and comfortable on the inside and the staff are very helpful. The room rate includes an extensive “Do It Yourself” breakfast bar and there is a gift shop with local treasures next to the lobby.

A good place to start your visit is the Visitors Center which is housed in the Old Jail Museum. The Old Jail was constructed in 1876 and remained in use until 1945. Operated by the oldest sheriff’s office in the country, this granite block and brick structure retains its original cells and rooms.

A short walk from the Old Jail House will put you in the middle of Leonardtown Square. Surrounding the Square are specialty shops, art studios and restaurants. You can find original works of art by local artists at the North End Gallery or the St. Mary’s Arts Council Gallery & Gift Shop. You can also try your hand and create your own work of art at the instructor-led art studios like The Yellow Line, Board & Brush and Wine & Design.

On the Square are three restaurants. The first discussed is Ye Old Town Cafe. This is down home eating out at its best. The Cafe opens early for breakfast and then serves lunch until 2pm. Next to the Cafe is The REX, the brain child of Joe Kurley. The building is a former theater, and Kurley and his partners plan to renovate the theater after the restaurant has established itself. The REX doesn’t open until 3 pm and is open until 2 am. The REX serves comfort food and has a great bar. The third restaurant on the Square is SWEETBAY Restaurant & Bar. This is a bit more upscale in nature and offers a variety of choices with a concentration on continental cuisine. Also on the Square is Antoinette’s Garden a popular Gourmet Coffee and Wine Cafe. Formerly on the Square but now a block down Washington Street is Heritage Chocolates, home of handmade chocolates and confections. We had some fantastic pizza from The Slice House II Go that is also located on Washington Street.

Around the corner from the Square on Fenwick Street you will find SOCIAL, a Coffeehouse & Cocktail Bar. They have a line waiting for coffee but you can still find a seat at the bar and their Irish Coffee is killer. The SOCIAL will move to the Square in the next few months. Further up on Washington Street you can find The Front Porch restaurant with Old Town Pub across the street. Both local favorites.

The above is a small sampling of the cuisine available in Leonardtown and the surrounding area. There is something for every palate.

A few blocks off the Square behind the Fire Station you can find Sheperd’s Old Field Market (SOF Market). A historic warehouse and hardware store were renovated into an indoor marketplace and community gathering space. SOF Market’s name is derived from the “Sheperd” family, who donated their land in the 1600’s to help create portions of current day Leonardtown. The market has over 80 participants where you can browse and shop a variety of gift and home decor. It is truly a neat place to visit and I will bet you will buy something. We have yet to get out of there without buying something. At the back of SOF you will find the Brudergarten aka Bru where local craft beers are served in addition to popular bottle beers, spirits, wines and specialty cocktails. Bru doesn’t open until 4 pm and has become a popular destination and gathering place.

A short drive from the heart of Leonardtown you can find the Port of Leonardtown Winery on the perimeter of the town. This winery is owned by the Southern Maryland Wine Growers Cooperative, a group of 12 vineyards located throughout Southern Maryland. The winery is located at the McIntosh Run Park right next to McIntosh Run.

McIntosh Run is a stream that runs through the park to Breton Bay. McIntosh Run Trail has four access points and provides paddlers with the opportunity to explore the quiet marshes of Leonardtown or the open waters of Breton Bay. As you enter Breton Bay the whole area opens up and in a short time you will arrive at The Leonardtown Wharf which is at the end of Washington Street.

The wooded area between McIntosh Run and the town is the 400 acres that has been set aside for future development. That will be another road trip in the future.

This is a very condensed overview of Leonardtown – the parts that I am personally familiar with – and I encourage you to make it a destination in your future travels. In addition to Leonardtown, there is much to explore in St. Mary’s County…St. Mary’s City, St. Mary’s College, St. Clements Island, Piney Point Lighthouse and much more. The drive is about an hour’s time but will take you back hundreds of years. Spring is here…take a road trip.