Centrally located, Leonardtown serves as a convenient hub for shopping and dining.

Shopping, dining, a winery, a quaint town square, and a water trail along Breton Bay offer fun for all ages. Newtowne Neck State Park is not far from the town at the end of Route 243. The park offers opportunities for paddling Breton Bay and the Potomac River, as well as for hiking, birding, and hunting. Adjacent to the park is St. Francis Xavier Church which is part of the Religious Freedom National Scenic Byway.

Town of Leonardtown

Leonardtown received its moniker “a most convenient place” back in the early 18th century. The county’s courthouse, hospital, and governmental center are located here. Shops, galleries, and restaurants are located around the quaint town square and along Fenwick Street and Route 5. There is an in-town hotel, a waterfront park, and a winery. Historic sites are Tudor Hall which houses the St. Mary’s County Historical Society, and the Old Jail Museum. Leonardtown holds numerous weekend events including First Fridays.

First Fridays in Leonardtown

The town of Leonardtown welcomes you from 5-8 PM for shopping, dinner, drinks, and dessert on the First Friday of every month.

Restaurants are open with both indoor and outdoor dining and many shops, stores, and galleries are open late with special exhibits.

Enjoy dinner at one of the many local restaurants, enjoy a drink from Social Coffeehouse or Antoinette's Garden, explore Shepherd's Old Field Market, shop at one of the many local shops and art galleries, and enjoy a sweet treat from Heritage Chocolates!

Click on the link below for monthly First Friday specials, activities, and future dates!

First Fridays Event Page


Leonardtown's activities, including a winery, a wharf, and historical sites, means you will always find something to do. Ride the free Leonardtown Trolley during the summer months for easy access to all the shopping, dining, and activities the town has to offer!

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