Things to do in Leonardtown
One of the main reasons why Leonardtown truly stands out is its vibrant Arts and Entertainment (A&E) District. As the heart of the town’s cultural scene, the A & E District offers a variety of artistic and entertainment venues that cater to all tastes. From galleries showcasing works by local artists, to intimate spaces for musicians and singers to perform, the A&E District is the perfect place to ignite your passions. Immerse yourself in Leonardtown’s rich history, as the A & E District is home to historic and well-preserved buildings like the Old Jail Museum and St. Mary’s County Historical Society.
Check upcoming events and activities here.
On the first Friday of every month, Leonardtown comes alive with an incredible mix of art, music, gourmet food, shopping, and family-friendly fun. The streets buzz with activities, offering something new and exciting upon every visit. Here are a few reasons why First Friday in Leonardtown will make you fall in love with this incredible place:
Nestled in the heart of Leonardtown, the Port of Leonardtown Winery is the perfect spot to gather with friends and family, learn about wine-making, and, of course, enjoy some delicious local wines! This co-operative winery, run by a collective of 12 different vineyards, produces over 20 varieties of delectable wines. It's the perfect place to relax and unwind on weekends.
Not only does the winery offer a vast selection of award-winning wines, but it also hosts events throughout the year, including live music and food-and-wine pairings. Come discover the fun and toast a glass of wine!!
Step into the world of top-notch entertainment at Action Lounge and Billiards featuring a variety of gaming options like pool, shuffleboard, darts, and a fantastic arcade sections. You deserve a relaxing evening filled with laughter, delicious food, and great drinks. Action Lounge masters the recipe for a perfect night out. Their menu boasts a wide variety of mouthwatering dishes made from fresh, locally-sourced ingredients. Plus, their impressive selection of craft beers will introduce you to new flavors that you won't want to miss.As you experience the thrill of the games, this captivating place also offers a spacious lounge, friendly staff, and an admirable calendar of events and activities that keep the fun going all year round.
Nestled along the gleaming waters of Breton Bay, Leonardtown Wharf is a paradise for those who wish to escape the hustle and bustle of city life and enjoy nature's beauty in a serene environment. The wharf, which was once an active steamship port in the early 20th century, has been transformed into a vibrant recreational park and marina. Here, you will find an assortment of activities to suit everyone's tastes and preferences.Spend the day visiting its scenic waterfront with breathtaking vistas. Rent a canoe or kayak for the day, or take a stand-up paddleboard class for an experience on the water. Don't forget to wander down the boardwalk and soak in the beauty of this one-of-a-kind Maryland region.