Things to do in Leonardtown

Leonardtown is a warm and friendly town with so much to offer. Whether you’re looking for a place to call home or just want to explore, Leonardtown has plenty of activities and attractions to explore. With its historic buildings, great restaurants, and unique shops, there is no shortage of things to do. From outdoor activities like fishing and kayaking to indoor activities like visiting museums or attending festivals, Leonardtown has something for everyone. So come explore the best of what this charming town has to offer!

Maryland's Arts & Entertainment Districts | VisitMaryland.org

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.

Leonardtown | Visit Leonardtown MDOn 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:

Unwind and Relax with Music and Art
First Fridays are all about showcasing local talent, and you'll find plenty of it in Leonardtown. Live music performances by various artists fill the streets as you stroll through a multitude of galleries featuring local art.
Taste the Flavors of Leonardtown
Indulge your taste buds in some of the finest gourmet food available. From festive food trucks to exquisite dining options, First Friday offers a culinary adventure that can satisfy the most demanding of palates.
Shop Local
One of the many great things to do in Leonardtown is to support local businesses. First Friday is the perfect opportunity to explore charming shops and boutiques that line the streets, offering unique, quality items that can't be found elsewhere.
Family-Friendly Fun
Bring the whole family and create lasting memories as you engage in activities specially curated for all ages. From crafts and sidewalk chalk art to bouncy castles and face painting, First Friday ensures fun for everyone!
Mark your calendars! Check out the upcoming event themes to discover how living in Leonardtown can be a joy!



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.