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FEATURED EVENTS FEATURED EVENTS VALENTINE39S DAY IN LEONARDTOWN VALENTINE39S DAY IN LEONARDTOWN Discover All There is to Love About Leonardtown Valentine39s Day Features Discover All There is to Love About Leonardtown Valentine39s Day Features 10 Things We Just Love in Leonardtown This Valentine39s Day Weekend Sample Valentine39s Day Date Itineraries 10 Things We Just Love in Leonardtown This Valentine39s Day Weekend Sample Valentine39s Day Date Itineraries Shop Eat Stay Events Explore Plan Business LTown Trolley LEONARDTOWN Welcome to The LeonardtownButterfly Trail A Small Southern Maryland Town that39s Big on Charm Welcome to Leonardtown a small community in the heart of St. Marys County Maryland. This charming walkable Town is known for its beautiful landscapes breathtaking waterways and friendly welcoming people. When you enter Leonardtown youll be transported back in time as you take in the quaint Town Square and Historic buildings but Leonardtown is undergoing a current renaissance of its downtown area with the addition of an eclectic mix of specialty shops galleries and worldclass restaurants.