Leonardtown, Maryland, is a small town with a big personality, where history, creativity, and community come together on the banks of Breton Bay. Stroll the charming Town Square, one of Maryland’s few remaining squares, lined with specialty shops, cafés, and locally owned boutiques. Sip coffee while admiring the war memorial garden, catch a local artist at work, or relax on a sunny bench watching the day unfold. The town thrives on events that draw visitors from near and far. From First Fridays and Summer Music Festival concerts to themed movie nights, Veterans Day parades, and the festive Christmas on the Square, Leonardtown knows how to celebrate its history, arts, and people. Outdoor adventure is never far away. Leonardtown Wharf Waterfront Park and the Port of Leonardtown Park provide kayaking, paddleboarding, walking trails, picnic spots, and serene views of the water. With ambitious waterfront projects and a thriving arts scene, Leonardtown blends small-town charm, creativity, and scenic beauty into an unforgettable escape. #Americasfavoritesmalltowns
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Leonardtown
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