Leonardtown, United States offers 4 beaches perfect for sunbathing, surfing, swimming, and more. Leonardtown is known for the Port of Leonardtown Winery and the annual Maryland International Raceway events. The best time to travel to Leonardtown, United States, is in late spring (May), when the average air temperature is around 70°F (21°C) and the water temperature is approximately 65°F (18°C). Sandee provides detailed maps, photos, and reviews from fellow beachgoers to help you Choose Your Beach™ and plan your perfect beach vacation!