Welcome to Leonardtown, a small community in the heart of St. Mary’s County, Maryland. This charming, walkable Town is known for its beautiful landscapes, breathtaking waterways, and friendly, welcoming people. When you enter Leonardtown, you’ll 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 world-class restaurants. As the only Arts & Entertainment District in Southern Maryland, Leonardtown offers a rich experience in culture where you can explore art galleries, see shows and attend art shares with upcoming and prominent artists, take group or one-on-one art classes, and create your own work of art in instructor-led workshops. We invite you to visit Leonardtown to experience the charm, the excitement and the warmth first-hand, and if you've been away, we welcome you back. You're always welcome! 

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Begin planning your visit on this site. Explore all the amazing sites, learn the wonderful things there are to do, discover fine dining, eclectic shopping and exciting arts & entertainment we offer, and more. We look forward to your visit.