Leonardtown is the county seat of St. Mary's County, set on the inland side of Breton Bay in Southern Maryland. It is small, tidy, and more interesting than its size suggests: the courthouse square, old jail, galleries, shops, and waterfront give it the feel of a working county town that has learned to make room for visitors without turning itself into a museum.
The centre is the best place to start. The Old Jail Museum tells a compact local history story, while the surrounding streets hold antique shops, studios, and cafes. The hill down to Leonardtown Wharf opens onto Breton Bay, with a boardwalk, kayak access, and the sort of wide water view that explains why the Chesapeake shapes so much of Maryland life.
Leonardtown works best as a slow stop on a Southern Maryland drive rather than a full-scale destination. Pair the town centre with a paddle on McIntosh Run or a tasting at the Port of Leonardtown Winery, then continue toward St. Mary's City, Point Lookout, or the Potomac-side villages further south.