Leonardtown is a charming, walkable county seat on the St. Mary’s River with a lively downtown full of cafés, galleries, restaurants and seasonal festivals, plus easy waterfront recreation — perfect for multi‑week stays if you want small‑town calm with plenty of weekend options and a friendly local scene.
Within easy drives are Solomons Island (marinas, waterfront dining and summer events), the Lexington Park/Patuxent River NAS area (larger retail, dining and outdoor trails), and Annapolis/the Chesapeake Bay corridor for bigger‑city dining and sailing day trips under 75 miles.