History & Museums
- Historic St. Mary’s City Museum of History & Archaeology
- St. Mary’s City
- Calvert Marine Museum
- Pax River Naval Air Museum
- Civil War Sites
- Memorial Honoring Enslaved People in Southern Maryland
- Captain John Smith Chesapeake National Historic Trail
Parks & Outdoors
- Point Lookout State Park
- St. Clement’s Island State Park
- Newtowne Neck State Park
- Piney Point Lighthouse Park
- Solomons Island
On the Water
Wine, Spirits & Local Flavor
- Port of Leonardtown Winery
- Xella Winery
- Tobacco Barn Distillery
- Trossbach Produce Stand
- Buzzy’s Country Store
Arts & Entertainment
- North End Gallery
- Newtowne Players (community theater)
- St. Mary’s Summer River Concert Series
- Escape from the Past — Southern Maryland’s Original Escape Room