St. Mary's City, MD

With historic St. Mary’s City, St. Mary’s College of Maryland and Maryland Dove nearby to visit, you’ll want to plan to spend a full day exploring. (The Maryland Dove is a re-creation of a late 17th-century vessel commemorating the Dove of 1634, which accompanied Lord Baltimore’s original expedition to Maryland.)

Each August St. Mary’s College hosts 300 to 400 boats from the Governor’s Cup Race (and the famous party afterwards), the largest sailing race on the East Coast. The overnight race begins in Annapolis and culminates in a whole day of festivities at St. Mary’s City. (The fastest vessels complete the entire 73-mile stretch in less than 7 hours.)

Should you crave more exploration, the reconstructed 17th century Godiah Spray Tobacco Plantation, part of Historic St. Mary’s City, is the site of the original colony of Maryland. It is located at the headwaters of Milburn Creek off St. Inigoes Creek.