The past is never far away from the present among the coves, rivers, and creeks of the Chesapeake Bay's lesser-known western shore. In the lively port of Annapolis, Colonial Maryland continues to assert itself. Today "Crabtown," as the state capital is sometimes called, has one of the highest concentrations of 18th-century buildings in the nation, including more than 50 that predate the Revolutionary War.

The region's counties—Anne Arundel, Calvert, Charles, and St. Mary's—have been supported since their 17th-century founding through tobacco fields and fishing fleets. More recently, the northern parts of the counties have emerged as prime residential satellites for the Annapolis–Baltimore–D.C. metro triangle; but despite the subdivisions and concomitant shopping centers, southern Maryland maintains much of its rural character. With the exception of the fair-weather getaway enclave Solomons Island and the archaeological site-in-progress Historic St. Mary's City, the region remains largely undiscovered. All the better for travelers who come to enjoy stunning water vistas, miles of scenic roads, dozens of historic sites, and a plethora of inns and bed-and-breakfasts on the water, in tiny towns, and in the fields and woodlands of its unspoiled countryside.