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The region south of Annapolis and D.C. is a peninsula broken in two by the Patuxent River, a 110-mi-long tributary to the Bay. Until the middle of the 20th century, the so-called Western Shore was the main vacation spot for families from Baltimore and Washington. When the Bay Bridge was completed in the 1950s and people could easily get to shore points like Rehoboth and Bethany Beach, towns like North Beach and Chesapeake Beach fell out of favor. However, in recent years the closer-in "Western Shore" has become popular again.
Annapolis. People in Annapolis live to sail on the Chesapeake Bay; its picturesque harbor with hundreds of boats is the epicenter of town. Add the Naval Academy and you have a definite nautical theme. The town is a lovely warren of historic homes and quaint shops.
Calvert County. Like the calm, nearly wave-free Bay itself, the shore resorts of Calvert County are tranquil getaways. Relatively undiscovered, Calvert County lacks the boardwalk life of the ocean resorts and its towns are often just collections of fishermen's cottages and holiday homes.
St. Mary's County. Across the Governor Thomas Johnson Bridge from Calvert County's Solomons Island is St. Mary's City, once (briefly) the capital of Maryland. The historic city is gradually being restored, and is the center point of the mostly rural county.
Charles County. Charles County is slowly becoming a bedroom community to Washington, D.C.—especially for those who want acres and acres of land and don't mind a long commute. But there's still plenty of relatively unspoiled parkland.