Sailing the Chesapeake Bay nearly four centuries ago in search of new territory for his English king, Captain John Smith wrote that "heaven and earth never agreed better to frame a place for man's habitation." The eastern side of the Bay retains today its landscape of calm despite its proximity to Baltimore and Washington, D.C.

An early-American aura pervades most of the Eastern Shore. The peninsula is rich with maritime heritage (you will see many boats!), and the area's architecture reflects its colonial and pre-colonial history (view the stately homes in Chestertown and Oxford). The Eastern Shore's first permanent English settlement—indeed the first in Maryland and one of the earliest along the Atlantic—took root on Kent Island, now Queen Anne's County, in 1631. Many Eastern Shore families have been here for generations; residents of Smith Island still speak with an Elizabethan lilt.

A visit to the Eastern Shore might consist of exploring historic sites, strolling through wildlife parks and refuges, pausing at a few of the myriad shops, dining at third-generation-owned waterfront restaurants, and overnighting at inns and bed-and-breakfasts in one of the region's enchanting communities. It you prefer the ocean to the bay, a different experience all together awaits at the popular summertime destination of Ocean City. Clinging to a narrow barrier island off the southeastern edge of Maryland's Eastern Shore, Ocean City has high-rise condos, a boardwalk, multiple restaurants and bars, and theme park-like attractions. The bustling, ocean-side culture differs dramatically from that of the Chesapeake.