Across the Chesapeake Bay Bridge, life slows down. Turn off Route 50 or Hwy. 301 and go down a country road past cornfields. Pause by rivers and marshes where birds and rustling grass are the only sounds. Stop in small towns where mom-and-pop shops still thrive. If you love to watch trees light up with fireflies on a summer night, or cycle down a country lane, or let the breeze take your boat past farms as old as America, you'll love the Eastern Shore.
Easton is the Eastern Shore's Colonial capital -- its roots are evident on every picturesque street. It is the capital of Talbot County, home to three waterfront communities within easy driving distance. Waterfront St. Michaels has the most shops as well as the Chesapeake Bay Maritime Museum. Boaters clog the harbor on summer weekends, but in spring and fall or midweek in summer, its charms are more accessible. Oxford is quieter, but it's attractive for its slower pace, waterfront park, and garden-bedecked streets. Tilghman (my favorite place!) hasn't bothered to beautify for the tourists -- but its unique waterman's lifestyle is enough to draw them.
Cambridge, on the Choptank River, is beginning to capture the attention it deserves with the introduction of new lodging and the early stages of a downtown renaissance. Its history and outdoor activities make it worthwhile.
The southern areas of the Eastern Shore, including Smith Island and Crisfield, are the ultimate in waterman villages. Change comes slowly to these remote parts of Maryland, and residents like it that way. That very attitude draws visitors to these hard-to-reach spots.
North of the Bay Bridge, Chestertown is not only a Colonial town with leafy streets and elegant homes, but it's also a college town. George Washington permitted the college founders to use his name for Washington College. A dozen miles away is Rock Hall, a waterfront village with marinas and seafood restaurants.
Farther north is Chesapeake City, on the Chesapeake & Delaware Canal, which remains a crossroads for the marine traffic using the canal every day.