Racing out of Washington DC on a high-speed multilane freeway, US-50 accesses one of the state’s most popular destinations, the colonial Chesapeake Bay port town of Annapolis.

From Annapolis, heading toward the Atlantic coast and the massively popular beach resort of Ocean City, the final leg of US-50’s 3,200-mile transcontinental trek is a mad dash across 100 miles of Maryland’s Eastern Shore.

This is one of the more captivating areas in the northeastern United States, but the four-lane US-50 freeway doesn’t encourage sightseeing. If you want to get a feel for the real Eastern Shore of piney woods, cornfields, and fishing fleets, you’ll have to follow the many back roads and search out the many historic towns and villages—many of which we point out as worthwhile detours, including some that are among the oldest and most carefully preserved in the nation.

Map of the Loneliest Road through Maryland.
Map of the Loneliest Road through Maryland.