Maryland's Eastern Shore shares the Delmarva Peninsula stretching southward from easternmost Pennsylvania with virtually all of Delaware and with the two counties of Virginia's Eastern Shore. Although Maryland's eight Eastern Shore counties share a similar culture as well as their early history, traveling through them reveals individual characteristics unique to each.
To understand the Eastern Shore, look to the Bay. The Chesapeake is 195 mi long and the nation's largest estuary (a semi-enclosed body of water with free connection to the open sea). Freshwater tributaries large and small flow south and west into the Bay, ensuring the agricultural wealth of the peninsula as well as the bounty of the Bay ("Chesapeake" is an Algonquian word meaning "great shellfish"). At day's end look west across the Chesapeake Bay and you can see the sun set over water—a rare sight for any East Coast resident.
The Bay Bridge, just past Annapolis on Route 50, is both the entry point and a bottleneck to the Eastern Shore communities. It is not unusual for hours long backups, especially on summer weekends.
Cecil County. The northern gateway to the Eastern Shore caps the headwaters of the Chesapeake Bay, including some 12,000 acres of park- and forestland as well as a National Resource Area of more than 5,600 acres. It is known best, however, for its world-renowned horse farms.
Kent County. Immediately to the south of Cecil County lies a delightful blend of agriculture and maritime culture. The principal towns here are successful combinations of colonial-era history and 21st-century modernity.
Queen Anne's County. Best known as the eastern gateway to Maryland's Eastern Shore, Queen Anne's Kent Island is the site of the eastern end of the double-span William Preston Lane Jr. Bridge—known colloquially as the "Bay Bridge." On the island's eastern shore, Kent Narrows, with its variety of lodging, restaurant, and water-related recreation opportunities has emerged as an attractive travel destination.
Talbot County. Much of this county is threaded with waterways of various sizes that yield myriad untrammeled peninsulas and almost-islands that welcome explorers. Its county seat, Easton, is a vibrant small town.
Dorchester County. Dorchester exudes an aura of gentility reminiscent of the Southern states. Home of one of the region's largest wildlife refuges, it, too, has a wildly ragged western shoreline, undeveloped and unsung, and a mix of agriculture and maritime heritage.
Lower Eastern Shore. Maryland's southernmost shore comprises three counties: Wicomico, whose county seat, Salisbury, is the area's second-largest port city (after Baltimore); Worcester, which includes the ever-popular year-round Atlantic resort destination Ocean City; and quiet Somerset, with the state's southernmost locales (opposite the mouth of the Potomac River).