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Longstreet Highroad Guide to the Chesapeake Bay

By Deane Winegar

Design by Lenz, Inc. Decatur, Georgia.



Chesapeake Bay > The Eastern Shore: Maryland

The Eastern Shore: Maryland

The words Eastern Shore bring to mind a land of marshes, unbroken expanses of wild rice, loblolly pine forests, villages of hardy watermen, grand waterfront estates of ship captains, and the midnight calls of migrating geese, ducks, and swans. This version of the Eastern Shore does exist, but a traveler sometimes has to go out of the way to find it.Click here for a new window with a large version of this map.

The Eastern Shore is comprised of several Maryland and Virginia counties located on what is called the Delmarva Peninsula, separated from the mainland to the west by the Chesapeake Bay, and washed by Delaware Bay and the Atlantic Ocean on the east. In addition to portions of Maryland and Virginia, the peninsula also contains the entire state of Delaware—hence the tri-state name, Delmarva.

Two modern bridges across the Chesapeake Bay now span the gap both physically and culturally between the Eastern Shore and the mainland of Maryland and Virginia. In 1952, the 4-mile William Preston Lane Jr. Memorial Bridge (usually called the Bay Bridge) replaced the ferry between Annapolis on the western shore and Queen Anne’s County on the Eastern Shore. The 17.6-mile Chesapeake Bay Bridge-Tunnel at the mouth of the bay brought the nearly forgotten southern tip of Virginia’s Eastern Shore in contact with mainland Virginia at Norfolk when it opened to traffic in 1964. With the bridges have come affluence, development, and new ideas, spilling out as from a cornucopia to this once isolated and fiercely conservative land.

Those who cruise north up the Chesapeake Bay may find themselves imagining how the land on this peninsula looked to early explorers. Captain John Smith, who left Jamestown in 1608 to explore the bay, named the Eastern Shore. He sailed north as far as the Sassafras River, which separates Cecil and Kent counties on what came to be called the Upper Shore.

Some 23 years later, people with a spirit of adventure began one of the Eastern Shore’s first permanent settlements on Kent Island, the largest island in the Chesapeake Bay, and now part of Queen Anne’s County. Surrounded by rich fishing waters, and with soil suitable for many kinds of farming beneath their feet, these pioneers began a long tradition of making a living from the sea and the soil, with little reliance on outsiders.

Other fishermen and farmers began to populate "The Shore" as it is known locally. But with no way to keep in touch with the outside world but by boat, people developed their own culture and traditions. The hardy individualism and even the British accent can still be found among the descendants of the first settlers. Generally, they reside in small fishing villages and on farms away from the city of Salisbury, Maryland, away from the resort town of Ocean City, Maryland, and away from the bridges and modern highways that are synonymous with change.

Maryland’s claim to the Eastern Shore lies in the southeastern part of Cecil County (described in the previous section on Head of the Chesapeake Bay) and in the counties of (from north to south) Kent, Queen Anne’s, Caroline, Talbot, Dorchester, Wicomico, Somerset, and Worcester.

Several major waterways and innumerable tributaries wind their way through the lowlands of Maryland’s Eastern Shore, offering abundant recreation opportunities to those equipped with fishing rods, crabbing gear, canoes, sailboats, motorboats, yachts, water-skis, Jet Skis, duck calls, binoculars, or cameras.

Major ports of call, full-service marinas, and a liberal sprinkling of boat ramps offer access to the rockfish, catfish, bass, pickerel, crappie, crabs, oysters, clams, and other riches of Eastern Shore waters. Many rivers and creeks take their colorful names from the Native Americans who fished these waters before white settlers arrived—names such as Choptank, Nanticoke, Wicomico, Manokin, Big Annemessex, and Pocomoke.

Highways on the peninsula are mostly level and many have wide, paved shoulders. Bicyclists, walkers, and joggers enjoy exploring the countryside using the designated shoulders, passing fields of soybeans, corn, tomatoes, peas, beans, cucumbers, cantaloupes, and melons.

Nature lovers, hikers, and bird watchers can find solitude in the wetlands and forested uplands of the abundant parks, preserves, wildlife management areas, and refuges on Maryland’s Eastern Shore. Among the most well-known natural areas are the Eastern Neck Island National Wildlife Refuge (Kent County), the Horsehead Wetlands Center of the Wildfowl Trust of North America (Queen Anne’s County), Blackwater National Wildlife Refuge (Dorchester County), Pocomoke River State Park (Worcester County), and Assateague Island National Seashore (Worcester County).

An incredible number of wildlife management areas—18 in the southern four counties of Maryland’s Eastern Shore alone—provide habitat for birds and animals on islands, in the reeds and rushes of tidal wetlands, and in the oak and loblolly pine forests.

Tourist Facilities such as restaurants and lodging can be found, among other places, at Chestertown in Kent County, in the Kent Island area of Queen Anne’s County, in Easton and St. Michaels in Talbot County, in Cambridge in Dorchester County, in Salisbury in Wicomico County, in Princess Anne in Somerset County, and in Pocomoke City and Ocean City in Worcester County.

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