The Eastern Shore of Chesapeake Bay in Maryland was settled only a few years after the establishment of the Virginia colony at Jamestown in 1607. Because of this region’s isolation from the mainland until bridges and tunnels were built in the mid-20th century, the land still retains a colonial environment.
A feeling of Yankee independence combined with 400 years of strong religious beliefs created old-fashioned basic values among the residents of the Eastern shore.
Many families go back generations as farmers and watermen — there is scarce else to do except for the new tourist trade. Those who make their living by fishing, crabbing and oystering on Chesapeake Bay are called watermen. People of the Earth and sea show a sensible attitude to the casual visitor.
Hooper Island and its simple isolation almost detached from the mainland depict the life of Chesapeake watermen. Situated at the end of a finger of land at the mouth of the Choptank River, the low marshlands are barely a few feet above the level of the bay.
As you approach Lands End over an arched curve of the bridge, the sea closes in on both sides. A cluster of Victorian houses stand stark-white against a hostile landscape swept by gusts of wind over the peninsula. It requires a rugged determination to live and work here. The oyster shucking sheds and small Chesapeake dredging boats laden with crab cages are testament to hard work on sea and shore.
Beached skiffs remind us of the hunting ground out in the marshes along the twisting shoreline. A few swans cruise the inlets while slim gray herons plod through the shallows searching for morsels of shellfish.
Despite the austerity, there is a welcome mood to the tranquil island. Passing islanders wave as though you were the only guests of the week.
Across the windswept inlets are undulating shorelines of pine forests and open marshes. Each outlook beckons you to explore or to jump into a sailing skiff or a crabbing longboat to cross over for a closer look at unspoiled Eastern shore architecture that is noted for its “telescope” style of Georgian or Federal architecture.
The newer frame houses were built with Charleston-style verandas to provide relief in the hot and humid summers.
Crabbing and oyster dredging are still a major industry sustaining the traditional watermen of the Chesapeake and their array of fishing craft. The picturesque skipjacks, bugeyes and skiffs were replaced by a unique longboat with a small wheelhouse and a narrow rear deck piled with crab cages or a metal dredging net.
Each inlet with a deep water port, especially off the rivers, has a small fishing village with a cluster of white Victorian clapboards or saltbox cottages and sometimes a processing plant.
The harvest of Chesapeake Bay can be found on tables in Baltimore, Philadelphia and New York City with delicious blue crab, oysters, clams and scallops. Crab is served as a steamed hard shell broken with wooden mallets, fried soft shell (in spring) and as crab cakes or balls according to each restaurant’s recipe.
For birders, Chesapeake Bay is a major stopover on the Atlantic Flyway of migratory birds on their way north, sharing space with resident osprey and bald eagles. The Blackwater National Wildlife Refuge near Cambridge has hiking trails and a drive-through route that brings birders up close to nesting and resting spots. The visitor center gives you tips for the best viewing areas.
Be sure to start your Chesapeake Bay tour in colonial Annapolis (1649) that became home to the United States Naval Academy 200 years later. The harborside seafood restaurants in historic taverns are surrounded by narrow lanes of brick row houses twisting around the historic gold-domed Maryland State House. Shopping streets fan up the hill from the harbor offering more restaurants, antiques boutiques and plenty of souvenir shops.
Access to the Eastern Shore is the Bay Bridge out of Annapolis for casual touring of pleasure boat marinas, fishing villages and more Colonial history. First stop is Old Chestertown (1706), a colonial port of wealthy merchants. The walking tour along the waterfront and into the village reveals magnificent Georgian-era brick mansions.
Farther south along the shore is the charming village of Oxford (1666). Access is across the Tred Avon River by a small-car ferry that has been in service since 1683. Just a few steps from the ferry landing is the historic Robert Morris Inn for a pleasant luncheon in a Colonial setting before strolling the shops and museums.
Don’t miss the town of St. Michaels to gorge on crab cakes, oysters, soft-shell crabs and crab cracking of the succulent blue crab of Chesapeake. There’s no substitute for Maryland crab cakes, no matter what they say elsewhere.
In St. Michaels I met the challenge of cracking a bucket of crab and then browsed the outdoor maritime museum that tells the story of the Chesapeake watermen and their boats. Bay excursions on the historic skip jack sailboats and sloops are offered here, also at Cambridge and Chestertown.
A convenient place to stay in St. Michaels is the Parsonage Inn, a B&B built in 1883 as a private residence that provides comfortable guestrooms. The location is handy for walking around the town; the Chesapeake Bay Maritime Museum is directly across the street from the Inn.
Springtime on the Eastern Shore is an ideal time to visit and avoid the humid summers and crowds of tourists.
St. Michaels displays a full array of tulips, daffodils in front yards decorated with Easter baskets and traditional egg trees.
It’s a colorful and quiet time to savor Eastern Shore hospitality combined with a lesson in Colonial history.