Eastern Shore Road Trip

from The Most Scenic Drives in America

4. Wye Island Natural Resources Management Area
As a side trip, drive west on Rte. 50 a few miles, then follow signs to the turnoff south to Wye Island Natural Resources Management area, located in the tidal rescesses of the Chesapeake Bay between the Wye and the Wye East rivers. It is a prime spot to observe migratory waterfowl and shore birds in their native habitats.

Returning to Rte. 662, the drive takes what seems to be an indecisive course, weaving its way back and forth across Rte. 50—the Main Street of the Eastern Shore, with the traffic to prove it—on its way south to the town of Easton, which dates to Revolutionary times.

5. Easton
Clapboard houses and white picket fences line narrow, shady streets in Easton, gateway to the Chesapeake Bay. For a scenic detour that offers a wind-in-the-hair view of the bay, ramble down Rte. 333 to Oxford.

Once rivaling Annapolis among pre-Revolutionary ports, Oxford saw many tons of tobacco and grain (and, on a somber note, slaves and convicts) pass through its customs house. A replica of the original building stands down by the Tred Avon River, where the landing for the Oxford–Bellevue Ferry (nine-car limit) beckons to travelers. (A ferry has operated here since 1683; the first owner accepted tobacco for fares.) On the other side, motor up to the picturesque village of St. Michaels, whose harbor on the Miles River is crowded with sleek yachts. For a detailed view of the town’s seagoing legacy, visit the famed Chesapeake Bay Maritime Museum; it features everything from an old lighthouse and waterfowl decoys to historic bay boats.

Follow Rte. 33 down the narrow neck of land known locally as Bay Hundred Peninsula to Tilghman Island, connected to the mainland by a tiny drawbridge. Here you get a wide-angle view of the vast blue-gray waters of the Chesapeake Bay, America’s largest estuary. Crab huts are scattered here and there on the windblown island’s shores, home to hardy fishermen who for generations have sought blue crabs, oysters, clams, and other treasures in the bay’s salty depths. After sampling the local harvest transformed into such succulent delights as crab cakes and soft-shell crab sandwiches (or eaten steamed), backtrack to Easton on Rte. 33 and head south on Rte. 50 into Cambridge.

6. Cambridge
This old port dates from the 1680s, but the earliest buildings that survive here are the elegant Georgian- and Federal-style homes that line High Street. The street slopes down to the town wharf, which commands a beautiful view of the Choptank River. Eight miles southwest of town, poised serenely on the banks of Church Creek, lies the Old Trinity Episcopal Church, erected in the late 1600s. Built with money from the royal pocketbook, this brick chapel (one of the nation’s oldest in continuous use) is surrounded by a fascinating old graveyard.

7. Blackwater National Wildlife Refuge

In a land obsessed with goose hunting, where marksmanship is highly esteemed and decoys decorate mailboxes, migrating geese are in need of a safe haven. Consequently, each year legions of these birds flock to the enormous Blackwater National Wildlife Refuge, where they can hide out in peace. The maze of marshy channels and woodlands provides a year-round home for many other birds as well. For a close-up view, take the sinuous five-mile Wildlife Drive into the heart of the preserve, which recalls the tidewater scenery witnessed by Eastern Shore settlers some three centuries ago.

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    Most Scenic Drives in America

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