Eastern Shore Road Trip

So named because it abuts the eastern margin of the Chesapeake Bay, Maryland’s Eastern Shore is endowed with scores of inlets, bays, rivers, and canals. Even the livelihoods (farming and fishing) and pastimes (hunting and sailing) of those who live here reflect the Eastern Shore’s age-old interplay between land and water.

1. Chesapeake City
Beginning at the town of Elkton, the drive cruises south on Rte. 213 toward Chesapeake City, or Canal Town, as it is known locally. There the highway soars across a bridge high above the Chesapeake and Delaware Canal, which connects the Chesapeake Bay with the Delaware Bay—a shortcut to the Atlantic Ocean. Completed in 1829, the waterway saves oceangoing vessels a 300-mile journey south, then north, around the tip of the Delmarva Peninsula.

Chesapeake City itself consists of a restored tavern, general store, and pastel saltbox houses where canal builders once lived. At the edge of town, near an inlet dotted with sailboats, the Chesapeake & Delaware Canal Museum houses a fine collection of canal memorabilia. The museum is perched right on the bank of the canal, and visitors can watch giant barges led by tugboats and ocean freighters ply the placid waters.

2. Chestertown
Continuing south, Rte. 213 swings through cool woods and rolling hills, past farmhouses and fields of wheat and corn. As far back as the 17th century, English planters tended tobacco plantations here, using their profits to build gracious mansions and spending their leisure hours caring for their racehorses and hunting foxes.

Even today, racehorses are an ongoing “industry” in this part of Maryland. The 10,000-acre Maryland Lands Trust, one of the largest land preservation areas on the Eastern Shore, is home to a number of horse farms (as well as agricultural farms) and more than 1,000 of the nation’s most prized Thoroughbreds. They have included such equine luminaries as Kelso, Northern Dancer, Bet Twice, and other world-class equestrian champions.

The drive glides along Rte. 213 through Colonial villages such as Georgetown, Locust Grove, and Kennedyville, passing over tidal streams that feed the Chesapeake Bay to the west. Farther along, the entrance to Chestertown is signaled by a compound of brick edifices known as Washington College (named for the first president, who visited here in 1784 and donated 50 guineas towards its establishment). The handsome 18th-century village features sycamore-shaded streets, gardens trimmed with boxwood, and an inn more than two centuries old. Pre-Revolutionary houses built by well-to-do merchants face the Chester River, best viewed by walking across the Chester River Bridge. Down by the waterfront near the customs house, a historic moment took place in 1774 when townsfolk, disgusted with the British tax on tea, dumped a large shipment into the water. This patriotic act (reminiscent of the Boston Tea Party of 1773) is commemorated by residents each May with a Colonial-style parade.

3. Wye Mills
Traffic often crowds Rte. 213 as it nears the turnoff for the Chesapeake Bay Bridge, which links the Eastern Shore with Annapolis and Washington, D.C. After gliding by thickets of pine interspersed with wetlands, the drive crosses Rte. 50 and joins up with narrow Rte. 662.

Driving south, you’ll soon enter the crossroads of Wye Mills, where visitors can tour the 18th-century Wye Mill that lent the town its name. The mill once supplied cornmeal to George Washington’s hungry troops at Valley Forge during the frigid winter of 1778.

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