The Chesapeake Bay’s Eastern Shore is a special place; a place alive with stories.

An expanded view of the  Eastern Shore would include all of what’s called the Delmarva — Delaware, Maryland, and Virginia — Peninsula and would encompass everything from the eastern foot of the Bay Bridge to the Atlantic Ocean and from the lighthouse at Cape Charles north to the Chesapeake’s upper tributaries, but as with any special place, the gateway often holds much of that place’s power.

Image result for delmarvaCourtesy Delaware Public Archives

Kent Island, the largest island in the Chesapeake Bay, and one of the oldest permanent English settlements in our country, originally claimed for the Virginia by the surveyor/ fur trader William Claiborne in 1631, and predated only by Jamestown and Plymouth, Massachusetts, is the first stop upon arrival in the Land of Pleasant Living.

William Claiborne 2Courtesy Encyclopedia Virginia

Claiborne built the upper bay’s first trading post, fort, and English residences. Kent Island’s Christ Church Parrish is Maryland‘s oldest active religious congregation.  It is said the first boat built entirely of wood indigenous to the Chesapeake Bay, The Long Tayle, was built in Claiborne’s shipyard.

Years of violence, bad blood, and the first recorded naval battles and charges of piracy  in North American waters followed after King Charles I granted to George Calvert, the original Baron of Baltimore, a charter for the colony of Maryland, which included the Eastern Shore and Claiborne’s already settled “Isle of Kent”.

Claiborne, though on the losing end of history, did not give up easily. Feeling wrongly persecuted and badly treated, he argued and battled tenaciously, and long after defeat, bad-mouthed his enemies and harbored bitter resentments.

On the Eastern Shore, we know how to hold a grudge.


For generations, except for certain advancements in work or leisure, life on the Eastern Shore remained virtually unchanged; small agricultural communities and hardscrabble watermen’s enclaves populated by independent and stubborn hard-working people known for the blunt earthiness and salty eccentricity that comes natural to tough folk living off the land and the water. Early in the morning, the Chesapeake Bay always belonged to the watermen, and the land to the farmers.

The first span of the William Preston Lane Jr Memorial Bridge, the Bay Bridge to everybody except the state of Maryland, opened in 1952. Before that, access to and from  the western shore (the Eastern Shore is always capitalized, the western shore never) was feasible only by boat – dugout log canoes and sailing ships, barges and bugeyes, schooners and skipjacks, steamers and ferries.

Though generally self-sufficient, life on the Eastern Shore in the decades before the bridge had required interaction with the outside world: supplies, mail, news, and even entertainment (as evidenced by the early 20th century’s James Adams Floating Theater), were shipped in; seafood, farm products, (and the occasional prodigal son or daughter who was “Craving the World”), shipped out.

The Bay Bridge changed all that.


20451622_700013160196335_1850625653220871594_o (1)Courtesy Kent island Heritage Society

Much of the Eastern Shore can still be called rural-in-nature, but suburban sprawl has increased exponentially in recent years, and the gateway areas within 20 miles of the bridge have been perhaps the most transformed.

east fromcox crk80

Though there’s always been some reluctance to accept “foreigners” – anybody whose family tree doesn’t have roots going back seven generations – one attribute we on the Eastern Shore have always been known for is our hospitality.

Colonial era ordinaries and taverns were at the heart of regional economic, political and social activity, serving villagers and travelers alike. The tavern proprietor also often functioned as postmaster, real estate agent, auctioneer, arbitrator, and referee.

After the Civil War, as our economy expanded, boardinghouses and hotels began to proliferate. Around the turn of the 20th century, and for 50 years or so, our Chesapeake shorelines were dotted with grand vacation resorts such as Kent Island’s Love Point Hotel, where in the early 1930s, a buck and quarter bought you an-all you-could-eat meal of crabcakes, softcrabs, fish and oysters, Maryland fried chicken, chops, steaks, corn-on-the-cob, mashed potatoes smothered in country butter, local tomatoes, hot beaten biscuits, and homemade pies and cakes.

And of course there was nothing like a little sweet tea, or local bootlegged liquor, to wash it all down.5253Courtesy Kent island Heritage Society

The Eastern Shore, like most places with a long history, also has its share of legend and lore that is scoffed at in the light of day, but isn’t as funny after the sun goes down.

In the old days, folk feared will-o’-the-wisps or jack-o’-lanterns, mysterious lights that appeared at night, hovering over the salt marshes at a distance, and luring susceptible victims to a watery grave.

Ghosts abound.

In 1712, an Eastern Shore spinster named Virtue Viol was prosecuted in Maryland’s last witch trial.

Over several frantic nights in July 1952, just as the Bay Bridge was opening, a commotion of UFO activity was documented from the lower Eastern Shore to the seats of power in Washington, D.C.


Certainly the most celebrated mystery in the modern era is reports of a strange 30-40 foot bay serpent, affectionately called Chessie.

There is still an occasional sighting, but the Chessie frenzy was concentrated in the waters surrounding Kent Island throughout the 1980s, and garnered national attention after a local family supposedly videotaped the cryptozoological creature.

Though skeptics speculate what witnesses have actually seen is such natural phenomenon as detached construction equipment or displaced marine animals, others believe Chessie could be anything from a surviving prehistoric monster to a giant mutant eel.

Sometimes gateways can be mysterious places.

Chessie,_A_Chesapeake_Bay_Story_Cover_ArtCourtesy Britt Eckardt Slattery – Environmental Protection Agency, Public Domain,  

Books by Brent Lewis are available on

Remembering Kent Island: Stories from the Chesapeake and A History of the Kent Island Volunteer Fire Department published by Arcadia Publishing & The History Press:


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