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This is an excerpt from my book, Eastern Shore Road Trips 2: 26 MORE One-Day Adventures on Delmarva. It’s a sort of historical endnote to a chapter where I get off the highway and wander around Kent Island, Md, learning about the stories the place has to tell and the sites (and sights) it has to see.

History is a funny thing. Once a big event is in the books, everything about the way it unfolded starts to look inevitable, like it was bound to happen in just the way it did. So it is with the Chesapeake Bay Bridge, which opened on July 30, 1952.

But sometimes it’s fun to play a little what-if. For instance: What if one or another of the various other Bridge plans put forward over the years had been realized instead? What would the Shore look like today?

1907: The Trolley Crossing

The earliest plan for a Bay crossing dates to 1907. At the time, business leaders in Baltimore were nervous, as railroad lines had begun making it easier and cheaper for Eastern Shore goods to get to Wilmington and Philadelphia.

Worried that Baltimore would lose out, the business community there got behind a proposal by State Senator Peter C. Campbell to build an electric trolley line between Baltimore and Chestertown. They soon hired the engineering firm Westinghouse, Church, Kerr & Co, Inc., which delivered a plan that not only had the trolley crossing the Bay but also envisioned a 235-mile network of new trolley tracks connecting all of the major towns on the Shore.

The price tag on the Trolley Plan came in at $13 million, and that number seems to have scared everyone off.

1918: The Double Decker

At the end of World War I Gov. Emerson C. Harrington got behind a plan to build a double-deck bridge linking Bay Shore and Tolchester, on the Upper Shore in Kent County. One deck would be for freight trains, and the second deck would be for passenger trolleys. The plan lost out to a new and expanded ferry service, including between Annapolis and Claiborne. Later, a Kent Island ferry landing would be moved to Matapeake, and the Annapolis landing would be moved to Sandy Point.

1929: The Tolchester Crossing

This is the one that came closest to actually happening. Both the Maryland legislature and the U.S. Congress signed off on the plan to build a bridge from the Baltimore suburb of Edgemere, near Hart-Miller Island, to Tolchester Beach. The politicians even went so far as to appropriate $500,000 to get the show on the road—then the stock market crashed.

1930s: Try, Try Again

Various bridge plans came and went during the 1930s. The reports I’ve read all say that these plans fell by the wayside because no federal funding ever materialized. The year 1937 seems to have been the first time that a crossing from Sandy Point to Kent Island entered the mix. That plan was still on the table when World War II broke out and scuttled all bridge discussions for a while.

1949: The Chesapeake Bay Bridge We Know

Gubernatorial candidate William Preston Lane campaigned on a promise to get the Chesapeake Bay Bridge built at last, and the project was dubbed “Lane’s Folly” by his opponents. Here are a couple of choice quotes from people who thought the bridge was a really dumb idea.

• State legislator Henry Balch from Talbot County: “The proposal to build the Bay Bridge is extravagance to the nth power. The spending necessary would exceed the aggregate spending of every drunken sailor since John Paul Jones.”

Baltimore Sun columnist (and so-called “Sage of Baltimore”) H.L. Mencken: “There is not the slightest reason to believe that any such structure could ever earn enough to pay the interest and amortization. … There is simply not traffic enough between the Eastern and Western Shores, and there is no evidence that there will ever be enough hereafter.”

But once he became governor, Lane proved the doubters wrong. The first shovel went into the ground in November 1949. Three years later, ex-Governor Lane was a guest of honor in the first motorcade across the Chesapeake Bay Bridge that we know today. Between all the sightseeing and backslapping along the way, that motorcade took more than two hours to make the crossing, so that first ride across the span qualifies as the very first Chesapeake Bay Bridge traffic jam, too.

–written by Jim Duffy and excerpted from Eastern Shore Road Trips #2: 26 MORE One-Day Adventures on Delmarva. Copyright Secrets of the Eastern Shore/Whimbrel Creations, LLC. Find out where to buy that book in area stores and online here.

NOTE: Most of the material here comes from research I did for a 2002 article in the now-defunct Chesapeake Life Magazine. Alas, it’s not online anywhere–I went back to the hard copy here.

LAST BUT NOT LEAST: Below here is an incredible photo of an iconic moment–the opening-day motorcade coming east across the Chesapeake Bay Bridge while a soon-to-be-shut-down steamboat crosses to the west in the bridge’s shadow.

Opening Day Traffic on Chesapeake Bay Bridge with Ferry


  • Share says:

    Great info! Thank you! We live and love the Eastern Shore! Always enjoy hearing about it ♡

  • Donald Shores says:

    My grandfather and great grandfather were both supers for Wagman and Whiting-Turner. My grandfather worked on the new span, my great grandfather on the original. Being raised on Kent Island by my grandparents, I still remember back in the 80’s/90’s my Pop coming home at ungodly hours from his overnight shift doing repairs and whatnot on the newer span. He also did work on the Harry Nice Bridge, the Key Bridge, as well as many of the overpasses and interstate junctions around the region. A knee injury put him out of work in the 90’s, but man did he have some cool stories to tell. As well as a couple photo albums with some pretty interesting photos. Definitely a great symbol of pride to me knowing my family had a hand in building something that today is so important to so many people. Great article! Thanks for sharing!

    • Michael says:

      You should donate or make a book with all of these photos. I am sure that Kent island residents as well as the heritage society would love to see them

  • SHEILA NIMM says:

    All good and well in my lifetime, but, the growth is so great, the congestion so dramatic the time has come for a southern crossing from Calvert or St Marys to Dorchester. It is iresponsible to entice people to the beaches and provide miles of misery in the process..

  • Susan Gray says:

    My grandfather, Royden S. Meise, was in that motorcade – he rode across with the governor. Little did they know what the bridge did for tourism!

  • Jeanie Coolahan says:

    Very interesting information; enjoyed the article; I love reading anything to do with the Eastern Shore….it’s like having heaven on earth on the Shore!

  • Liz Parker says:

    Can anyone identify the ferry boat that is running in the photo of the bridge? Looks like the John M. Dennis to me, but not certain.
    If it is, would love to purchase a copy of the photo. My grandfather, and a couple of uncles were the Captains that run that boat.
    Many thanks.

  • Larry Erdman says:

    When I was a kid in the late 50’s we vacationed over at Dewey Beach, DE. When we traveled back and forth there were rockets on launchers where Whitehall Inn later stood. Does anyone know the story of them? Why were they there? Put up removed?

  • Nelda Thomas says:

    Nelda Thomas I remember taking the Ferry across before the bridge to go to Ocean City about 1950. It was so exciting when they built the bridge and we did not have to sit in the lines for the Ferry.

  • Ron says:

    I was born in 1948. I do not remember taking the ferry, but I do remember waiting for it. Everyone got out of the cars and sat by the side of the road. I do remember my first trip across the new Bay Bridge on our way to OC shortly after it opened. My Dad worked on the construction of the second bridge. He worked the second shift. He boarded a crew boat and got off at the huge concrete bulkheads. He constructed wooden forms for each days concrete pour.

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