Five Fun Historical Things to Know About Chesapeake Bay Beaches

You think the lines across the Chesapeake Bay Bridge are long and slow now? Before the bridge opened in 1952, cars were taken across from Annapolis to Matapeake on the Eastern Shore by ferry.

Chesapeake Bay ferry
Chesapeake Bay ferry (Photo courtesy Chesapeake Bay Maritime Museum)

As Washingtonian magazine reports, it took 40 minutes and the line of cars waiting for the ferry stretched three miles. Actually, the Bay Bridge backup on the eastbound side now stretches to ten miles, but it take five minutes to cross the bridge by car. But if you still want to experience a car ferry, there’s one that goes across the Tred Avon river at Oxford.

Oxford-Bellevue Ferry in Maryland
Oxford-Bellevue Ferry is America’s oldest privately owned ferry, established 1683. It crosses the scenic Tred Avon River between Oxford and St. Michaels area.

Those original ferries also made stops at summer resort towns with huge hotels, ferris wheels, carnivals and boardwalks for Victorian America. 

One of the most famous was Tolchester Beach near Rock Hall on the Eastern Shore, drawing visitors by boat from Baltimore and Annapolis.

One of the more interesting tidbits about Tolchester is that they would rent bathing suits. In 1887, the resort had 500 suits for rent. By 1909, they were renting more than 2,000.

“The one-piece men’s knit suit stretched from the neck to mid-calf; the women’s suit included a blouse with skirted bloomers which covered the body from the neck to the knee and shoulder to wrist,” writes Maryland Online Encyclopedia. “The outfit was completed with black stockings.”

Betterton Beach, MD
Betterton Beach “Jewel of the Chesapeake” before the Bay Bridge was built (photo courtesy Town of Betterton)

Railroads came through the Bay area in the early 1900s and that’s when the largest, Chesapeake Beach, was built. Chesapeake Beach is still there, but it’s not the resort is used to be. The others died out when the Bay Bridge was completed and motorists started going to  Delaware’s and Maryland’s East Coast beaches. Tolchester Beach is now a marina. The picture of Tolchester now is at the top of this story.

North Beach, MD
North Beach, Maryland. The closest to a Victorian beach on the Chesapeake Bay.

Actress Tallulah Bankhead, whose career spanned the 1930s through 1950s, is buried near Chestertown. 

Her sister lived near Rock Hall and wanted Tallulah nearby after she died at age 66 in 1968.

Tallulah Bankhead
Tallulah Bankhead (photo courtesy Alchetron.com)

Okay, that’s not really a beach story, but it’s still kinda cool to know.

Back in the 1950s and 1960s, beaches around the Chesapeake Bay were still segregated and one of the hottest beaches for African Americans was Carr’s Beach in Annapolis.

Saturday nights grown-ups would go to the  beach and see stars such as Ray Charles, Bill Doggett, Dinah Washington, Author Prysock, etc.  Sunday afternoons was family fun. Thousands of people from as far away as Philly  would come to the beach to swim and picnic. But at three o’clock  it was show time and people would pack into the pavilion to see and dance to the Major R&B stars of the day. Stars such as Little Richard, James Brown, Lloyd Price, Etta James, The Shirelles, The Coasters, The Drifters. You name ’em, they played Carr’s Beach. – Carr’s Beach.com

Nearby Highland Beach was founded by Frederick Douglass’s son Charles and daughter-in law, Laura, in 1893 after they were refused service at a restaurant in another beach community in Annapolis. Both resort beaches are long gone. Carr Beach is now a waterfront condo community. Highland Beach is a community of about 60 homes.

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