Only a few local historians and a small fan base are aware that the legendary Clara Bow was among the celebrities who spent time on the Eastern Shore long ago. But she did, in fact, own property on Taylors Island that she called “Happy Days,” where she threw infamously wild parties befitting her status as the Queen of Hollywood in the Roaring Twenties. Now, a modern legend, singer-songwriter Taylor Swift, has included a track titled “Clara Bow” on her 11th studio album, The Tortured Poets Department, and fans, critics, and scholars are trying to decipher the meaning of it.

In the song, Swift croons that she’s been compared to the movie star.

You look like Clara Bow

In this light, remarkable

All your life, did you know

You’d be picked like a rose?

But something more has inspired Swift here, and there are various theories. First, though, a little background on the subject is in order.

Clara Gordon Bow (1905-1965) competed in a nationwide acting contest in 1921. She was only 16, but she was “full of confidence, determination, and ambition,” reported Motion Picture Classic magazine, which added that she was “endowed with a mentality far beyond her years.”

This led Bow to the silver screen, and her performance in the movie It brought her international fame and the nickname “The It Girl.” She went on to appear in 46 silent films, including the first Best Picture Oscar winner, Wings (1927). Crowned the top box office draw in 1928, she also became the highest-paid movie actor at $35,000 per week. She was the #1 box office star again in 1929, the same year she made the transition to “talkies,” of which she made eleven.

At the peak of her stardom, Bow received over 45,000 fan letters in one month. Among her admirers were American gangster Al Capone and German Chancellor Adolf Hitler. Enthusiastic followers wore Clara Bow signature hats over Clara Bow hairstyles.

Fans also danced and smoked and partied like Bow, whose bohemian lifestyle was infamous. In the mid-20s, on her 300-acre Taylors Island property called “Happy Days,” she built a log cabin that was notorious for wild shindigs with bootleg liquor snuck onto the Eastern Shore during Prohibition. That property, 20 minutes southwest of Cambridge, is now Patriot Point, which is being developed as a retreat for wounded service members.

“My life in Hollywood contained plenty of uproar,” Bow said while reflecting on her career later. “I made a place for myself on the screen, and you can’t do that by being [Louisa May] Alcott’s idea of a Little Woman.”

She was always herself, brazen and confident in her sexuality, and perhaps that’s why so many men were drawn to her. These included actors Gary Cooper and Bela Lugosi, director Victor Fleming, and producer Howard Hughes, among others. Bow was engaged no fewer than six times, but she had trouble with commitment, complaining, “I really don’t care about men.” This all made her personal life endless fodder for the press, and wild rumors abounded, many of them untrue.

“Taylor Swift and Clara Bow have much in common,” wrote PBS.org’s Deirdre Clemente and Annie Delgado, “a meteoric rise to fame built on talent and hard work; a series of closely watched love affairs; and legal drama with managers, former friends, and the press. Both women redefined expectations of what an American woman could—and should—be.”

Bow’s great-granddaughter Nicole Sisneros described Bow and Swift to People magazine as “raw and amazingly talented artists.” And it’s obvious that the superstar singer has played up some of the parallels between her and the celluloid siren. There are photos of Swift styled much like portraits of Bow, and Taylor’s Schiaparelli look at the most recent Grammy Awards—complete with choker and pearl necklaces—echoed a similar ensemble of Bow’s.

But is there more to the song “Clara Bow” than these reflections?

Parade’s Jessica Sager called it an “ode to making it big and struggling with the trappings and pressures of fame and success.” And Stephanie Zacharek of Time said “the song is partly about self-possession and knowing the worth of your beauty, but perhaps even more about the worth others see in it—and their almost reflexive desire to market it.”

Equally as cynical is Bow biographer David Stenn, who supposed that Swift was inspired by the fact that the silent screen star “was both celebrated and condemned in the media in a way that male stars never were.” He added that “they build you up, and the only result of being built up is to be torn down.”

Swift obviously doesn’t want that last part for herself. She admits in the song:

I’m not trying to exaggerate

But I think I might die if it happened

Die if it happened to me

But Zacharek thinks the song “isn’t about Clara Bow the person at all, though it could be said to be about Clara Bow the vibe. Is it possible to be beautiful and charismatic to the point of possessing a kind of cosmic power that draws success to you?” Whatever the truth is, one can be certain that Clara Bow, once a regular in Dorchester County, has risen again in the 21st century, thanks to her admirer and successor, Taylor Swift.

Saturday, October 26, 1935, was clear and bright, with not much wind in Cambridge. Throughout the morning, many thousands of people from all over Maryland’s Eastern Shore and Delaware streamed into town until, by noon, there were hardly any available parking spaces left anywhere.

The recently completed dual road known as Sunburst Highway was decorated in flags and bunting from one end of the stretch to the other three-quarters of a mile away, where it connected with the Ocean City-Cambridge state road. An exciting holiday spirit was in the warm air.

The president was coming.

At 10:15 am, Franklin D. Roosevelt motored from Washington to Annapolis and boarded the USS Sequoia to travel down the Chesapeake Bay to Cambridge. He was accompanied by Secretary and Mrs. Henry Wallace, Mr. and Mrs. David Gray, and Miss Marguerite A. LeHand. The president was on his way to help dedicate the brand-new bridge across the Choptank River.

Built over a year and a half with funds from FDR’s New Deal agency, the Public Works Administration, and the State Roads Commission, this structure provided employment for more than 200 men from Dorchester and the surrounding counties during the dark days of the Great Depression. Hailed as a marvel of engineering and technology, it became the first connector at that place between Cambridge and Easton. Plus, the two-mile span made it the longest bridge in all of Maryland.

It marked the fruition of a dream visualized by Senator George L. Radcliffe, a local boy.

The master of ceremonies, Governor Harry W. Nice, made the trip to Cambridge on the steamer duPont, flagship of the Maryland Conservation Department, which had been presented to the state by Mrs. T. Coleman duPont, widow of US Senator duPont of Delaware. The governor’s party included Mrs. Nice, Mr. and Mrs. George Clayton, Mr. and Mrs. Thomas Ewalt, Mr. and Mrs. Frank Pearson of Baltimore, Mr. and Mrs. Chester Cloud of New York, and Miss May Nice of Annapolis.

Greeting FDR in Cambridge

The bridge was attired in festoonings at both entrances and on the four truss spans that were supported by the piers. Twenty-five Maryland State Police officers were on hand, and members of the National Guard, Boy Scouts, and Rescue Fire Company were sworn in as special police for the occasion.

Delegations from Dorchester and Talbot Counties gathered at the draw of the bridge for the dedication. Also present were the governors of Delaware, Virginia, Pennsylvania, and New Jersey, as well as three former Maryland governors–Albert Ritchie, Phillips Lee Goldsborough, and Emerson C. Harrington.

Gov. Nice told the cheering spectators that the bridge had cost $1,409,273, partly covered by a grant of $506,373.43 from the PWA. He admitted it hadn’t been easy to convince the public of “the economic benefits of linking Cambridge with the county to the north.” Nice announced that the bridge was being named for Harrington, the World War I-era governor and a native of Cambridge, who accepted it with the comment, “I hope it will be merited.”

Former Maryland Governor Harrington

At 2:30 pm, Roosevelt made his appearance. While the turntable span opened, the Sequoia waited nearby and then became the first vessel to pass through. The boat turned around upstream of the bridge and steamed through again, with the president waving to the crowd that lined the shore. Naval planes from Annapolis maneuvered above and after the draw was closed.

Then, the ribbons were cut on both the Talbot and Dorchester sides, officially opening the Emerson C. Harrington Bridge to traffic, which began immediately. The dedicatory procession started across toward Cambridge, accompanied by the music of the Rescue Fire Company band and the Drum and Bugle Corps of American Legion Post Number 9.

The Sequoia pulled up to the dock at Long Wharf, where a number of old warehouses had been torn down at the Secret Service’s request. The crowd gave Roosevelt “a tumultuous welcome.” He did not disembark, as that would have revealed he needed a wheelchair to get around, but he stood at the railing and made a brief congratulatory address that was broadcast over a national hook-up.

“Governor Nice, my friends,” said FDR, “I didn’t come here to make a speech but to take part in a little ceremony largely because of my friendship for a neighbor of yours, George Radcliffe. About 15 years ago, when I first was associated in business with him, he began talking to me about the need for a bridge at Cambridge. When I went to Washington and helped in building, I was very happy.”

The crowd applauded heartily, and the Sequoia headed back up the Chesapeake to the Potomac River.

That evening, a banquet was held for 500 people at the state armory in Cambridge, arranged by W. Enos Valliant of the Cambridge-Dorchester County Chamber of Commerce. It was followed by a dance that lasted until midnight. The program concluded with a massive fireworks display.

Author David Williams

The Chesapeake Bay has a long and storied history of sailing, fishing, and shipping, but not all the activities on those waters has been noble or even legal. On March 6, the South Dorchester Folk Museum hosted David Williams to present a talk on “Pirates, Privateers, and Smugglers of the Chesapeake” at the Robbins Heritage Center.

Williams, a retired Ford Motor Company employee and current Nathan of Dorchester captain, dressed in colonial garb, carried an aluminum sword, and called himself “Captain Graybeard.” While he obviously was enthusiastic about his subject matter, it was not a very exciting talk, as the “captain” mostly read off a power point presentation. But, there was quite a bit of information that would interest Eastern Shore residents and pirate buffs.

Pirates and Privateers

All through world history, there have been those who robbed people of their transported goods at sea. These pirates—also called buccaneers, freebooters, corsairs, and other names—generally focused on ships, although some made attacks on coastal settlements. Many thousands of pirates operated during the “Golden Age” of piracy between 1650 and 1720, among whom were Henry Morgan, Edward “Blackbeard” Teach, and William Kidd, the last one even spending some time on the Chesapeake Bay. Another whose activities brought him to these waters was Bartholomew “Black Bart” Roberts, also known as The Crimson Pirate.

But some of those mentioned wouldn’t have considered themselves pirates, but rather privateers. While a pirate was an independent “businessperson,” a privateer sailed with a “letter of marque” from his government authorizing him to steal from the vessels of other countries. This was a low-cost method for a government to increase the size of its navy, and the privateers were required to share their spoils with the authorizing body, so it was lucrative as well.

Privateers were considered a bit more “respectable” than pirates, but the truth is that one person’s privateer was the opposing person’s pirate, especially since the privateer’s actions tended to be rather piratical. In fact, many privateers came to ignore the distinctions between nations when attacking ships or towns.

William Claiborne and the Maryland-Virginia Conflict

In 1627, Virginia Secretary of State William Claiborne “discovered” an island in the Chesapeake Bay and named it Kent Island after his English hometown. Recognizing its strategic importance as a trading center, he established a settlement on the island in August 1631. At this time, the colony of Virginia extended to the northernmost part of the Chesapeake. When the king of England granted Cecilius Calvert, Lord Baltimore, the territory to be called Maryland after Queen Henrietta Marie, it became apparent that there was a boundary overlap with Virginia. 

Protests were raised, but they fell on deaf royal ears. However, when the ships the Ark and the Dove landed at St. Mary’s in February 1634, the new colonists kindly told Claiborne he could keep his trading post…so long as he conceded Kent Island belonged to Maryland. He apparently wasn’t happy with that arrangement, but he protested in his own way. 

In the spring of 1635, one of Claiborne’s ships, the Long Tayle, attacked a small Maryland trading pinnace near Havre de Grace. The seizure of that pinnace was to be the first documented act of “pyracie” on the Chesapeake Bay. Battles commenced, people died, and ships were taken on both sides. Two of Claiborne’s men were convicted of piracy but then pardoned. Claiborne himself was sent back to England to face charges of piracy. His property was given to Lord Baltimore, who then controlled Kent and Palmer Islands.

Privateers of the Revolution

When the American Revolution began, Britain had the most powerful sailing fleet in the world. The colonial forces, however, had none at all. Without the ability to impose taxes to raise war funds, the Continental Congress had to get creative in order to develop its own navy. So, it issued letters of marque to create privateers among the patriots. And men like Robert Morris of Oxford, Maryland, provided ships for the purpose.

Colonial privateers formed a fleet of more than 2,000 vessels with 18,000 cannons and 70,000 men. They acquired $50 million for the owners and supported George Washington’s army. In fact, Morris became wealthy and was able to help finance the Revolution.

When Virginia and Maryland’s royal governors abandoned their offices and fled to the protection of British warships, the colonials took over the governments. Because only a third of the colonists supported the rebellion, the new governors were forced to impose taxes and restrictions on the citizens that were just as harsh as those of the British.

This did not sit well with the free-spirited residents of the isolated Eastern Shore, many of whom became British privateers. The most infamous of them was Joseph Wheland, commander of Britain’s privateers in the Chesapeake. He and his men wreaked broad havoc, especially on the Eastern Shore, disrupting shipping and raiding plantations. Because the Shore was producing vital foodstuffs for the Revolutionary army, Wheland made a point of destroying the food as well as homes, farms, and means of production.

When a detachment of colonial Major Fallin learned that Wheland was in the Hooper’s Strait area, they seized his ship and cargo of iron, guns, swords, and ammunition. He and his men faced many charges, and Wheland himself was ultimately convicted of piracy and having loyalist sympathies. Jailed in Frederick County until he could offer restitution to John White for the burning of his sloop, Wheland was released in 1781.

Smuggling on the Bay

In order to raise money from its colonies, Britain imposed import duties, which strangled commerce and dampened trade and competition. So, many colonists chose to circumvent the laws. Britain labeled colonial smugglers as pirates, who could be taken to London, tried, and inevitably executed. Those on land who helped the smugglers faced the same fate. The colonists were not to be cowed, but they did have stiff competition in the form of the East India Company, which was the only official importer of tea to the colonies in the early 1770s. Because the cost of tea was reduced, the smugglers protested by arranging the Boston Tea Party and the Chestertown Tea Party.

Civil War increased the opportunities for smuggling on the Eastern Shore. Many of its residents were sympathetic to the Confederacy, and they smuggled various goods through the federal blockade to the South. There was also smuggling on the other side of the conflict—human smuggling—as the Underground Railroad helped runaway slaves escape north.

Passage of the 18th Amendment to the Constitution in 1920 brought about Prohibition, which outlawed the manufacture, transport, and sale of alcohol. This gave rise to the smuggling of liquor from home breweries, stills, and abroad. This illicit manufacturing thrived on the remote Eastern Shore, where many of the inhabitants were involved in the business.

The Chesapeake Bay was the perfect place for “rum running,” thanks to its miles of shoreline, rivers, and inlets. The Coast Guard, who was chiefly responsible for stopping smugglers there, found it impossible to properly police 11,684 miles of coastline. While large liquor-bearing boats from overseas waited past the three-mile limit, small craft pulled alongside at night or when the Coast Guard boats were elsewhere, loaded up, and snuck back into the Bay. Then they would travel to a drop-off point to meet a car or truck that would whisk the booze off to the cities.

The fastest rum-running boats were the 53-foot-long Whippoorwill and the 56-foot Hiawatha. With its three 450-horsepower motors, the Whippoorwill could not be caught. But, in May 1931, federal and county officials ran a sting operation at Taylor’s Island, which had been a rum-running base for more than a year and had a radio operator for giving directions to the smuggler boats. The Whippoorwill and Hiawatha were caught, netting the government 14 prisoners, a fleet of trucks, and 6,000 cases of liquor.

Conclusion

While piracy still exists in the world, it has pretty much disappeared from the Chesapeake Bay, where it is no longer in demand. But the memories remain, in oral and written form, and occasionally they’re brought out by folks like David “Captain Graybeard” Williams to be experienced once again.