Five Famous Road Trips

If coverage of the Historic Vehicle Association’s “Road Trip Century Celebration Tour” isn’t enough to get you excited about hitting the open road with friends, history offers plenty more inspiration. Imagine tagging along on one of these “epic” road adventures.

The 1919 Transcontinental Convoy



Imagine traveling 3,200 miles across the continent with a bunch of cool trucks and motorcycles, sleeping under the stars with 300 of your best buddies and a future sitting president—all with the monetary backing and logistic support of the U.S. military.

Nobody was shooting at the men and machinery traveling from Washington, D.C. to San Francisco as part of the U.S. Army Transcontinental Motor Convoy, but in 1919 the cross-country trek was far from easy. West of the Mississippi the road system varied from poor to nonexistent, so driving from sea-to-shining-sea meant going by railroad or—as the mission would prove—driving at a speed just slightly faster than a person could walk.

Dwight Eisenhower, then an army Lieutenant Colonel, volunteered for what became an arduous, two-month expedition plagued by constant breakdowns and accidents. Traveling at a snail’s pace—and often being forced to push machinery along a tangle of dirt roads, rutted paths and winding mountain trails—the men of the Transcontinental Motor Convoy proved what ranking members of U.S. Military suspected: The country was in big trouble should a foreign invader ever set foot on American shores.

But it wasn’t all mud and backbreaking drudgery. According to records at the Library of Congress, Eisenhower and the boys managed to have some fun. Along with his friend Major Sereno Brett, Eisenhower played numerous practical jokes on junior officers, “including staging a phony western shooting and a fake knife fight.” He never forgot the experience and, as president, urged Congress in 1956 to create the Interstate highway system as a national priority with 90-percent of the funding coming from the federal government.

On The Road With Harry and Bess Truman



Freshly out of a job in the summer of 1953, Harry Truman and his wife, Bess, piled into the front seat of a big, black Chrysler New Yorker and left Independence, Missouri, on a three-week road trip to New York.

With only a small army pension and no secret service protection, the former first couple stopped at roadside diners, pumped their own gas and were even pulled over by Pennsylvania State Trooper for driving too slow.

Author Matthew Algeo chronicled this amazing, amusing tale in his 2009 book, Harry Truman’s Excellent Adventure: The True Story of a Great American Road Trip. According to an op-ed he penned for the New York Times that same year, Angeo wrote that the trip—unfathomable in this era of 24-hour-news—was simply Truman’s effort to make the transition from leader of the free world to, as the ex-president put it, a “plain, private citizen.”

The Cruise of Rolling Junk



Every fan of great literature knows the way the story ended for F. Scott Fitzgerald and his notoriously wacky wife, Zelda. Fitzgerald—or “Scott” as his pal Ernest Hemingway used to call him—was a sickly alcoholic and one of the greatest writers of twentieth century. Zelda battled a mental disorder that eventually caught up with her.

Together, the two of them were known for their wild New York parties, bitter fights and public drunkenness. But in the summer of 1920, the party was just beginning for the newly married Fitzgeralds after the publication of Scott’s first novel, This Side of Paradise. The author’s greatest-known work, The Great Gatsby, was still five years away when Zelda experienced a sudden homesickness for the taste of Alabama biscuits and peaches. The two decided to leave Connecticut in their unreliable, secondhand Marmon, embarking on a 1,200-mile road trip in which everything that could go wrong did.

Plagued by chronic breakdowns, convoluted guidebooks, condescending mechanics, misleading signs, and foul weather, the calamitous trip was later chronicled by Fitzgerald in a series of articles for an American magazine, Motor. These articles were later rediscovered and compiled into the humorously titled book, The Cruise of Rolling Junk, in 2012 by the U.K. publisher, Hesperus Press.

Travels with Charley



Unlike the Fitzgeralds, whose cross-country trek was inspired by total whimsy, the famous road trip taken in 1960 by John Steinbeck and his dog—a 10-year-old standard poodle named Charley—supposedly had a more serious purpose.

At 58, the Pulitzer-Prize winning author best known for The Grapes of Wrath and Of Mice and Men wrote that he was moved by a feeling that he had lost touch with America after years living in New York and Europe.

Compelled to reconnect with the country and the people he spent his career writing about, Steinbeck and his dog drove some 10,000 miles in his looping quest from New York to North Dakota, California to Texas, before returning home. The resulting book, Travels with Charley, became a New York Times bestseller (for one week, anyway).

Steinbeck undertook his journey in a most un-writerly vehicle—a three-quarter ton, GMC V-6 pickup with a camper mounted on the bed that he christened Rocinante, after Don Quixote’s horse. Many American writers have gone looking for the “heart of America” on the open road and been somewhat disappointed by what they found. On Steinbeck’s journey he saw troubling trends brewing in the country: namely, according to the Steinbeck historian Bill Bariach, “the death of localism, the growing homogeneity of America and the trashing of the environment.” Perhaps more interesting, however, is what was later revealed by Steinbeck’s oldest son—that the real reason for his father’s trip was that the author had a heart condition, knew he was dying and just wanted to see America one last time.

Willie Nelson


On The Road Again

Here’s a hypothetical question to ponder with some of your music-loving friends: If you could have tagged along on a cross-country concert tour with any famous musician from the last 50 years, who would it be? Regardless of your taste in music, you’d be hard pressed to share a ride with a more legendary personality than Willie Nelson.

Back in 2012, music fans collectively inhaled when news broke that “Honeysuckle Rose”—one of Willie Nelson’s iconic tour buses — was headed to the auction block with an asking price upwards of $60K to $80K. Auction advertising billed the 40-foot, 1986 Eagle 1 Motor Coach as Willie’s home on the road during his “Highwaymen” years and the scores of shows he played while crisscrossing Canada and the U.S. with fellow music legends Waylon Jennings, Kris Kristofferson and Johnny Cash.

Unfortunately, the bus bombed at auction when it was uncovered that the tour bus was actually owned by a band member in Willie’s entourage and not the “Red Headed Stranger” himself. While nobody argued that this bus wasn’t a part of the tour—which, for a country music fan, makes it just about priceless when it comes to the memories it must have helped make—when the smoke lifted (as it were), hammer price was a mere $29K.

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