Best Road-Trip Books and Music To Go

Stories about road trips come in many flavors these days but mainly in abundance and closely tied to advertisers. I like mine kind of weird because road trips are memorable for the things that go wrong, the mates, the misfits, the quirky connections, and the music more than the meals and monuments.

These are some I read, watch, and listen to again and again.

“Blue Highways” by William Least Heat Moon. Cross country travels (including Tennessee) on backroads colored in blue in printed maps. Good one, but I like his “River Horse”— America coast to coast by small boat better because I know more of the places on the Ohio, Mississippi, and Missouri rivers. Mr. Least Heat Moon has a thing for last names, beers, boats, and big words that I have to look up so I can use them too.

Roads; Driving America’s Great Highways, by Larry McMurtry. This short book (206 pages) is about interstate highways. He drives solo, so it’s kind of like being the passenger that he doesn’t really want to talk to. But he’s the author of “Lonesome Dove” so I have dogeared several pages anyway.

On the Road, by Jack Kerouac. In my three score and ten I have read or put down this book many times. It is overpraised as a “classic” of the Beat Generation and overcriticzed as unedited “typing” by Truman Capote. Kerouac and his buddy Neal Cassady (Dean Moriarty in the book) were ruggedly handsome dopers who, some say, had a thing for each other.

“The Electric Kool-Aid Acid Test” by Tom Wolfe. Ken Kesey, Neal Cassady, Mountain Girl, and the Merry Pranksters take a druggie bus trip across the country, as told by the greatest of the New Journalists of the Sixties.

“Travels With Charley” by John Steinbeck. A hugely popular prize-winning non fiction book about the novelist’s 10,000-mile road trip in a camper with his dog. Full of the detail and fine writing by the author of “The Grapes of Wrath”. Also some improbable stretchers, as noted by journalist Bill Steigerwald who retraced the route 45 years later in his less popular book “Dogging Steinbeck”. Both books are a delight. But they show the perils of a solo road trip: boredom, fatigue, and a desire to get home.

“The Road” by Cormac McCarthy. No cars. Post-apocalyptic hike by father and son from (probably) Knoxville (McCarthy’s home) to the sea (Florida). Encounters with murderous cannibals and worse, but they make it and dying dad says “You’re the best guy” to the kid. Weird tearjerker.

“The Negro Motorist Green Book” was a travel handbook published annually from 1936 to 1966 as a guide to the South. It was made into a comedy/tragedy movie in 2018.

“The Lincoln Highway: Main Street Across America,” by Drake Hokanson. A Ford Model T was the choice of Henry Ford in 1914 when he persuaded Thomas Edison, Harvey Firestone and naturalist John Burroughs (The Four Vagabonds) to join him on a road trip. Every good road trip needs a buddy. Edison, like Ford, was an inveterate tinkerer. Firestone had a vested interest because cars needed rubber tires, which Firestone would produce in Akron, Ohio and, later, in Memphis. But he thought roads should be funded by private donations instead of government. Burroughs was a bearded tree-hugger who thought the automobile would end life on this planet. Ford took a shine to him anyway.

“Out of that automobile grew a friendship,” Ford wrote in his memoirs. Out of that friendship grew a country. And — a century later — a neologism: “glamping.” The Vagabonds had a caravan of cooks, cops, and camping equipment behind them to keep them going in style.

Footnote: Harvey Firestone’s son Raymond lived in Memphis on Central Avenue near Memphis Country Club. Firestone was a major sponsor of pro golf tournaments in Memphis in the Thirties and Forties and in Akron until 2026. The tire factory in North Memphis closed and was demolished in 1983. You can still see the smokestacks.

“The Fifties” by David Halberstam for chapters on Memphians Kemmons Wilson and Sam Phillips. “The vacation that changed the face of the American road occured in the summer of 1951.” Wilson loaded his wife and five children into his Oldsmobile for a road trip. Motels were dicey and charged extra for children. Wilson was thrifty and knew how to build houses and bedrooms. And where to build his Holiday Inns from flying around in a private plane with Memphis newspaper reporter Bill Burk and scoping roads and intersections. Phillips was “a redneck” from north Alabama who drove his Cadillac 100 miles west to Memphis to found Sun Studio and discover Elvis — “a white boy who could sing like a Black man.” Both became famous for driving and giving away new Cadillacs with bold colors and tail fins.

Which leads me to the connection of cars, radios, and music to road trips. Dinah Shore from Nashville was a singer who ended her show with a hearty chorus of “See the USA in your Chevrolet.” So we did. Millions of us. On family road trips. Cool kids, though, cruised to the coasts in a Corvette convertible to the big-band sound of Nelson Riddle’s Orchestra playing “Route 66”. A 1960 Corvette convertible was the Marilyn Monroe of American sports cars.

James Taylor wrote so many songs about the road, the highway, and leaving that he began to parody himself. Junior Brown’s “Highway Patrol” will keep you awake better than coffee, Dave Dudley’s “Six Days on the Road” is top trucker stuff, Asleep At the Wheel is welcome any time, Donald Fagan’s “Kamakiriad” is a futuristic road trip about the Florida room, the dunes, the sea, tomorrow’s girls and the teahouse by the tracks. Nat King Cole’s version of “Route 66” can put you to sleep.