Bad Boys of Books Interactive National Road Trip Map

© Author Adventures

The Bad Boys of Books National Road Trip, an example of a trail organized by theme, is a tongue-in-cheek tribute to the guys with gusto, writers whose fearlessness won hearts and earned respect.

These writers attracted attention and gained success by expertly challenging what was popular. The more we understand the twists and turns of their lives, the more we can appreciate their work and the lessons taught through their words and example.

The Bad Boys Road Trip begins in Massachusetts, takes you south to Key West, westward to Los Angeles and continues on to circle the nation, ending in Maine.

Starting in the Northeast:

1. Jack Kerouac – Massachusetts The original hipster known as the literary lion of the counter-culture Beat generation.

2. Henry David Thoreau – Massachusetts The author of Civil Disobedience was imprisoned for refusing to pay his taxes.

3. Mark Twain – Connecticut His clever wit and edgy perspective changed the way generations of readers thought.

4. Washington Irving – New York Known for his “headless  horseman,” this man of letters totally got it about copyright infringement. If he knew what was happening today, where people assume anything online is publicly owned, he would be leading the charge against the tide of “stealers.”

5. Stephen Crane – New Jersey He pulled writing ideas from his own bohemian lifestyle, accrued serious debt as an over-spender, and had several major illnesses that stemmed from his Bowery days before dying at the age of 28.

6. Benjamin Franklin – Pennsylvania A genius. A scientist. An inventor. Some might even say a wizard. Nothing would stop this man from pushing the boundaries way ahead of his time.

Heading to the South:

7. Edgar Allan Poe – Virginia American literature’s earliest writer of frightful fiction married a 13-year-old cousin when he was 27 and died mysteriously on the road.

8. Thomas Wolfe – North Carolina One of America’s strongest writers had neighbor issues, chose a risky love interest with a woman twenty years older and married, and died of an illness at the young age of 37.

9. Ernest Hemingway – South Carolina This rabble-rousing winner of the Nobel Prize for Literature, and a Pulitzer Prize, was a bull-fighter with several doomed marriages.

10. Stephen Crane – Florida And here he is again, that hard-livin’ writer!

11. Ernest Hemingway – Florida  That same rabble-rouser, only this time you can see just how well he lived in the Shangri-La of Key West!

12. F. Scott Fitzgerald and Zelda Fitzgerald – Alabama This couple was the toast of the town in the Roaring Twenties, but their freewheeling lifestyle caught up with them when the economy collapsed.

13. William Faulkner – Mississippi Too short to serve in the U.S. military, he lied about his birthplace and the spelling of his name in order to serve in the Royal Air Force of Great Britain and later became known for exaggerated war stories. His writing challenged the status quo of The South.

14. The French Quarter – Louisiana (Tennessee Williams, William Faulkner, Jack Kerouac, and more) This was a hot-spot for all sorts of sordid life choices of several major writers.

Moving West:

15. O. Henry – Texas Charged with embezzlement, he fled to New Orleans and then Honduras before serving a three-year prison term in Ohio.

16. Witter Bynner – New Mexico Witter Bynner’s place was Party Central for the likes of D.H. Lawrence, Aldous Huxley, and many other writers, artists, and Hollywood actors.

17. Zane Grey – Arizona Known as the “greatest storyteller of the American West,” he was also known for having a harem of mistresses across the decades of his marriage, including a teenager he dated at age 50.

18. Musso & Frank Grill – California The favorite watering hole for the likes of F. Scott Fitzgerald and William Faulkner still serves the old favorites right on Hollywood Boulevard.

19. Jack London – California Imprisoned at age 18 for vagrancy, he published stories about his experience as a “hobo” before battling the harsh elements of the Klondike in a search for gold.

Jack London Cabin, Oakland, CA ©Author Adventures

20. Caffe Med – California (former location) The home of counter-culture Beat Generation writers and philosophers. Click here for more: Literary San Francisco.

21. Mark Twain – Nevada America’s favorite writer began his newspaper career here and challenged the prevailing perspectives of his day.

22.  Ezra Pound – Idaho Though he had tirelessly supported writers early in their careers, Pound became a pro-Fascist supporter of Benito Mussolini and was confined to a mental asylum in his later years because he was not considered stable enough to stand trial for treason.

23. Buffalo Bill – Wyoming No buffalo had reason to feel safe with this frontier rock star around. He killed more than 4,000 buffalo in his lifetime. And he attracted a lot of women. According to theRochester Morning Herald (1879), “If any lady wishes to behold one of the most perfect and handsomest specimens of manhood in existence, she will have to go and see William F. Cody.” More than 70 million people around the world saw his shows.

24. Theodore Roosevelt – North Dakota Truly a tough guy, Theodore Roosevelt dealt with the grief of losing his mother and wife on the same day by heading alone to the Badlands frontier of North Dakota,  which built up his bravery, courage, and physical health. Later he took charge of the Rough Riders in Cuba and then became a United States president after President William McKinley was assassinated. When Roosevelt was president, he had no vice president.

Traveling to the Midwest:

25. Sinclair Lewis – Minnesota His neighbors wanted to kick him out of town because the characters he wrote about sounded a little too familiar.

26. Mark Twain – Missouri America’s favorite writer, who questioned pretty much everything, led readers to do the same.

27. Ernest Hemingway – Illinois There’s that rabble-rousing writer again!

28. Kurt Vonnegut – Indiana His books challenged the status quo and earned a place on many Banned Books lists.

29. Zane Grey – Ohio America’s top writer of Westerns was quite the womanizer during his long marriage.

Returning to the Northeast:

30. Frederic Remington – New York A tough guy who embraced the vigorous lifestyle of the West, including an investment in a saloon, brought us art and writings about cowboy bravado like no  other.

31. John Dewey – Vermont He showed them! Fired from his first job in education because of office politics, he forged on to become one of America’s most influential writers in the education field.

32. Stephen King – Maine In high school, he produced a satirical newspaper called the Village Vomit and went on to become the most successful American horror writer of the late 20th century and beyond. He has also played in a rock band with other writing luminaries. The movie Stand By Me, based on his story The Body, about adolescent boys who discover the dead body of a missing boy, is considered semi-autobiographical.

Click here for the interactive version featuring names, addresses, routes between stops, and pages connected to each marker: Bad Boys of Books National Road Trip Map. If you wonder about the female counterparts to “Bad Boys of Books,” click here for our Pioneering Women interactive map.