Could Steinbeck have written The Grapes of Wrath without spending time in California’s Central Valley? Would F. Scott Fitzgerald’s novels have been the same if he hadn’t met Zelda in Montgomery, Alabama? America’s great authors were enormously influenced by the places they lived and worked and the people they encountered. Join us on a literary pilgrimage across the U.S., from Steinbeck’s Cannery Row to Hemingway’s Key West.

Literary Road Trip — Monterey, CA to Key West, FL

Monterey, California

Your road trip begins in this historic central California town, the setting for John Steinbeck’s comic novels Cannery Row and Sweet Thursday. Stroll down the former Ocean View Avenue (which was nicknamed “Cannery Row” in the novels, and officially given that name in 1958) and take a tour of Pacific Biological Laboratories, aka Doc Rickett’s lab.

Big Sur, California

Make a detour down Highway 1, across the famous Bixby Creek Bridge, and along the breathtaking coastal cliffs to the Henry Miller Memorial Library. The controversial novelist lived in Big Sur, which he called his “first real home in America,” from 1944 to 1962.

Salinas, California

Return to Monterey and take State Route 68 to Salinas, where Steinbeck was born and raised. You’ll want to visit the National Steinbeck Center, a museum and library devoted to his life and works (a Steinbeck Festival is held here every other year).

Walk down Main Street, looking for settings from East of Eden, Steinbeck’s spin on the Cain and Abel story. Stop for a meal at the Steinbeck House, the author’s childhood home, and pay your respects at the Garden of Memories Memorial Park, where Steinbeck’s ashes are buried.

Soledad to Bakersfield, California

Continue along State Route 68 to Highway 101. Head south, passing through the once-lonely town of Soledad, near the fictional ranch where Of Mice and Men was set. Then, cut east via State Route 46 and I-5 to Bakersfield, at the southern end of the Central Valley. Steinbeck was inspired to write his classic novel The Grapes of Wrath after investigating the region’s migrant labor camps (aka “Hoovervilles”) during the Great Depression.

Route 66

Take State Route 58 to Barstow, one of the celebrated stops on legendary Route 66. In The Grapes of Wrath, the peripatetic Joad family fled Oklahoma’s Dust Bowl and traveled along this “Mother Road” in hopes of a better life in California. A veritable time capsule of mid-twentieth-century America, Historic Route 66 is worthy of a dedicated road trip in itself. But if you want to save time, take I-40 east (the interstate follows essentially the same route) and make side trips now and then to explore the iconic highway.

Grants, New Mexico

As you travel east through Arizona and New Mexico, you’ll be passing through prime Louis L’Amour country. This prolific writer of Westerns set 28 of his 86 novels in these 2 states. Make a stop in Grants, one of the settings for L’Amour’s classic Flint (it’s called Los Alamitos in the novel). Old Route 66 is Grants’ main street, worth checking out for its kitschy hotel signs and retro diners. Make a quick detour south to El Pais National Monument to see the striking lava beds and caves described in the novel.

Sallisaw, Oklahoma

Route 66 continues all the way to Chicago, but you’ll say goodbye to the Mother Road in Oklahoma City. Continue on I-40 to Sallisaw and stop in at Sequoyah’s Cabin, built by the Native American who brought literacy to the Cherokee nation by creating a writing system for their oral language. (Not all American literary heroes were novelists.)

Oxford, Mississippi

Follow I-40 to Memphis and then go via I-55 and US 278 to the picturesque town of Oxford. Here lived William Faulkner, a writer practically synonymous with the South. Pay a visit to Rowan Oak, the stately mansion that was his home for more than 40 years. You can still see the plot outline of his novel, The Fable, handwritten on the wall of his office.

Montgomery, Alabama

Continue east and connect with I-22. Head southeast to Birmingham, then take I-65 south to Montgomery. In 1917, during World War I, F. Scott Fitzgerald was stationed here at Fort Sheridan. He met his free-spirited wife Zelda Sayre the same year, most likely at a dance at the Montgomery Country Club, though some reports say they met at afternoon tea at Winter Place, an antebellum mansion (454 Goldthwaite Street). Be sure to explore the F. Scott and Zelda Fitzgerald Museum, located in the home where the couple lived for several months from 1931 to 1932.

Monroeville, Alabama

Continue south on I-65 to Evergreen and then southwest on State Route 21 to Monroeville. Harper Lee, author of the beloved novel To Kill a Mockingbird, was born and raised here. Stop in at the Old Courthouse (now a museum), which served as the model for the novel’s courtroom scenes. Then go for a milkshake at Mel’s Dairy Dream (216 South Alabama Avenue), which occupies the spot where Lee’s childhood home once stood. Look for the remains of a rock fence next door — it used to belong to the home of the Faulk family. Novelist and playwright Truman Capote lived here with his Faulk cousins when he was a boy. He and Lee became fast friends.

Orlando, Florida

Get on US 84 and head to Orlando via I-10 and I-70. Your next stop is 1418½ Clouser Avenue, the cottage where Jack Kerouac lived for several months in 1957 and 1958, and where he wrote Dharma Bums, his sequel to On the Road. The cottage is now owned by the Kerouac Project, which offers a residency program for writers.

Key West, Florida

Take Florida’s Turnpike and State Route 1 across the Overseas Highway to Key West, the laid-back, subtropical isle where Ernest Hemingway lived, worked, drank, and boxed from 1928 to 1939. His novel To Have and Have Not is set here, and he wrote many of his other well-known works in the studio next to his villa at 907 Whitehead Street, now the Ernest Hemingway Home & Museum.

Stop in at the villa, famously home to dozens of 6-toed cats. Then, pause for a beverage at Sloppy Joe’s Bar (201 Duval Street), where Hemingway was a frequent patron. The character of Freddy in To Have and Have Not was modeled after Joe Russell, the former owner of Sloppy Joe’s.


Can’t get enough literary travel? Take our coast-to-coast northern road trip. And make sure you have reliable car insurance to get you there.

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about Ellen

Ellen has spent many years as a professional wordsmith, helping to shed light on such topics as world travel, cargo pants, and the porosity of bath tiles. As a freelance copywriter for Esurance, she brings her boundless curiosity to the world of insurance. Outside work, she can be found cheering on the San Francisco Giants, hiking in the Oakland hills, and (barely) resisting smuggling penguins home from Antarctica.