A Literary Road Trip Through the Midwest: Wander Through America’s Storybook Heartland
There’s something about the American Midwest that has always spoken to writers. Maybe it's the endless horizons, the resilient communities, or the way time seems to linger a bit longer in the small towns and prairies. Whatever it is, this region has given rise to some of the most iconic voices in American literature.
So why not swap out your usual beach getaway for a road trip that takes you deep into the pages of America's greatest novels?
Pack your bags—and your favorite books—and get ready for a literary-inspired road trip through the Midwest. From the rolling hills of Missouri to the sweeping plains of Nebraska, this route lets you walk in the footsteps of Mark Twain, Willa Cather, F. Scott Fitzgerald, and others who turned the Midwest into literary gold.
Stop 1: Hannibal, Missouri – The Boyhood Home of Mark Twain
Book Pairing: The Adventures of Tom Sawyer
Mileage from St. Louis: ~120 miles northwest
Start your trip where American storytelling arguably began: the river town of Hannibal, Missouri. This was the childhood home of Samuel Clemens, better known as Mark Twain. Walk the banks of the Mississippi River and imagine Huck Finn pushing off on his raft, or Tom Sawyer plotting his next escapade.
Must-See:
Mark Twain Boyhood Home & Museum Complex – Includes his childhood house and a replica of Becky Thatcher’s home.
Lover’s Leap – A scenic overlook with a view of the Mississippi that looks straight out of a Twain novel.
Literary Fun Fact: Twain once said, “I never let schooling interfere with my education”—a sentiment you’ll feel in every rustic brick and creaky floorboard of Hannibal.
Stop 2: St. Paul, Minnesota – Where the Jazz Age Sparked
Book Pairing: The Great Gatsby
Mileage from Hannibal: ~470 miles north
F. Scott Fitzgerald was born in St. Paul, and though his novels are often associated with New York and Paris, the polished elegance and rigid social codes of Gatsby’s world started here.
Must-See:
F. Scott Fitzgerald House (599 Summit Ave.) – A National Historic Landmark and one of many stunning homes on this grand boulevard.
Cathedral Hill Neighborhood – Perfect for a Gatsby-style photo op.
Pro Tip: Grab a whiskey at The Commodore Bar & Restaurant, a 1920s speakeasy-style venue that Fitzgerald himself used to frequent.
Stop 3: Sauk Centre, Minnesota – Sinclair Lewis and the Birth of Satire
Book Pairing: Main Street
Mileage from St. Paul: ~120 miles northwest
Sauk Centre might look like any other quiet Midwestern town, but this is the hometown of Sinclair Lewis, America’s first Nobel Laureate in Literature. His biting satire of small-town life in Main Street made waves and remains eerily relevant today.
Must-See:
Sinclair Lewis Boyhood Home
Main Street Historic District – Yes, it’s a real place.
Literary Insight: Lewis’ depiction of narrow-mindedness in small-town life was controversial, but it opened up a nationwide discussion about conformity and the American Dream.
Stop 4: Red Cloud, Nebraska – Willa Cather’s Prairie Legacy
Book Pairing: My Ántonia
Mileage from Sauk Centre: ~400 miles southwest
Willa Cather’s prose paints Nebraska like a pastoral canvas. Visit Red Cloud to understand how the vast, treeless plains shaped one of the greatest female authors in American history.
Must-See:
Willa Cather Foundation and Red Cloud Opera House
The Willa Cather Memorial Prairie – 600 acres of native prairie that looks exactly like it did over a century ago.
Best Experience: Take a guided tour of the sites mentioned in Cather’s novels—it’s like walking into her chapters.
Stop 5: Monroeville, Indiana – The Quiet Town of Gene Stratton-Porter
Book Pairing: A Girl of the Limberlost
Mileage from Red Cloud: ~750 miles east
An often-overlooked gem, Monroeville is associated with Gene Stratton-Porter, a naturalist and novelist who brought Indiana’s wetlands to life through rich descriptions and strong female characters.
Must-See:
Limberlost State Historic Site – Explore the swamp that inspired so much of her writing.
Nature Note: You’ll spot birds and wildflowers galore—exactly the kind of beauty Stratton-Porter fought to preserve in her writing and her life.
Stop 6: Oak Park, Illinois – The Cradle of Hemingway
Book Pairing: A Farewell to Arms
Mileage from Monroeville: ~200 miles west
Oak Park is more than a leafy Chicago suburb—it’s the birthplace of Ernest Hemingway. While his globe-trotting exploits made headlines, his early years here left an indelible mark.
Must-See:
Ernest Hemingway Birthplace Museum
Frank Lloyd Wright Home & Studio (bonus architecture stop!)
Did You Know? Hemingway hated Oak Park’s conservatism, once saying it was a place of “wide lawns and narrow minds.” Nevertheless, it shaped the stoic, stripped-down style that made him famous.
Optional Final Stop: Chicago, Illinois – The Urban Muse
Book Pairing: Native Son by Richard Wright or The Jungle by Upton Sinclair
Mileage from Oak Park: ~10 miles east
Wind down your trip in the cultural heart of the Midwest. Chicago’s literary scene is gritty, complex, and totally alive. It's the place where realism reigns, and the industrial backdrop sets the tone for novels that wrestle with race, class, and power.
Must-See:
American Writers Museum
The Green Mill Cocktail Lounge – A literary and jazz haunt frequented by Al Capone and poets alike.
Midwest Road Trip Playlist: Music for the Miles
To truly feel the literary spirit of the Midwest, set your Spotify to shuffle with this specially curated Midwest Literary Road Trip Playlist:
“America” – Simon & Garfunkel
“Wagon Wheel” – Old Crow Medicine Show
“Big River” – Johnny Cash
“Dust Bowl Dance” – Mumford & Sons
“Chicago” – Sufjan Stevens
“Midwest Town” – The Secret Sisters
“River” – Leon Bridges
“The Weight” – The Band
“Jack & Diane” – John Mellencamp
“Take Me Home, Country Roads” – John Denver
This blend of folk, Americana, blues, and classic rock captures the rhythms of cornfields, train whistles, and dusty main streets.
Pro Tips for a Literary Road Trip
Bring the Books – Whether you’re listening to audiobooks or reading paperbacks, having the texts with you makes each stop more meaningful.
Stay Local – Book historic inns, B&Bs, or small-town motels for a more immersive experience.
Time It Right – Fall offers beautiful foliage and fewer crowds, while summer brings small-town festivals that celebrate these authors.
This road trip is about more than just sightseeing. It’s about feeling the texture of American literature under your wheels and in your heart. The Midwest isn’t just “flyover country”—it’s the country of Main Street, The Mississippi, The Prairie, and Gatsby’s Lost Dream. It’s a place where fiction becomes geography and stories are as rooted as the corn.
So, whether you’re a bookworm, a history buff, or just someone who loves a great story, this Midwest literary road trip promises inspiration at every stop.
Happy travels—and happy reading.
