Literary Road Trips

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  • East Coast
  • The South
  • Midwest
  • Northwest and Southwest
  • Roadside assistance
From the prairies of Laura Ingalls Wilder to Jack Kerouac’s meanders across the country, America is full of stories. Relive your favorite book—or discover a new one—by retracing the author’s route on your next road trip.
Our country is so big that every corner has its own unique literary flavor. The East Coast is fond of haunted fiction and dramatic poetry while the Pacific Northwest is all about nature and the pioneering spirit, to name a few.
Wherever you live, there is probably a great American literary road trip located a few hours’ drive away. Before you go, get Jerry’s help finding cheap car insurance with a roadside assistance membership—so you can adventure with the confidence of your favorite hero or heroine.
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East Coast

Massachusetts: Little Women by Louisa May Alcott

Whether you read the book or watched one of the movie adaptations, Little Women is one of the most beloved American novels of all time.
The author is Louisa May Alcott, and you can visit Alcott’s home in Concord, Massachusetts to get a firsthand glimpse into the world of the novel.
Less than one hour outside of Boston, this is the perfect literary road trip destination if you only have one day to spend exploring.
Orchard House is the name of the Alcott family home in Concord, and it is here that she penned the majority of the famous book. The site is open to visitors year-round and you can walk the grounds or enjoy a tour inside—including the desk where she sat to write.
Of course, the characters of Meg, Jo, Beth, and Amy are imaginary but it’s not difficult to imagine the fictional sisters playing and fighting on the real Alcott land in Concord.
The surrounding area with its classic hillsides and streams is straight out of the novel. Don’t leave without visiting the Sleepy Hollow Cemetery where Alcott is buried along with other famous New England writers.
Concord, Massachusetts
Concord, Massachusetts

Small towns on the East Coast (and beyond): The Lost Continent by Bill Bryson

Author Bill Bryson traveled more than 5,000 miles to write this classic and entertaining book about life in small-town America.
You may have strong feelings about Bryson’s perspective, but it’s definitely worth doing this road trip to see for yourself. The best part of this route is that it avoids the big cities in favor of lesser-known areas. Originally published in 1989, the book’s destinations have likely changed immensely in the past 30 years.
Travelers can choose their own adventure with this literary road trip.
Bryson meandered through 38 states, from the Mississippi River to Des Moines, Iowa. Either reread the book and follow his route, or chart your own path on the backroads. For a truly authentic experience, don’t stop over anywhere that has a population greater than 10,000.
Des Moines, Iowa
Des Moines, Iowa
Key Takeaway A literary road trip doesn’t have to follow the literal route—use your imagination!
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The South

Georgia: Gone With the Wind by Margaret Mitchell

Margaret Mitchell’s fictional novel is a fascinating glimpse into a spoiled Southern girl’s experience of this historic era in our country’s history.
You can shape your literary road trip around the destinations mentioned in the book as well as sites relevant to the author herself.
Clayton County is where the story is set and there are plenty of self-guided tours to set you on the right path.
Film aficionados will enjoy a visit to Marietta’s Gone With the Wind Museum, which includes costumes, set decoration, and other memorabilia related to the movie. There are great exhibits on Antebellum architecture which inspired Mitchell.
Head to Atlanta to visit The Margaret Mitchell House where she penned the novel in the 1930s. There are regular guided tours for literary fans, as well as occasional events that celebrate the author and the work’s place in history.
Superfans should also visit the Atlanta-Fulton Library’s Central branch, which has on display Mitchell’s very own typewriter as well as her library card. Swing by the Atlanta History Center to brush up on Civil War history if you’re a bit rusty. Finish your trip at Oakland Cemetery in Atlanta, where Mitchell is buried.
You can also visit Jonesboro’s Road to Tara Museum, which offers a bus tour and stories about the real people who inspired the novel.
Atlanta, Georgia
Atlanta, Georgia

Florida and Alabama: Zora Neale Hurston

Zora Neale Hurston was an incredible African-American writer and anthropologist. Her most famous work is the novel Their Eyes Were Watching God, but she also penned plays, short stories, and non-fiction essays.
Hurston was a fixture of the Harlem Renaissance in New York City, but her literary adventures in the South make for a much more interesting road trip.
Follow in the steps of this great American writer of the 1900s by traveling first to Eatonville, Florida, only 10 miles from Orlando. This is the first town in America to be independently governed by African-Americans, and it’s also the home of The Zora Neale Hurston Museum.
It pays tribute to her work and her family. Nearby, you can also visit her haunts in Belle Glade and another “trail” in Fort Pierce dedicated to honoring Hurston’s work in the area.
If you have time for one more jaunt, retrace the road trip that Hurston took with her friend Langston Hughes from Mobile to Tuskegee.
Fort Pierce, Florida
Fort Pierce, Florida

Mississippi and Missouri: The Adventures of Huckleberry Finn by Mark Twain

This picturesque literary road trip is within a few hours of most major cities in the area. Start in the town of Hannibal, Missouri on the Mississippi River, the birthplace of author Mark Twain.
Here, you can visit Twain’s childhood home and even take a spin on a riverboat. There’s a Tom and Huck statue as well as a memorial lighthouse honoring Twain. Close readers will recognize many landmarks around town that make a fictionalized appearance in the novel.
The Hannibal Trolley Co. offers quaint trips into the countryside, and it’s the perfect way to enjoy the sights without having to get behind the wheel yourself.
Now, head to the Mark Twain Caves. It’s nice and cool inside, and there are audio narrations that make you feel like you’re a character from the novel looking for treasure.
The River plays a major role in the book, so make sure you leave plenty of time on your literary road trip to meander the back roads and discover your own quiet riverfront nook.
Key Takeaway Leave plenty of time to explore historic landmarks on your literary road trip.
Hannibal, Missouri
Hannibal, Missouri

Midwest

Wisconsin, Minnesota, and more: Little House on the Prairie by Laura Ingalls Wilder

If you grew up reading about Ma, Pa, and Laura’s adventures on the prairie, then you’re in for a shock—you can visit the exact locations where the Wilder family attempted to carve out a living.
Here is a step-by-step guide, but we’ll outline the general route below.
Start in Pepin, Wisconsin. There’s a replica of the Wilder family’s log cabin and it’s on the very land where Laura lived as a child.
Inside, you can view tons of artifacts from the early pioneer days of Pepin. Of course, the best part is seeing the countryside and imagining what life must have been like for young Laura.
If you’re a diehard fan, follow the trail (er, highway) south to Independence, Kansas—a trip that will take you nine short hours on smooth pavement, versus the Wilder family’s slog on a covered wagon.
Here, the family built an illegal cabin on Indigenous land and had to leave after just a short time. They returned to Pepin for a time before moving on to Walnut Grove, Minnesota.
Prefer to visit only the main sights? Go from Pepin to Walnut Grove, less than a four hours’ drive away. This is where the family set up on Plum Creek, and where Pa was eventually able to build a real home (with glass windows!) for the family.
Other books in Wilder’s series take place at the next stop, two hours west in De Smet, South Dakota.
This was the last family home of the family. There’s a delightful living farm here where you can see Ingalls artifacts, drive a covered wagon, and explore a pioneer schoolhouse. By Silver Lake, you can visit the cottonwood trees that Pa planted. You can even pay your respects at their gravestones.
Pepin, Wisconsin
Pepin, Wisconsin
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Northwest and Southwest

Washington and Oregon: Wild by Cheryl Strayed

Of course, you can’t drive on the famous Pacific Crest Trail from Strayed’s novel. However, you can road trip through the major landmarks and perhaps even do some PCT day hikes.
Start at Cascade Locks on the Columbia River on the border between Washington and Oregon.
If you’ve seen the film, you’ll recognize the bridge immediately. There’s a small restaurant nearby with parking if you want to walk across by yourself, but you will have to pay a small fee (only thru-hikers walk free).
If you roughly follow Oregon’s Highway 26, you will stop at Warm Springs. Adventurers with sturdy vehicles can veer off to Olallie Lake and spend the day swimming and hiking where Strayed stayed. Otherwise, continue a few more hours to McKenzie Pass—and be grateful you’re not making the journey on foot.
You can retrace her steps all the way to California via the PCT, but a good conclusion for this literary road trip is the Shelter Cove Resort. Rent a cabin on Odell Lake and enjoy a less extreme wilderness experience before you head home.
Cascade Locks, Columbia River
Cascade Locks, Columbia River

Montana: A River Runs Through It by Norman MacLean

If your idea of a great road trip is 10% driving and 90% fishing, then this trip is for you.
Western Montana is the beautiful backdrop for MacLean’s novel, and it makes for great road-tripping scenery. It’s set in Missoula and on the Blackfoot River (note that the movie was filmed elsewhere).
When the book came out, the Blackfoot was incredibly polluted. The attention from the novel (and the film) inspired conservation efforts that have restored the river to a healthy state.
Start in Missoula where the Blackfoot branches off from the Clark Fork. Follow Highway 200 east along the river and you can choose from any number of beautiful spots to pull over.
McNamara is the last place to stop before the road leaves the riverside for a short stretch. Otherwise, the road reunites with the Blackfoot on the other side of Morrison Peak at Barite.
You could follow the river as far east as Powell County (an hour away) if you like.
Pacific Crest Trail, Oregon
Pacific Crest Trail, Oregon
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Roadside assistance membership

Being adventurous is admirable, but being unprepared? That’s just silly.
Besides providing car insurance quotes, Jerry now offers a roadside assistance membership program featuring emergency lockout assistance, Uber credits with towing services, and up to four covered roadside events per year.
Jerry’s emergency roadside assistance offers a slew of services to set things right, in case you find yourself and your car in the lurch. You’ll have emergency jumpstarts, fuel delivery, tire changes, and vehicle towing up to 10 miles (and more), at your fingertips if the need arises.
The exclusive benefits aren’t too shabby either. If your car needs to be towed, you’ll get up to $25 in Uber credits to help get you where you need to go.
Not to mention up to $100 for key replacement, and up to $100 in tire repair per incident, amongst other perks, to help ease the financial pain of any roadside issues.
With Jerry roadside assistance, up to four roadside events are covered under your plan, but with any luck, you won’t have any issues while driving. Just peace of mind (and great roadside coverage) in the event that something does go wrong.
Before you head out, make sure your car insurance is up to date and that you’ve got all the road trip essentials.
Happy travels!
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