From Covered Wagons to Jeeps: The History of the American Road Trip

Our 5,000-mile journey was like driving through a time capsule of the American road trip, following the trails, roads and highways that carried travelers west—from the Oregon Trail to Route 66.

An old covered wagon with yellow wheels sits in the foreground, with a white Jeep in the background, showing the contrast in the history of the American road trip.

The History of the American Road Trip Starts Here

I’ve always wanted to take a long road trip out West, but it wasn’t until I started planning my route through a partnership with Jeep that I realized the quintessential American road trip has a much longer history than I realized—one that began long before Americans had automobiles.

For hundreds of years, people have traveled across the country in search of new opportunities and the unknown. The desire to see what lies beyond the next horizon has always been a driver, both then and now, but the methods of transportation have changed dramatically.

The farther we drove in our modern cross-country road trip, the more I compared our smooth and speedy progress with the tedious journey of the early travelers, who spent months (and years) taking the same route.

Come along and get a feel for this grand adventure that goes through all of the transportation changes that helped create the American road trip we know it today.

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A brown sign that describes the wagon ruts that were left by pioneers along the Oregon Trail. — A sign describing the wagon ruts that are still visible along the Oregon Trail in Guernsey, WY.

The Oregon Trail and Westward Travel

You probably recall from your history lessons that the Oregon Trail became one of the most important overland routes for Americans heading west during the 19th century.

Beginning in the Missouri River region, the trail stretched roughly 2,000 miles toward Oregon’s Willamette Valley. Travelers typically made the journey by wagon, following established trails through what are now several states.

Travelers had to contend with weather, river crossings, limited supplies and mechanical problems involving their wagons and equipment. When you see the terrain, you can’t help but wonder how they made it!

For history lovers, it’s a true blessing to be able to see portions of the Oregon Trail that remain visible. To me, it serves as proof that this page out of our history books really happened.

A photo showing the sunken ground in Guernsey, WY that was caused by the wagon wheels of the pioneers who took the original American road trip. — The wagon ruts created by America’s pioneers are still visible today.

We visited the Oregon Trail Ruts near Guernsey, Wyoming, where the passage of thousands of wagons left the deep marks in the landscape that you see above.

The site takes you on a short walking path where you can see the ruts as well as scenic views of a spectacular landscape.

The next stop for us was Register Cliff, which preserves another reminder of the people who traveled the route.

A brown sign that says Register Cliff Historical Site, with the cliff in the background. — You can see the cliff rising in the background where pioneers signed their names and the year they made it to this site.

Closeup of some names carved into the rock of Register Cliff, a site that shows the history of the American road trip. — A closeup of some of some of the names carved into the cliff by the country’s original travelers. The cliff serves as a register of our early pioneers.

The cliff rises out of the terrain, and was a major stopping point for weary travelers. This landmark became a place to engrave their names, the country they were from, and the date. It now stands as a true register and record of our earliest pioneers.

A covered wagon is seen with the original buildings in the background of Fort Laramie, a must-see on any American road trip out West. — A wagon stands in front of original buildings at Fort Laramie.

An original building that has been restored at Fort Laramie is a two-story white wood structure. — You can go inside this beautifully restored original building at Fort Laramie.

Military Roads and Frontier Forts

As I learned during our American road trip adventure, westward travel also depended on military forts and the transportation routes that resulted from a military presence.

These locations provided places for soldiers and travelers to obtain supplies, communicate and rest.

I had Fort Laramie in Wyoming on my itinerary, but I didn’t expect to spend hours there—which we did! Originally established as a private fur-trading post, it later became a U.S. military post and an important landmark for travelers heading west.

Farther south, Fort Garland in Colorado served as a military post protecting transportation routes and communities in the region. It was another great stop.

Insider Tip: Both of these forts are dog-friendly, which was a welcome relief after visiting several National Parks that do not allow pets.

A white jeep is parked beside a sign that says Fort Garland Museum, past of the history of the American road trip. — Fort Garland is an interesting stop to help learn about the early frontier.

Railroads Transform the American West

Railroads came along and dramatically reduced the time required to cross the country and connected previously isolated communities with national markets.

Towns naturally developed around the railroad lines, and people who once faced months of travel by wagon could make long-distance journeys much more quickly by train. (Although it still wasn’t a very comfortable ride).

Old gas pumps are lined up at an antique store. — Old gas pumps.

The Automobile Changes American Travel

Then came the automobile.

Unlike trains, automobiles did not require travelers to follow a fixed railroad route. As roads improved and automobile ownership increased, Americans gained greater freedom to determine where and when they traveled.

Road construction expanded during the early 20th century, eventually creating networks that connected states and regions.

The automobile also changed tourism. Families could travel for pleasure and explore new destinations. Businesses sprang up to serve motorists, including gas stations, restaurants, tourist attractions and motor courts.

All of these innovations eventually led to the road becoming a destination in itself.

A Route 66 site called Teepee Curious, an original site along this historic road. — Driving Route 66 is so much fun. You never know what you’ll find.

Route 66 and the Rise of Road-Trip Culture

Route 66 became one of the best-known symbols of the American road trip.

Established in 1926, the highway originally stretched from Chicago to Los Angeles, crossing Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California.

Over time, the businesses that developed along the highway became part of its identity. Gas stations, diners, motels and roadside attractions catered to motorists and helped create a distinctive road-trip culture.

A white jeep parked in front of a Route 66 sign during a great American road trip. — Couldn’t resist pulling the Jeep into this Route 66 station.

A lighted Route 66 gas station called the tower in Shamrock, Tx., with a Jeep parked there. — This station is called The Tower, and is located in Shamrock, Tx.

Although Route 66 was removed from the U.S. Highway System in 1985, portions of the original route remain accessible and have become historic destinations themselves.

If you have the opportunity, jump on Route 66 (running parallel with Route 40), whenever you can. There are places that pretty dead, but there are a lot of things to see in certain regions.

It’s so much fun to explore and see how the history of the American road trip began.

Looking at the attractions, you can see why traveling became an experience rather than simply a way to reach a destination.

Three ducks sit on a dashboard while going through an iron bridge. — Even the architecture on this historic road trip was interesting.

From Highways to Scenic Byways

The American road trip we took covered 15 states over two weeks and included a lot more than interstate highways.

We took scenic byways, historic routes and local roads that gave us landscapes that were every bit as spectacular as the sites that are seen in touristy areas.

Ducks sit on a dashboard, with a winding road and mountains in the distance. — The mountain scenery was spectacular.

Traveling With Pets

We’ve done short trips with our rescue dog, but this is the first long one. It was definitely something that adds extra obstacles, but I was surprised at how smoothly it went.

I’ll have to write a whole post about what we learned from the experience.

A woman walks a dog past a white Jeep. — Our rescue dog Sophie was a real trooper on this long Jeep road trip.

Pet-Friendly Hotels We Encountered:

El Rey Court in Santa Fe, N.M.: Excellent amenities and very spacious room with a fireplace! Also excellent dog-walking area. Highly recommend.

The Historic Taos Inn in Taos, N.M: I love historic hotels, but I can’t recommend this one. A bit noisy from the lobby and bar, small rooms, and we had a non-working television and barely-functioning air conditioner.

My Place Hotel, Sioux Falls, S.D.: A nice, clean hotel in a quiet area of town (although close to a highway). I like being a little closer to a downtown so I can explore, but this hotel’s bed was extremely comfortable, so no complaints.

The Stampmill Victorian Suites in Lead, S.D.: We wanted to stay in Deadwood, but there was a festival so we ended up in Lead, just a few miles away. Staying in a former brothel and eating at the saloon downstairs was an awesome (and very different) experience.

Badlands Hotel and Campground in Interior, S.D.: This is an old hotel and campground that is located right next door to the Badlands National Park. They have a fenced area for dogs and a camp store for supplies (and wine). I found the check-in person to be a little rude, but our stay was convenient and comfortable.

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The American Road Trip Continues

From covered wagons to Jeeps: I can’t help but compare how traveling by automobile is so dramatically different from the brave souls who forged through the wilderness in the 1800s.

When you’re thousands of miles away from home on an American road trip, you realize what we take for granted: air conditioning, navigation systems, communications, safety features and on-demand music!

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We can travel farther, faster and more comfortably now, but thankfully, the landscape remains relatively untouched and the small communities that shaped earlier journeys are still there.

That is probably the best part of this adventure and is what makes a modern road trip through historic America so interesting.

The vehicles are different. The roads are better. But the spirit of the journey remains the same: crossing the country, exploring along the way and discovering the history that shaped America.

Many thanks to Jeep for the loan of a Jeep Grand Cherokee for this trip. And many thanks to the folks at Brown’s Ford in West Branch, Iowa, for their help during the trip.

Plan Your Trips With Roadtrippers

I honestly could not plan a trip this big without Roadtrippers, but I use it for my smaller trips too.

As you can see, it helps you visualize the trip, gives you the distance in time and miles between stops — most importantly for me, gives me suggestions on things to see along the way.

I can’t even count the number of places I’ve stopped that I would never have known about without Roadtrippers. It can also show you hotels and unique stays.

You can try it for FREE with this link.