Experience America’s Ultimate Historic Road Trip: A Spectacular Cross-Country Adventure Through Iconic Landmarks

For many Americans, road trips are something of a way of life. Because we’re so obsessed with the freedom of the open road, nothing ignites our passion for travel quite like a trip across the various highways and freeways of the country. Best of all, with so many states, cities, and iconic landmarks to choose from, you can customize your road trip as much as you want.

But while road trips are generally a good way to see different parts of the U.S., nothing really compares to a cross-country adventure. There are many ways to do this, but one of the most unique options allows you to stay on one freeway practically the entire way while still seeing some of the most historic and iconic sights the country has to offer.

This epic journey begins in Los Angeles, California, and ends in Charlottesville, Virginia. Along the way, you’ll run into America’s oldest capital city, the priciest city in which to rent a car, and the home of a wildly lavish resort that’s a destination in its own right. All while mostly staying on one freeway: I-40. So, pack your trunk, fill your gas tank, and let’s hit the road!

Depending on where you currently live, you might have to fly into LAX or drive into the City of Angels to start your road trip expedition. If you’re renting a car, the total trip is about 2,600 miles, although that number may fluctuate depending on which sites you plan to visit along the way.

Technically, you could easily spend up to a week in LA since there is so much to do and see. First, there are all the theme parks in the area, including Universal Studios Hollywood and Disneyland. However, if you want something a bit more unique to the city, you can check out LA’s “smelliest experience,” the unique fossil museum of the La Brea Tar Pits.

Los Angeles is also a foodie paradise, with a fantastic smorgasbord of options to sate even the pickiest eaters. If you want to kick off your road trip with an epic meal, may we suggest dining at the Musso & Frank Grill, a timeless, tasty gem that happens to be Hollywood’s oldest restaurant. Alternatively, you can indulge your taste buds with less decadent fare like Pink’s hot dogs, a sandwich from Johnnie’s Pastrami, or the ever-classic In-N-Out Burger.

After filling your belly with delicious food and your mind with rich history, it’s time for the next roughly 13-hour leg of the road trip to reach Little Rock, Arkansas. Since you only have to stay on I-40, you don’t have to worry about getting lost or downloading directions. That said, along the way, you may want to stop at one of the best Route 66 attractions — the Cadillac Ranch in Amarillo, Texas — to see the row of spray-painted vintage sedans protruding from the earth like jagged teeth. Then, you may want to stop in one of the best cowboy cities in the United States, Oklahoma City. While there, you can venture to the unique, vibrant tunnel of art hidden beneath the streets, or you can let off some steam at Frontier City theme park.

If you’ve never been to Little Rock before, it’s nothing like what you might expect. Although the city seems like it’s in the middle of flyover country, it’s actually a thriving metropolis next to the mighty Arkansas River. In fact, one of the best areas to check out during your visit is the artsy gem of boutiques, markets, and food that is the River Market District. While you’re in the area, you can learn about Arkansas’s history at the Old State House Museum, the Historic Arkansas Museum, and the Clinton Library and Museum.

Little Rock is also something of a beer lover’s paradise, meaning you can partake in a pretty epic pub crawl. There are numerous breweries and craft beer houses in the city, such as Lost Forty Brewing, Southern Tail Brewing, and Stone’s Throw Brewing. But if you’re hoping to sample as much beer as possible, go to the Flying Saucer Draught House. If you’re into liquor, there’s Rock Town Distillery, or if you want a beer hall with German flair, there’s Fassler Hall.

If driving 13 hours between cities is getting a bit overwhelming, don’t worry. The next leg of this epic road trip is just about six hours to reach Nashville, Tennessee. However, since I-40 also flows through Memphis, you may want to stop in both cities to get as much country music culture as possible. If you do stop in Memphis, be sure to check out Elvis’ former home Graceland, America’s largest manmade crystal cave (the Crystal Shrine Grotto), and Beale Street. Beale Street is full of bars, shops, and restaurants, but one of the most notable is Dyer’s Burgers, which has been using the same grease for over 100 years.

But if you’re really into country music, there’s no better place to experience it than in Nashville. The heart of the city is home to numerous live music venues and bars where you can hear twangy Southern guitars and banjos practically every night. Some of the biggest stages in Nashville include Ryman Auditorium, the riverfront venue of Ascend Amphitheater, and, of course, the Grand Ole Opry. If you’re visiting the Opry, you must also check out the Gaylord Opryland Resort and Convention Center, an upscale resort complex featuring top-tier amenities like an aquatic park, spa, fitness center, and proximity to some of the best music in the city. 

Since history is a big part of this trip, you can blend both music and learning while you’re in Nashville. There’s the Country Music Hall of Fame, the Johnny Cash and Patsy Cline Museums (next door to each other), and the Musicians Hall of Fame. For more traditional history, you can visit the Nashville Parthenon, a replica built in 1897 of the Greek icon, or you can stroll through the Civil War ruins of Fort Negley.

Our final stretch is the roughly eight-and-a-half-hour drive from Nashville to Charlottesville, Virginia. Why is Charlottesville our final stop on this magical history tour? Well, it’s the site of Monticello, the famous home of the third U.S. president, Thomas Jefferson. Plus, there are many other museums and historical sites like the Albemarle Charlottesville Historical Society, James Monroe Highland, where the fifth president lived, and the Lewis and Clark Exploratory Center. The city is also home to the University of Virginia, founded in 1819 by Jefferson.

Charlottesville is also an excellent stop if you want to experience nature and stretch your legs. There are tons of parks and green spaces in and around the city, including the Lawn, which was designed by Thomas Jefferson. There’s also Forest Hills Park, Benjamin Tonsler Park, Riverview Park, Darden Towe Park, and McIntire Park, among others. Many of these parks include playgrounds, pools, water slides, picnic areas, and more.

You can also combine history with delicious food. Two of the best places to do this are the Monticello Cafe and the Michie Tavern, which was built in 1784. At Monticello, you can choose from craft sandwiches to vegetarian dishes. At Michie, dinner is a full-course meal with fried chicken, pulled pork, and a variety of old-fashioned side dishes. If you want a mix of modern and historic, you can stroll down Main Street in the Historic District, which features a wide variety of restaurants and shops.

When planning any kind of cross-country road trip, it’s almost impossible to choose destinations without leaving at least a few on the cutting room floor. Since this road trip was all about history, we chose cities that have compelling historical significance but may not be on anyone’s radar. It’s easy to choose cities like Boston, Washington, D.C., and Philadelphia for American history, but the country is a rich tapestry of cultures, traditions, and sites.

Another element that influenced our decision-making process was the fact that we wanted to stick to I-40 for much of the journey. Like Route 66, I-40 passes through some incredible cities and historical sites, and it serves as a fantastic throughline for planning a road trip. Plus, compared to other interstate freeways, I-40 offers an excellent variety of states, cities, and climates.

Overall, these stops should give you a comprehensive look at the cultural, geological, and geographic history of the United States. At each point, you can see how different factors have influenced the nation’s history and understand and celebrate America’s cultural diversity.