10 Classic Road Trips in the U.S. That Will Take You Back in Time

Taking a road trip is a right of passage in the U.S., with millions of people hitting America’s most famous roads each year. We explore 10 road trips that offer a glimpse into America’s past and tell stories of the country’s origins and cultural evolution. Whether it’s the scenic beauty of coastal highways or winding routes through historical towns, these classic journeys will transport you back in time: 

Route 66,  The “Mother Road”

Starting in Chicago, Illinois and ending in Santa Monica, California, Route 66 had to be the first road trip on this list. The iconic road trip, known as the “Main Street of America,” reaches almost 2,500-miles, journeying through the heartland and taking you back to a time when classic diners, motels and quirky roadside attractions were the norm. Your trip will take you past historic towns like Amarillo, Texas and Flagstaff as well as the historic town of Seligman in Arizona where time seems to have stood still.

The Blue Ridge Parkway

Winding through the Appalachian Mountains, the Blue Ridge Parkway is often referred to as “America’s Favorite Drive.” This 469-mile scenic route offers stunning views, historic landmarks and access to a wealth of cultural history, ending in  Cherokee, North Carolina.  The drive offers a trip through Civil War sites and Appalachian communities and the historic Mabry Mill, a historic gristmill built in the early 1900s.

The Natchez Trace Parkway

Following an ancient Native American trail, the Natchez Trace Parkway takes drivers through 444 miles of Southern history. Starting in Natchez, Mississippi and finishing in Nashville, Tennessee, this trail was once a critical trade route. The road now offers travelers a peaceful and scenic journey past Civil War battlefields, Native American burial mounds and charming Southern towns. The ghost town of Rocky Springs, a remnant of the Old South, is a highlight of this road trip, where you learn of the stories of its former residents.

Pacific Coast Highway

Also known as California State Route 1, the Pacific Coast Highway offers one of the most dramatic and picturesque drives in the country. As you cruise along the rugged coastline of Big Sur and explore historic towns like Monterey and Carmel-by-the-Sea, you’ll feel as though you’ve stepped back in time to a slower, more romantic era of San Francisco through to San Diego.. Be sure to visit Hearst Castle in San Simeon, a lavish estate built in the early 20th century that captures the opulence of a bygone era.

The Lincoln Highway

Starting in Times Square, New York City and ending in  Lincoln Park, San Francisco, The Lincoln Highway was one of the first transcontinental highways in the U.S. This 3,000-mile road trip takes travelers through the heart of the country, passing historic landmarks such as the Gettysburg Battlefield and the Nevada desert’s eerie stretches. Road trippers can take a detour to visit the Field of Dreams in Iowa, a relic from the past that still evokes nostalgia.

The Great River Road

Following the course of the mighty Mississippi River, the Great River Road is a scenic route  from Lake Itasca, Minnesota to New Orleans, Louisiana. This route is steeped in history and  covers 10 states and thousands of miles, winding past antebellum mansions, historic Civil War sites and sleepy river towns. Many people make a stop at one of the historic plantations near Vicksburg, Mississippi to learn about the history of the South. 

Route 1, Maine’s Coastal Byway

Maine’s Coastal Route 1 offers a step back into the maritime history of New England, stretching from Kittery to Calais. As you travel along the Atlantic coastline, you’ll encounter quaint fishing villages, lighthouses and old shipyards. The route is dotted with charming inns, historic buildings, and the picturesque seascapes that once inspired early American artists. Don’t miss a stop in the historic town of Camden, where Victorian architecture and a bustling harbor transport you back to the 19th century.

The Black Hills and Badlands, South Dakota

This classic road trip takes you through South Dakota’s Black Hills and Badlands, a region rich in Native American history, Wild West legends, and geological wonders. Along the way, you’ll see Mount Rushmore, the historic town of Deadwood, and Crazy Horse Memorial, capturing the rugged spirit of the Old West. One highlight of the trip is exploring Deadwood, the legendary frontier town that once was home to Wild Bill Hickok and Calamity Jane.

Historic Columbia River Highway

Built in the early 20th century, the Columbia River Highway is a marvel of engineering and one of the country’s oldest scenic byways. As you drive along this historic road, you’ll be treated to stunning views of waterfalls, cliffs and the Columbia River Gorge. The highway runs from Troutdale to The Dalles and offers a unique glimpse into the early days of American road building and the natural beauty that captivated travelers of the time. Stop at Multnomah Falls, Oregon’s tallest waterfall, which has been a tourist attraction since the highway’s opening.

The Loneliest Road in America, U.S. Route 50

Spanning coast to coast, U.S. Route 50 was dubbed “The Loneliest Road in America” by Life magazine, but it’s also one of the most historically rich routes. This road trip will take you from Ocean City, Maryland to Sacramento, California, through ghost towns, desolate deserts, and forgotten mining communities. This route offers a haunting glimpse of America’s past. The old mining town of Ely, Nevada, captures the spirit of the Gold Rush era, complete with a historical railroad that once served the mines.