1. Route 66 – The Mother Road
You can’t talk about historic American roads without mentioning Route 66. Running from Chicago to Santa Monica, this iconic highway is more than just a road—it’s a cultural journey. Along the way, you’ll find retro diners, quirky roadside attractions, and plenty of photo-worthy spots that scream Americana.
2. The Oregon Trail – Following the Pioneer Spirit
Although you can’t drive the Oregon Trail exactly as the pioneers did, much of the route has been converted into modern highways like U.S. Route 30 and I-84. Along this historic path, you’ll encounter landmarks like Independence Rock and the eerie beauty of Wyoming’s plains. This one’s for the dreamers who wonder what life was like for those brave pioneers.
3. The Natchez Trace Parkway – A Road Through Time
Stretching 444 miles from Nashville, Tennessee, to Natchez, Mississippi, the Natchez Trace Parkway is an ancient path used by Native Americans, European settlers, and even Civil War troops. Today, it’s a peaceful, scenic drive that offers more than just history—think hiking trails, waterfalls, and wildflower meadows.
4. The Lincoln Highway – America’s First Transcontinental Road
Dating back to 1913, the Lincoln Highway was the first road to connect the East Coast to the West Coast. Spanning from Times Square in New York City to Lincoln Park in San Francisco, this road takes you through a variety of landscapes and small towns that still preserve that old-school charm.
5. Skyline Drive – Virginia’s Blue Ridge Beauty
Winding through Shenandoah National Park, Skyline Drive offers 105 miles of some of the most stunning vistas you’ll ever see. It’s more than just a pretty drive though—this road played a role in Civil War history, and you can find old battlefield sites along the way.
6. The Boston Post Road – A Colonial-Era Journey
Dating back to the 1600s, the Boston Post Road was one of the first mail routes in the U.S. Today, it mostly follows U.S. Route 1, connecting Boston and New York City. Along the way, you’ll pass through quaint New England towns and encounter historical markers that highlight its Colonial-era roots.
7. The Great River Road – Following the Mighty Mississippi
For a true American adventure, take the Great River Road, which traces the Mississippi River from Minnesota to Louisiana. Along this 3,000-mile stretch, you’ll drive through 10 states and experience everything from peaceful river views to bustling cities like New Orleans. It’s a road that captures the very essence of American culture.
8. El Camino Real de los Tejas – A Spanish Legacy
Dating back to the 1600s, El Camino Real de los Tejas connected Mexico to Louisiana, playing a key role in Spanish colonization. Now a National Historic Trail, parts of this route can still be driven along U.S. Highway 83, leading you through the heart of Texas and its deep Spanish influence.
9. U.S. Route 1 – From Maine to Key West
One of the longest north-south roads in America, U.S. Route 1 runs from the Canadian border in Maine all the way to the southernmost point of the U.S. in Key West, Florida. This road is a journey through diverse American cultures and landscapes, from the rocky coastlines of Maine to the tropical paradise of the Florida Keys.
10. The Loneliest Road in America – U.S. Route 50
Nicknamed the “Loneliest Road in America” for its desolate stretches, U.S. Route 50 offers an eerie but beautiful drive through Nevada’s desert. While it may feel remote, this route was once a key part of the Pony Express trail, and driving it today gives you a sense of the vastness of the American frontier.
11. The Dixie Highway – A Southern Charm Experience
Built in the early 20th century to connect the Midwest with the southern states, the Dixie Highway is a collection of roads that stretch from Michigan to Florida. It’s a must for history lovers, with plenty of Civil War landmarks and charming Southern towns along the way.
12. The Pacific Coast Highway – A Scenic Marvel
If jaw-dropping views are your thing, then driving the Pacific Coast Highway (PCH) is a no-brainer. Stretching along the California coast from San Diego to San Francisco, this iconic road was originally built in the 1930s and offers views of the Pacific Ocean, cliffs, and coastal towns like Big Sur and Monterey. Plus, the sunsets? Absolutely breathtaking.
13. U.S. Route 20 – America’s Longest Road
Running from Boston to Newport, Oregon, U.S. Route 20 holds the title of America’s longest road, clocking in at 3,365 miles. Along this massive stretch, you’ll pass through Yellowstone National Park, charming Midwestern towns, and eventually, the rugged Oregon coast. It’s the ultimate cross-country adventure.
14. The Trail of Tears National Historic Trail – A Somber Journey
While it’s not an easy trip emotionally, the Trail of Tears National Historic Trail is an important route to experience. Following the forced relocation of the Cherokee people in the 1830s, parts of this trail can be driven today through states like Tennessee, Arkansas, and Oklahoma. It serves as a sobering reminder of America’s past, with historical sites and memorials along the way.
