There’s something magical about following the tire tracks of history. Since the early days of the automobile, road trips have offered more than just transportation. They’ve been journeys of discovery, connecting travelers to the stories, struggles and triumphs that shaped the nation. You can still travel some legendary routes today, uncovering hidden gems and forgotten chapters of American history.
1. Route 66: The Mother Road
No list of historic American road trips would be complete without Route 66. Established in 1926, this stretch of road connected Chicago to Los Angeles. It became the primary route for Dust Bowl migrants heading west during the Great Depression. Today, while interstates have replaced much of the original route, dedicated sections remain drivable, offering glimpses into midcentury America.
Key stops include Seligman, Arizona, which inspired the town of Radiator Springs in Pixar’s “Cars.” Don’t miss the Cadillac Ranch art installation in Amarillo, Texas, where 10 Cadillacs are buried nose-first in the ground, creating a surreal tribute to American automotive culture.
2. Blue Ridge Parkway: America’s Favorite Drive
Winding through Virginia and North Carolina, the Blue Ridge Parkway originated during the Great Depression as both a scenic drive and a jobs program. Construction began in 1935, connecting Shenandoah National Park to Great Smoky Mountains National Park through some of the most stunning mountain scenery in the eastern U.S.
The parkway showcases Appalachian culture through historic cabins, working gristmills and traditional craft demonstrations. Time your visit for fall to witness spectacular foliage, or come in spring when mountain laurel and rhododendrons bloom. Notable stops include Mabry Mill in Virginia — one of the most photographed spots on the parkway — and the Folk Art Center near Asheville, North Carolina, where you can watch local artisans at work.
3. The Lincoln Highway: Coast-to-Coast Pioneer
The Lincoln Highway holds special significance in automotive history. America’s first transcontinental highway stretched from New York’s Times Square to San Francisco’s Lincoln Park. This revolutionary road represented the dawn of automotive travel in 1913, inspiring adventurous motorists to attempt cross-country journeys that had once seemed impossible.
In Ohio, the highway passed through small towns like Galion, where three of the original four Vagabonds — Ford, Edison and Firestone — stopped in 1923 after attending President Warren G. Harding’s funeral in nearby Marion. The historic Gill House they visited is now open to visitors, offering a sense of connection to these automotive and industry pioneers.
You can still follow portions of the original route, marked by distinctive red, white and blue Lincoln Highway markers. Discover roadside attractions like the world’s largest ketchup bottle in Illinois and exploring historic downtowns that once served weary transcontinental travelers.
4. Pacific Coast Highway: California Dreaming
California’s Highway 1 — particularly between San Francisco and Los Angeles — offers one of the world’s most scenic coastal drives. While not as old as other routes on this list, sections date back to the 1930s, built by convict labor and Civilian Conservation Corps workers who carved the road into cliffsides with hand tools.
The drive showcases California’s diverse landscapes, from the rugged Big Sur coastline to the Spanish missions that dot the landscape. Stop at spots like the Hearst Castle in San Simeon — the opulent estate of newspaper magnate William Randolph Hearst. Explore the artist colony of Carmel-by-the-Sea. Each curve reveals new vistas of crashing waves, redwood forests, and golden hillsides that have inspired countless travelers and artists.
Planning Your Historic Road Trip
Research your chosen route’s history before departing. Understanding the stories behind the road enriches every mile. Pack essentials like paper maps as backup to GPS, a cooler for picnics at scenic overlooks, and a camera to capture iconic landmarks and unexpected discoveries. Most importantly, allow some extra time for spontaneous stops at roadside attractions, local diners and small-town museums, which often hold the most compelling stories.
Respect the communities and heritage sites you visit by following posted guidelines, supporting local businesses and leaving no trace. Remember that many of these routes pass through areas where people live and work. When you pass through, you’re a temporary neighbor.
Start Your Own Journey Through Time
These historic highways offer more than scenic beauty. They’re time machines that can transport you to different eras of the American experience. Whether you want to experience Route 66’s nostalgic Americana or the Lincoln Highway’s pioneering spirit, each route tells a unique story about who older Americans were and what the country has become.
Pack your sense of adventure and hit the road. History is waiting just around the next curve.
Jack Shaw is the senior editor of the men’s lifestyle publication Modded and a freelance writer working professionally since 2018. In this time, Jack has been sharing years’ worth of explorations and the best tips that he’s learned along the way. His works have been featured in Trekaroo, The Travel Magazine, Washington Trails Magazine and more.
