Every region has its iconic road trip. In Mississippi, the Natchez Trace leads north to Tennessee. In Colorado, the Million Dollar Highway threads the San Juan Skyway. Landmarks of American history sit within four hours of nearly every front door, and 2026 is the year to take advantage of that.
The Mother Road (aka Route 66) turns 100 on November 11, and America hits its 250th birthday on July 4. The coinciding anniversaries are bringing renewed attention to the American road trip—and you don’t have to plan some sprawling four-state route to participate. Consider a regional loop within a gas tank or two of home that keeps an introverted teenager, a curious 9-year-old, the parents, and their parents back for Sunday dinner. No matter how far you’re going, here’s how to prep so the trip is the thing everybody remembers, not the logistics.
