13 Essential US Historical Journeys for Every American

4. Route 66

Nicknamed the “Mother Road,” Route 66 has symbolized freedom, reinvention, and the open road for generations of Americans. Stretching nearly 2,400 miles from Chicago to the storied Santa Monica Pier, this historic route is studded with quirky roadside attractions, classic neon signs, vintage motels, and iconic diners. Travelers often revel in the nostalgia and community spirit found in towns along the way, joining a living parade of road trippers that numbers more than 200,000 each year (NPS, 2023). Preservation efforts by the Historic Route 66 Association ensure that travelers can discover murals, museums, and original stretches of desert highway long after the interstate system bypassed these towns. Whether you’re after legendary Americana, a taste of mid-20th-century pop culture, or just a truly epic cross-country drive, Route 66 delivers adventure at every turn—with rich layers of history hiding behind every carhop window and gas pump.