EL RENO, OKLAHOMA - JUNE 04: A red Chevrolet Biscayne cruises down historic Route 66 on June 04, 2026 in El Reno, Oklahoma. Known as the “Mother Road,” Route 66 linked small towns and major cities across the United States in its heyday from the 1930s through the 1960s. In its 100th year, it remains a symbol of Americana, preserved through vintage landmarks, roadside attractions, and local businesses. (Photo by Heather Diehl/Getty Images)

Route 66 turns 100 this year. It’s considered America’s most nostalgic road trip. With wide open road, sunsets that fill the whole sky, dirt-kissed Chevy trucks, and revving motorcycles. But Route 66 started out as a muddy road to nowhere. Today on the show, we’ll meet a league of gilded-age bicyclists, a ragtag gang of cross-country runners, and the very stubborn highway commissioner who turned it into the “Main Street of America.”

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