A Father and Son Rediscover America on Route 66

In the lead-up to the 100th anniversary of the establishment of Route 66—the iconic 2,448-mile historic highway from Chicago to Santa Monica- my 13-year-old son Henry and I will strike out to discover, once and for all: What’s the deal with Route 66 anyway?

Forty years after being decommissioned and stripped from the maps, how—and why—has Route 66 retained its vaunted title as “America’s Highway” in the minds of millions of Americans? And what darkness lies behind the alluring glow of the route’s neon signs?

In 2016, then-six-year-old Henry and I struck out on a different journey: retracing the Oregon Trail in search of “discovering America” for a book called Go West Young Man. Seven years later, we’re going to try it again. Only this time, he’s a teenager. And I’m a dad with no idea how to parent a teenager. Spending hours together in a car is neither of our first choices for how to spend ten days. But if Route 66 can fulfill its promise to show us where the past meets the pavement—and point us forward, too—then perhaps this trip will be just what we need to reconnect with ourselves and our country.

What was lost when Americans stopped pulling over to the side of the road? And what can a father and his Gen Z teenager learn about America while traveling Route 66 today?

Join us on our journey along “The Mother Road.”

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