Cruising Route 66 in a 1957 Pontiac Star Chief

September 19, 2026 jasonspiess The Crude Life 0

The couple hadn’t planned on stopping long. But the car did the talking before they did — a 1957 Pontiac Star Chief, polished enough to pull eyes off the highway and onto the chrome.

“Is this your vehicle?” I asked.

“Yes,” the driver said.

“What kind is it?”

“A ‘57 Pontiac Star Chief.”

They were from Minnesota — St. Paul.

They’re doing the whole route — but “backward”. Santa Monica Pier first, Chicago last. Almost a slip of the tongue gave it away: “We’re heading to California — I mean, sorry, Chicago.”

There’s a reason for the direction, and the timing. They want to roll into Pontiac, Illinois — a name that shares more than a passing resemblance to the car in their garage — for the town’s 100th anniversary, marked because the Pontiac car brand, discontinued years ago, would have hit that milestone if it were still on the road.

A Pontiac vehicle, in Pontiac, for the Pontiac centennial. It’s the kind of coincidence Route 66 seems to manufacture on a regular basis.

It’s one more look at the Star Chief before they pulled back onto the highway. Fifty-seven. Still turning heads on Route 66.

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jasonspiess
Author: jasonspiess

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