Finding American Icons in the Midwest

Route 66 slides past famous prisons, forgotten drive-ins and unique local landmarks on its way through the heartland.

Photograph by David Guttenfelder
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The "Gateway Arch" in St. Louis, Missouri symbolizes a time when it was one of the most westward cities in the United States. The Arch stands tall along the Mississippi River and visitors can take a tram ride up 630 feet for a panoramic view of the skyline.
Photograph by David Guttenfelder

The sun-blasted streets stood empty when we pulled up to Joliet, nobody in sight but a lowrider club from Michigan. shooting photos of a ’58 Bel Air. The lowriders had set up a photo shoot outside the storied prison, posing a ’58 Bel Air and a half-dressed model against the backdrop of the limestone fortress. When they saw us heading for the gate, they gawked. “You’re going inside?”

We were going inside. Into Joliet Correctional Center, the prison immortalized by Memphis Minnie, Jack Kerouac and The Blues Brothers; the place that locked up convicts for nearly 150 years, so long its name became shorthand for crime and punishment.

The prison has been shuttered and abandoned since the last inmates left in 2002. Only teenagers, vandals, and the occasional arsonist have sneaked past the razor wire and rusting fences. Now local officials unlocked the padlocks and led us into the shadowy rooms of the warden’s residence.

We’d come south that morning from Chicago on what’s left of Route 66, starting our slow ride to Santa Monica to explore the landmarks and stories of the Mother Road. Joliet prison was the first American icon we found.

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The start of the historic Route 66 is marked by an adorned sign in Chicago, Illinois. Here you can also find the famous Willis Tower, and close by, the Old Joliet prision, where the first inmates arrived in May 1858.

“This building is not really—” Gregory Peerbolte, executive director of the Joliet historical museum, swung his flashlight over the walls. “I don’t want to say unsafe, but…”

We paced dank cellblocks where peeling strips of paint hung like a pale vines, then finally emerged onto a vast prison yard choked by weeds and chiming with cicadas. The entire place had the feeling of suspension, as if one day everybody – inmates and wardens alike – simply got up and walked out.

Joliet’s first impulse, Peerbolte said, was to shed the stigma of a prison town. Only recently has the city begun to embrace its notorious landmark with all its nuance and dark fascination. The city hopes to open the prison for public tours in coming months, capitalizing on the flow of tourists down Route 66.

“It’s something the community can be proud of,” Peerbolte said. “It’s part of our story. Is it challenging to present this? Absolutely.”

Light is getting soft. Night is coming. It’s time to keep driving down through Illinois. We plan our stops, but there are so many distractions in between. The murals of Pontiac. The world’s largest covered wagon, the sober halls of Lincoln’s tomb, and the birthplace of the deep-fried corn dog. You can contemplate the true nature of bunnies – and the many shades of American hustle – at the gloriously senseless roadside attraction known as Henry’s Rabbit Ranch. You have to see what you can at every stop, because it’s always time to keep moving down the road.

On a sultry Friday night at the Sky View Drive-In in Litchfield, Ill, families cruised onto the field hours before opening credits rolled. They lugged blankets and chairs and coolers the size of coffee tables; parked on the scabby grass and tailgated while waiting for daylight to fade.

In the shadow of the screen children raced through tag and football, their voices carrying over the corn fields. The grass had been recently cut and the soft dying piles washed around their sneakers. It was a scene out of another age, from a summer that existed before everybody carried a screen in their pocket. Not too far away in Mount Olive, families celebrated the Fourth of July outside in the midwest heat, tasting the sweet humid air while setting off fireworks.

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In Mount Olive, Illinois, a family celebrates the Fourth of July with fireworks on their farm. Mount Olive is just one stop amongst many on the journey along Route 66.

Maybe that’s what people are hunting for along Route 66 – some window into an America that used to be, something they heard about or saw in a movie or half-remember from their own childhood. Maybe something that never existed. Whatever they’re looking for, they’re coming like crazy – flocking here from all over the world and pushing new life and money into communities along the road’s path.

We drove on, over the Mississippi River and past the Gateway Arch of St Louis and on into the hills of Missouri. In the green, cool river flowing by the mouth of Meramec Caverns, families lose a Sunday splashing among the minnows, sunning themselves on beaches of hard rock, dropping from a rope swing into the cool depths. They wade into the river wearing T-shirts, shorts and dresses. These are simple pastimes, cheap picnics, forgotten amusements of the roadside.

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Based in Stanton, Missouri, the Meramec Caverns have attracted Route 66 passerbys since 1935.

Down in the caverns, road trippers take a guided tour of the mind-bending caverns of stalactites, to see where Lassie was filmed and where Jesse James hid from the law and, at last, to watch a patriotic slideshow projected onto a screen of rock.

The highway has its formal sites, but also its flashes of ordinary life. The drivers watch the roadside, and the residents of the roadside stare right back.

Deeper into Missouri, the Pearce family has finally, this summer, gotten around to installing a long-hoped-for swimming pool. The children roll and splash like blonde seals in the water, a plastic flamingo bobbing along.

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A child from the Pearce familiy, based in Springfield, Missouri along Route 66, enjoys a newly built pool and an oversized flamingo on a hot day. Springfield, the capital of Illinois, also dons a number of classic Route 66 hotels and sites.

The adults gather in the shade, pulling on Dr. Peppers and chain smoking Decades, talking about the price of walnut trees and whether the Kansas City Chiefs will be any good this year. They are a logging family; they have lived on this land for generations.

The run of cargo trucks and bikers along Route 66 is the unremarkable soundtrack to their family life. They can tell you about the tourists who pull over to join the family barbecues; about the man who was walking all the way across the country to raise money for cancer.

Their lives are fixed in place, but some kind of American dream is flowing past their porch.

To learn more about our trip along Route 66 with the National Trust for Historic Preservation, follow along the journey HERE.

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