We Love Retro on Route 66

A Blend of quirk and calm on America’s “Mother Road”

by Jessica Blair Howell

There’s a point when the constant chime of email and buzz of the Blackberry just becomes too much. When the clogged interstate has you yearning for true open road, the kind that unfurls before you and begs for just a tick more on the speedometer. It’s less about where you’re headed and much more about the ride, about clearing your head.

But where to go? I’ve got just the place. Go for Americana. You know, blue jeans and apple pie. To me, the kitsch of America’s Main Street—Route 66—does it best. Here, on this time-worn ribbon of pavement stretching about 2,500 miles from Chicago to the tip of the Santa Monica Pier in Los Angeles you can let your citified mind roam back to simpler pleasures.

This is not the kind of getaway you embark on solo. A partner-in-crime is required, be it a Thelma-and-Louise style gal pal or a new man you deem ready for a foolhardy relationship test. You’ll book long hours on the dry and dusty two-lane pavement – originally opened to traffic in 1928 – through small towns, past landmarks labeled “World’s Largest,” and diners touting the same homemade specialties that lured in travelers of a bygone era. (Dieters beware!) Quirky Route 66 is a shot of pure nostalgia.

While your Nav system probably won’t put you on Route 66, you can easily veer on and off today’s wide-laned expressways, finding Route 66 signs that lead you to the old highway. But beware, significant chunks of the original route – including many of those blinking neon signs and peeling billboards – have been demolished or swiped by souvenir-scrounging tourists

When plotting your trip, be sure to note gas station locations. Along some stretches of highway, gas stations can be as far as 100 miles apart. (Don’t even ask about a charging station for a Nissan Leaf.)


Route 66 officially begins in the northeast corner of Illinois, in Chicago, near the intersection of Adams Street and famed Michigan Avenue. Here, amid the skyscrapers of the Midwest, you’ll undoubtedly be distracted by the luxe storefronts of Magnificent Mile. Don’t let the shopping tempt you. You’ll need to leave trunk space for cheesy trinkets you find along the way.

As you drive southwest, you won’t want to miss a peek at the World’s Largest Catsup Bottle in Collinsville, Ill., built in 1949 and preserved today by none other than the Catsup Bottle Preservation Group.

As the odometer rolls over 300 miles, you’ll find yourself in Missouri, where you can hit St. Louis for a picturesque view of the city’s gleaming Gateway Arch, a signal that you’re nearing the best damn dessert in the state—cold, creamy frozen custard—at Ted Drewes Frozen Custard (open seasonally). Try a “concrete,” Ted’s specialty, which blends the famous custard with an overload of sweet toppings.

If you decide the custard is so good that you want to stay overnight to hit Ted’s again in the morning, book a room at the Wagon Wheel Motel, Café and Station in Cuba, Mo., where retro cottage guestrooms feel authentic but are clean and comfortable (suite rates run $110 per night).


Don’t blink or you might miss the short stretch that’s Kansas, a mere 13 miles of well-preserved Route 66 roadway. Soak up the sights as you drive past the abandoned shops and motels.

In Oklahoma, park curbside for a portrait with the legendary Blue Whale in Catoosa and make it your kitschy Facebook profile picture. Originally crafted in the 1970s, this giant whale sculpture is a Route 66 Certified Roadside Attraction that was a surprise anniversary gift for the designer’s wife (cue a look of horror).

In Elk City, Okla., the Route 66 Museum is a collection of memorabilia from six decades of the route’s history. Plus, there are great photos of the Route’s construction, lodging, restaurants, garages and attractions ($5 admission; open Mon-Sat, 9 a.m. – 5 p.m.).

After cruising Oklahoma, you’ll dip into Texas for a few hours, where the “everything’s bigger in Texas” cliche rings true. Famous for its 72 ounce free steak dinner, the Big Texan Steak Ranch in Amarillo challenges all diners to consume its world-famous steak monstrosity in under an hour. Diners who do the deed get refunded the hefty $72.00 menu price. But really, we recommend avoiding the shtick. No, really.

Featured Image: © Dmitry Rogozhin | DepositPhotos.com
Route 66 Begin Photo: © Achim HB | DepositPhotos.com
Catoosa Whale Photo: © The White Pelican
Cadillac Ranch Photo: Flickr.com | © Richie Diesterheft
Barringer Crater Photo: © Larry Bloom
Santa Monica Pier Photo: © PDPhoto.org

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3 Responses to “We Love Retro on Route 66”

  1. Lucille Dolab says:

    Such a fantastic trip!!! We drove what was left of this great road and loved every minute!!! Suggest watching the YouTube version of Bobby Troupe’s tribute song about this American treasure by Natalie Cole and Diana Krall!!!
    Done the way Bobby had meant it to be sung!!! A true jazz classic performed by 2 classy artists!!!

  2. Luka says:

    How long did the drive take in total?

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