Travelling one of the United States’ earliest and best-known cross country roads.

Being from the place that Route 66 began – Chicago, Illinois, I have often been along regional sections of what is colloquially called the “main street of America.”

This name for the highway is not just cute; the route was one of the earliest parts of the US Highway System, and followed the same path of early “auto trails” that took migrants and adventurers from Chicago all the way to Los Angeles, California. Today, a Route 66 trip should rightfully be done in a minimum of a few weeks, if not months, to take in the grand scenery and the many historic photo stops and eateries along the way. I joined with a few friends for good company on the trip, but some people may prefer to go it alone.

This is not a complete list of all of the states that Route 66 goes through, but it covers most of them.

My Kind of Town

Starting in Chicago is a great way to begin a trip across the Western part of the country. The city boasts myriad cultural delights, man-made wonders and lots to do. Take a double-decker bus tour through downtown Chicago and its suburbs, or a walking tour or Chicago River boat tour if you’re there in warmer weather.

The “Gold Coast” from the river north has boundless shopping centres of great fame and endless stock. There are too many stores to mention here, but kids will love the Lego Store, Jil Sander will thrill both men and women who love superb clothes, and you can easily spend a day in the famous Water Tower, where you’ll find dozens of world-famous stores.

Like Italian food? Then hit Gino’s East for some of Chicago’s famous deep dish pizza or try famous Spiaggia, which will have you talking Italian for a long time. Lou Mitchell’s, Chicago’s longest running breakfast restaurant, is also a must. In fact just about every culture’s food is available in Chicago at every turn.

To “officially” start our trip, we walked south of the River, past the famous Wrigley Building and many original skyscrapers that are still Chicago and US treasures. This is where you’ll find the Art Institute of Chicago, the wondrous Natural History Museum and Shedd Aquarium, both along the edge of always-stunning Lake Michigan.

This site is inches from Route 66’s start at Michigan Avenue and Adams Street, where you’ll see the famous sign posted proudly. From there we head out of Chicago and passed along Ogden Avenue in North Lawndale, and through the city-towns of Cicero and Berwyn, then along Joliet Road in Lyons, McCook and through Indian Head Park and Burr Ridge. You’ll actually be following Interstate 55 on current-day maps, as many parts of Route 66 have been decommissioned over the years.

Presidents and Pedestals

We entered Springfield, beloved American President Abraham Lincoln’s hometown (for much of his life, and where he met his wife), to coincide with September’s famous Route 66 Mother Road Festival. This melding of vintage cars, trucks and motorcycles creates a noisy, shined-up mix of vehicles, live music and crafts with food vendors stretching for blocks.

In honour of the theme I slipped off to explore Shea’s Gas Station Museum, where Bill Shea has long told stories to visitors about the massive collection of gas station memorabilia he’s collected, and plenty of tales about life along Route 66, accompanied by countless photos. I was fascinated by the guestbook, graced with signatures of visitors from around the globe.

The real kicker though was a simply superb “hot dog on a stick” meal at the Cozy Dog Drive In – the ‘stick-meal’ invented in 1946 by Ed Waldmire, whose family still runs the eatery – and sitting in the car to watch a movie at the Route 66 Twin Drive In Theatre with fresh popcorn included. (The theatre will reopen in April 2014.)

Hills and Caves

The Ozark Highlands of southern Missouri are some of the loveliest hills along this old route, especially with a blaze of fall foliage. Though you can now travel along the I-44 freeway, we stuck mainly to the slower, nearby roadway of fame.

A highlight that remains from older days of Route 66 is the Meramec Caverns. This wide-ranging 3.6-mile (7.4-km) underground limestone cave network is truly amazing. Dubbed “Jesse James Hideout”, a tour of the caves includes stunning walks through colourfully lit caverns brimming with stalactites and stalagmites.

Of course, more ‘up-there’ and updated, is the St. Louis Gateway Arch, for nosebleed-inducing views and awe-inspiring pics. I was actually more into the Vacuum Cleaner Museum in St. James, however, while the fun gang at Johnnie’s Bar in the same town served up superior hamburgers, and folks of all stripes, including lots of bikers on the Route 66 ride, were great to hang out with.

Old Oklahoma

The US National Register of Historic Places includes several notable Route 66 stops worth visiting and photographing. Of course, we couldn’t resist stopping off at a number of these to make for slide shows of the trips afterwards.

After visiting Ed Galloway’s Totem Pole Park in Foyil, it seemed only natural to want to see the countering circular structure of fame, Arcadia’s Round Barn. This massive community-gathering place was rebuilt by 1992, and amazes many as one of America’s few round barns.

Another Oklahoma highlight was POPS restaurant and soda store, where you can get hundreds of flavours of soda, but you’ll be more stunned by the 66-foot tall soda bottle just along the route of the same number. This sort of shameless hucksterism is what the Route 66 vibe is all about.

Festive Pursuits

Home to many artists and artisans of fame, New Mexico happily shows off some of its Route 66 memories.  Santa Fe’s Silver Saddle Hotel was worth a stay, just to get the flavour of cowboy, cowgirl themes that were part of the Great West tone of the route’s heyday here.

If you time the trip for September, you also get the extra treat of being floored in the desert by the Albuquerque International Balloon Fiesta. The pre-dawn ceremonies are well worth seeing, but they are only a tease to the breath-taking take-off of hundreds of multi-hued, differently designed hot air balloons that literally blot out the sky. Not a feature in the route’s early days, this is nevertheless a modern event worth experiencing along the way.

Waving Arizona

Flagstaff, Arizona is a remarkable place, thanks to its sunny people that match the warm, friendly climate. Check out the checker-tiled floor at Mr D’z Route 66 Diner for a friendly flashback to earlier times, when service with a smile was the norm.

While we didn’t time this trip to catch the Fun Run May 1 celebration of vintage cars, there were several parked out front. I love talking to the owners. The care and appreciation they have for the automobile is always a fascinating treat.

I’d also suggest a trip to Winslow – a little off the route’s line – to see Meteor Crater. This almost one-mile-wide, 2.4-mile circumference, 550-foot-deep hole makes as much of an impact on you as the original meteor did on the earth. If you watch the movie in the special theatre, you’ll also experience the whole event in rollicking 3-D.

California Dreaming

I can’t even begin to fully list how many cool places there are to visit around the final leg of Route 66 in California. The Bottle Tree Farm in Oro Grande is stunningly photogenic, the original McDonald’s Museum in San Bernardino beckons burger and fries lovers and the Chinatown there is like no other in any city, except maybe one in China.

On the road you are sure to be overwhelmed by all the kitschy collectibles (including a whole multi-coloured bus) at various Barney’s Beanery bar and restaurant locations (West Hollywood, Pasadena, Burbank, Santa Monica, Westwood and Redondo Beach). Hubcaps, license plates, old car seat booths, old newspaper clippings, games, bumper stickers and signage festoon each place. All this and enough types of beer (over 200) and menu items (700-plus) to make anyone happy.

The connection to classic American cars is always apparent along Route 66, just as it was during the roadway’s most-used years. Many old, but incredibly well maintained cars are seen all the time here; the dry desert air of the Southwestern states helps to preserve them. I was treated, by request of course, to a roaring flash-by of a half-dozen of these beauties, and I have the home video to prove it… with volume galore!

Following Route 66 is like taking a trip through time, tinged with sights and symbols of the country’s past. It’s also a beautiful journey, so I recommend those on a slow track to take this pleasure-filled adventure; you’ll long remember its many sights, sounds and tastes.


Most Americans and foreigners only know Route 66 thanks to the famous 1946 Bobby Troupe song, “(Get Your Kicks on) Route 66,” sung by Nat King Cole. Here are a few travel facts that take you beyond the melody.

  • Route 66 is 2,448 miles (3,940 km) long. First established in 1926, the roadway was sign-posted the following year.
  • It was familiarly called the “Will Rogers Highway” after that famous actor and public figure greeted early travellers in California upon arrival there. A plaque dedicating the route to Rogers still exists in Santa Monica, California, as does one in Galena, Kansas.
  • The Route’s nickname, “The Mother Road,” comes from American author John Steinbeck’s famous book, “The Grapes of Wrath”. The book was made into a movie directed by famed film maker John Ford.
  • Preservation groups have attempted to retain and even landmark the numerous neon signs and old hotels that still exist along Route 66 in many states. Many communities proudly paint the road’s name and number right onto the route’s surface to make it stand out.
  • In 1999, President Bill Clinton created the National Route 66 Preservation Bill, which created USD$10 million in matching fund grants to restore and preserve many historic sites and features along the fabled route.
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Jim Grubman
Jim Grubman has lived more lives than the average cat, though he's hoping his two Flame-Point Himalayans beat him. He has written and edited many things, including cookbooks (he's a qualified chef), and he has even saved lives as a dialysis technician among a long list of medical and other jobs. For fun, he travels, writes about it, and sails as close to the Southern Seas as a sane man dare try.