Itinerary suggestions made with assistance of Emily Heeb.

The iconic Route 66 has captivated America since its earliest days. As motor travel became increasingly affordable, highways became beacons that stirred the imagination of Americans. During its heyday, this 2,400 mile stretch connected Chicago with Los Angeles; the Midwest to the Pacific Coast. 

History of Route 66

The design of Route 66 is an interesting story. With the rise of the automobile in the Roaring Twenties, governments were called upon to build highways. Determining a route was of significant geographic, economic, public and political interest. In the case of 66, planners lobbied decision makers to build a highway that would pass through towns and cities, rather than circumvent them. Route 66 would ultimately thread together urban centres and rural towns, some of which had never been exposed to national throughfare. This earned the highway the monikers 'Main Street of America' and 'Mother Road'. It took five years to complete Route 66 with the sweat equity of thousands of young workers who had sought employment during the recession-plagued Dirty Thirties. The last miles of Route 66 were paved in 1938, but by this time the rubber and steel that had been used to manufacture cars had been rationed for WWII military efforts. Following the war, Americans were increasingly mobile and a period of prosperity ensued; road tripping Route 66 in its entirety became a cultural phenomenon.  

The Original Route 66

route 66
Credit: By Xnatedawgx (Own work), via Wikimedia Commons

End of an Era

While public affinity for Route 66 never truly dissipated, demand grew for major interstates that offered more direct routes and quicker transit. Furthermore, President Eisenhower admired the efficiency of Germany's nationwide Autobahn. By the 1970s four-lane expressways bypassed nearly all of Route 66. Decommissioned, parts of it became dilapidated or disappeared altogether. The interest in preserving Route 66 fell to not-for-profit state associations. It wasn't until the early 1990s that sections of the route achieved historic byway status, and those iconic official route markers were posted.  

The Nostalgia

Route 66 teepee

So how is it that a decommissioned stretch of asphalt still thrives in American and Canadian consciousness? The answer is simple, it's the nostalgia of a bygone era. Route 66 symbolizes an age of discovery, when mobile America hit the road and drove deep into her heartland. The drive embodied a sense of optimism and prosperity after 15 years of economic struggle and an international conflict. Route 66 pays homage to a time well before the rise of generic. None of the diners, motels or boutiques belonged to franchises. The curio shops and neon signage that dotted the highway were unique and novel. Perhaps most intriguing today is the nostalgia of pre-internet travel. It was a time when interactive maps weren't held in the palms of our hands, when roadside assistance was limited to next vehicle travelling along Mother Road; and the best travel advice was delivered via word of mouth. 


Trip Planning

While determined road trippers can complete the Oklahoma portion in a day, rushing through would defeat the purpose. (We doubt those readers would have made it this far through the article! Glad to know we're in good company.) There are so many reasons to explore this state at a leisurely pace. Our own reasons? We want to order a cup of dark coffee and eggs over easy, in an old-fashioned diner from a gal named Alice. We want to pull into the porte-cochere of a single storey motel that sits below a welcoming neon sign. We want to make roadside diversions on a whim to inspect wonderfully weird attractions, and peruse curiosities in eclectic emporiums.

Led by this sentimental travel style we've created an itinerary that spans three full days. This should allow Canadians flying to Oklahoma to plan a getaway in the space of a week, and leisurely cross-country road trippers not too long a time in a single state.  

Trip Notes

  • This itinerary can be completed in either direction (east-west or west to east) 
  • Flying from Canada to Oklahoma and renting a vehicle? Consider accessing Oklahoma from airports in Kansas to avoid back tracking along Route 66. Witchita and Kansas City are just a few hours from the start of our itinerary in Miami, OK.
  • Finish your trip in Sayre and circle back to Oklahoma City to return your rental. On the I-40 West it's just a short two hour ride. If you have more time, head south and depart for home from Dallas-Forth Worth, one of the US's premier airports; an attraction in itself.

Day One

Drive itinerary
: Miami - Claremore
Distance: 101 kilometres


Claremore Motor Inn. It may not be the most historic motel on our itinerary but it certainly offers comfort and value. Claremore Motor Inn sits directly on Route 66 and is perfectly positioned at the end of the first leg of our journey. Plus, it still falls under the motor inn moniker. 


Waylan's Ku-Ku Burger. Once a national chain, Waylan's Ku-Ku Burger in Miami is the last location still standing. And boy is it a taste of Mother Road nostalgia. For a classic meal order a giant cheeseburger and Ku-Ku fries. The food is cooked fresh to order, so while you wait for the order to come up, take a moment to admire the vintage photos that decorate the interior.  If you're worrying about missing the restaurant, don't fret. A large, yellow and green sign in the shape of a bird house is a neon beacon to the hungry. 

Waylan's Ku-Ku Burger.


When we think classic Americana, we think motorcycles. While there are many motorcycle museums along Route 66, the Vintage Iron Motorcycle Museum is arguably the best. However, we issue the warning that a visit may convert conventional car folk to road religion. Admire a collection of vintage helmets, a 1917 Harley Davidson and a rare 1919 GCS. The museum also pays homage to Evel Knievel, America's most daring motorcycle son. 

vintage motorcycle museum oklahoma route 66

While passing through Foyil, don't miss Totem Pole Park. This park is one of the many quirky attractions that have made Route 66 world-famous. In 1937 retired craftsman Ed Galloway started to make folk art totem poles as a tribute to Native Americans. The park also houses a museum, domiciled in an eleven-sided structure inspired by a Navajo hogan. Totem Pole Park admission is free but the park operates limited daytime hours. Click here for visitor information

totem pole park oklahoma


Day Two

Drive itinerary
: Claremore - Oklahoma City
Distance:  215 kilometres


Skyliner Motel. The Skyliner Motel in Stroud is one of the true jewels of the road. It is everything one would expect from a Route 66 motel. With a massive neon sign out front and all the kitschy trappings of the 1970s, Skyliner provides a comfortable night in the past.

skyliner hotel stroud


POPS: Soda Ranch. No trip down Route 66 is complete without stopping in at POPS in Arcadia. Although it is one of the route's more recent additions, it has already become a beloved institution. In traditional Route 66 style, a 20-metre tall soda bottle marks its location. Admire a 12,000 bottle collection of pop bottles and sample a few of the 600 soda flavours on hand. Feeling peckish? Opt for a hand-dipped milkshake and burger in the old fashion diner. 

POPS soda ranch


Chandler Route 66 Interpretive Centre. Route 66 is home to an inordinate number of museums dedicated to itself, but one of the most unique is located in Chandler. The Chandler Route 66 Interpretive Center provides the history of the route in a sensory experience, combining sight and sound. Housed within an old sandstone armoury, visitors can sit back and watch firsthand video that chronicles the full history of Route 66. Learn about attractions past and present. You may even be inspired to drive right through to California. 

Blue Whale. What's big, blue and looks great in a baseball cap? It can only be the iconic blue whale landmark in the town of Catoosa. The 24 metre long and 6 metre high whale lies next to a swimming hole favoured by the grandchildren of its architect Hugh S. Davis. Today, Route 66 travellers seek out the roadside oddity to jump from its tale into the water, or slide down a fin. The Blue Whale is also a fine place for a picnic. 

blue whale catoosa


Day Three

Drive itinerary
: Oklahoma City - Elk City
Distance: 180 kilometres


Flamingo Inn. Located just off of Route 66, Flamingo Inn is clean, comfortable and spacious. It offers great room rates and receives favourable reviews on travel websites. Plus, we're all for independently owned accommodation along the Mother Road. 


Oklahoma Route 66 Museum. Before leaving Oklahoma on Route 66, pay a visit to the Oklahoma Route 66 Museum in Clinton. If the classic neon Route 66 sign doesn't draw you in, the museum's world's largest curio cabinet should. The cabinet contains a unique collection of artifacts found along the route. From vintage product packaging to antique lamps, the cabinet is very much a time capsule of the era. 

Oklahoma Route 66 Museum


Lucille's Roadhouse. For a real taste of old Route 66, visitors should start the last day of their trip at Lucille's Service Station and Roadhouse in Weatherford. During its heyday, service stations seemed to pop up overnight. While the traffic has thinned a bit, Lucille's has been catering to road travellers since 1929. This place is truly a tribute to a bygone era. It features vintage gas pumps, a museum to its history and a 1950s style diner. The menu showcases American favourites, from hamburgers to gravy-smothered chicken-fried steak.

Has nostalgia ever inspired you to travel?
Have you driven Oklahoma's Route 66? 

We want to know! Leave us a comment below. 

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