LILLEY: Slow it down and take a breath while cruising Route 66 in Arizona

Take a slow and nostalgic drive from Winslow to Oatman on America’s Mother Road

Few roads have the folklore, mythology and nostalgia of Route 66. Sure, there’s the Pacific Coast Highway in California, there is the autobahn in Germany, but Route 66 has a special place in the hearts and imaginations of travellers around the world.

America’s Mother Road, as she is called, is about to celebrate its 100th anniversary in 2026, an event that will draw backpackers, vagabonds, motorcycle enthusiasts and vintage car geeks from around the world. If Route 66 is on your bucket list, plan on being there for the centenary, it doesn’t disappoint.

Originally running from Chicago to Los Angeles, most of the roadway was replaced by the Interstate system beginning in the 1960s and the last stretch of Route 66 was decertified in 1985. Thanks to the work of local activists, town and city councils, and plenty of nostalgia buffs, there are stretches of the old route preserved to this day.

Yes, you can still get your kicks on Route 66, especially in Arizona, the state that is home to the longest stretch of preserved highway. From small forgotten towns like Oatman to cities that still take Interstate traffic like Kingman to Winslow, Arizona where you can stand on a corner, the Route 66 experience in The Copper State is first class.

Slow it down…

The best advice I can give for someone looking to tour along Route 66 is to set aside your GPS or Google Maps – they will direct you to the Interstate.

I’d also say you need to take your time to soak up the scenery, the majesty of Arizona, the desert, the mountains. Get up early to watch and photograph the sunrise, make sure you are outside for sunsets as well because those parts of the day out in the desert are just spectacular.

Where to go?

Phoenix offers direct flights from several major Canadian cities; Porter even recently began offering direct flights from Toronto at a good cost. From there you can choose to head north to Winslow and drive west like so many did in the past or follow modern highways up through to Oatman – maybe with a stop at Lake Havasu – and drive west.

The Standin' On the Corner Park in Winslow, Arizona
The Standin’ On the Corner Park in Winslow, Arizona memorializes the hit song Take it Easy written by Jackson Browne and Glenn Frey. BRIAN LILLEY/TORONTO SUN

Winslow

Winslow fully embraces the vibe of the hit song Take it Easy co-written by Jackson Browne and Eagles founder Glenn Frey. In the middle of their downtown strip sits Standin’ On the Corner park with a statue of Frey and a statue that looks like Browne, but locals insist is not.

And of course there is a flatbed truck slowing down to take a look at you.

From there, head west to Williams, perhaps with a stop in Flagstaff, the hip college town nestled in the mountains where many athletes come to train due to the high altitude.

La Posada Hotel
La Posada Hotel in Winslow, Arizona features an amazing southwest-inspired adobe design and beautiful gardens. BRIAN LILLEY/TORONTO SUN

Williams

Williams, Arizona
In Williams, Arizona, some people take their horse to the bar. Route 66 in Arizona BRIAN LILLEY/TORONTO SUN

When Interstate 40 took traffic off of Route 66 near Seligman in September 1978, Angel Delgadillo, who had been born and raised in this tiny town, immediately saw a drop in traffic and business. His barbershop, like so many in this town that relied on Route 66 and the railway to survive, wouldn’t stay open if things remained this way.

Delgadillo formed the Historic Route 66 Association of Arizona and successfully lobbied the Arizona State Legislature to preserve Route 66 as an historic highway. After that, California, New Mexico, Texas, Oklahoma, Kansas, Missouri, and Illinois all followed suit in preserving many of the remaining parts of the highway.

Today, Angel’s Barbershop is a tourist destination, Angel gave up cutting hair a few years ago at age 95 and he’s turned the business into a gift shop for Route 66 wear.

The jail in Kingman
At the jail in Kingman, they have some strict rules. BRIAN LILLEY/TORONTO SUN

Kingman

The classic car show during their Route 66 festival is an amazing adventure, especially paired with the growing showing of vintage trailers and RVs. Kingman is also home to The Route 66 Museum and a growing collection of EVs in their electric car museum, it’s definitely worth a pitstop.

The town has also recently undergone a revitalization of downtown with new streetscaping and new businesses including a couple of craft brew pubs and lots of great restaurants. Walk about the town using a self-guided audio walking tour and when you get to the jail look for my favourite sign.

“It is unlawful to communicate with the prisoners with permission from the Sherriff’s Office,” the sign posted outside the old jail reads.

You will get your kicks and more driving along the Sidewinder outside of Oatman, Arizona. BRIAN LILLEY/TORONTO SUN
You will get your kicks and more driving along the Sidewinder outside of Oatman, Arizona. BRIAN LILLEY/TORONTO SUN

For the brave of heart, Sitgreaves Pass will take you on a winding path to the town of Oatman. The winding road, often without guardrails, is harrowing but the views are spectacular.

There were definitely times I was nervous on this long and winding road, and was wondering if I was overreacting until we hit the giftshop at the end selling gear declaring, “I survived The Sidewinder!” This stretch of the road is a favourite of the many motorcyclists and daredevils.

A wild burro on the side of Route 66 just outside of Oatman,
A wild burro on the side of Route 66 just outside of Oatman, Arizona. BRIAN LILLEY/TORONTO SUN

In addition to taking your time and making sure you get photos of the sunrise and sunset, make sure you take advantage of one of the great parts of driving Route 66 – it’s off the beaten track. Give up on fast food and chain restaurants and embrace the slow and local when it is time for a bite.

From great local hamburger joints to southwest BBQ, there are so many great flavours, fantastic meals and interesting experiences that you won’t find in the chain place at the Interstate rest stop.

So, what are you waiting for, go get your kicks on Route 66.

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