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A Motorcycle & Route 66


A Motorcycle & Route 66

Ben Ashby

They came from foreign lands, they came from distant cities. From Chicago, from New York City, from tiny Connecticut towns, they came from Miami, and they came from Los Angeles all searching for something more, searching for something different. The reality is we live in an overly digital, overly connected world. They came searching for a reprieve from the 24/7 political nightmare, from the 365 biased news overload. They came searching for places that had been untouched, places that meet the morning horizons with zero traces of man or modernity. They came for a motorcycle tour of Route 66 with Los Angeles based motorcycle touring company EagleRider



When I got the call asking if I’d go on a motorcycle tour down Route 66 with a touring company I had several concerns, questions, comments, etc etc. We’ll address those as we go, but for the sake of the beautiful narrative I have in my head lets continue with where I was headed. 

The kids on the trip showed up in their Ubers clad in the standard all black uniforms of the American cities. they brought with them every device short of beepers. Constantly connected to business emails, to Instagramers, to Twitterers, to txting, and weird side projects they were working on. The majority had never been on a motorcycle, and the majority had never been deep into the desert out west. After a brief mixer at the Eagle Rider headquarters they quickly found common ground. Three worked in the same tower off Columbus Circle. One would soon be the other’s boss. The phones slowly were used less and less and real tangible connections were made. The CEO of EagleRider greeted us and welcomed us to what would be our three day tour. He began it all by telling us a motorcycle tour of Route 66 is as American as apple pie. A rite-of-passage that every American must do. EagleRider was the perfect means to make this possible.

EagleRider was founded on the idea of providing motorcycle riders with motorcycle rentals in locations all over the world. You can rent them in a very similar fashion to renting a car at Enterprise or Hertz. EagleRider also offers guided tours of routes all over the world. From short ones like our three day tour of Route 66 from Los Angeles to Las Vegas, to a complete tour of Route 66. EagleRider has locations all over the world. 


After the CEO’s introduction we were fitted in our motorcycle jackets and outfitted in some appropriately themed gear. Indian is one of my favorite bike brands. I quickly went for anything I could find. We packed up and headed out…to basically the best BBQ in L.A…I’ll report back with the name. 

For our tour we were all strangers. We walked into the tour with only one thing in common…a love of words. We would each be responsible for writing our thoughts on the trip. Over dinner we discussed our angles and our plans. We discussed our backgrounds and who our audiences were. I quickly realized I got the lucky job…I have the audience with a love of adventure. 

As worlds connected and the millennials connected the guards and walls of urban dwelling and politics and whatever this weird round the clock negative news world we live in fell away. Moods became lighter and the excitement build for the journey that would begin as the sun rose over the southern California mountains the following morning. 


In the American west the sun rises over the dusty mountains the same as it has for hundreds of years. The march of time has turned coastal deserts of southern California from a vast sandy sea of succulents and cacti to a wild treeless wilderness of horse paths, tiny mining towns, outlaws, and tall tails, to an urban jungle of kids seeking an escape into wanderlust. As the sun rose helmets went on, bikes were mounted, engines were revved, and the tires carrying the millennials were hitting the sun-baked asphalt of Los Angeles. This mornings route would take us high into the mountains towards Palm Springs. The interstates began to fly by as we made our way towards the forgotten highways leading east. 

I’ve already driven from Kentucky to California twice this year in a rented Chevy Malibu. I’ve driven across the US and back in Cadillacs and Toyotas, but I’d never been on the open road on a bike. I’d never felt all the cliches, I’d never felt the wind in my hair. I’d never felt Bette Midler’s wind beneath my wings. The bike ensured a sense of freedom, a sense of abandon, a sense of independence. The wind swept past, the bumps and curves were felt, it was just you and this man made machine. It was you, without a hand to hold a phone, a hand to text, or an ability to talk to those around you. It was just you, your thoughts, the sun, and a reckless spirit of Americana. It was exactly what was needed. 

The cityscapes and the suburbs gave way to orange groves and cattle farms. The ascent up the mountain began. The air grew chilled. The ride slowed down as the curves became tighter and the pack of motorcycles became narrower. Our trip has one main guide and three additional guides that were joining us for the trip. The lead knew all the routes and the curves. He led us the entire trip with a flawless pace. Between the four guides on the tour they complete hundreds of tours a year leading Americans of all ages and tourist across nearly every state in the US. With all of us being from the world of media this was all new territory for us. Hardly any of us had ever been on a bike, much less ridden it through deserts or over mountains. EagleRider specializes in keeping an up to date fleet of bikes and having guides that not only know the roads but also know the details and histories of all the areas they’re visiting. 



We stopped for lunch high in the hills surrounded by pines and cabins. This new landscape seemed an extreme exchange of the landscape we had been immersed in just a few hours ago. The goal of this trip wasn’t to just ride a motorcycle down Route 66…it was about experiencing something different and about being in nature and out of the urban element. The mountains and the mountain themed restaurant were a reminder of that. We all vowed to experience everything as it came and to savor the moments. Basically I am just trying to say we had zero cellphone service as dramatically as possible. Conversations seemed authentic. It is an idea we will be exploring in depth this year—but it seems the idea of living in real life rather than living a digital facade is where we millennials are heading. If you’re looking for a festive way to start that journey—grad and EagleRider bike and head out. 

I am a sucker for Palm Springs. There is something about it being totally lost in time that really speaks to me. Maybe its the desert vibes or the mid century aesthetic, but I am obsessed with the place. The winds outside of town are a true experience for a motorcycle rider, but absolutely worth the thrill. EagleRider has the accommodations perfectly prepared. All luggage follows behind the group of bikes in a sprinter van and everything is unloaded at the hotel. Bikes were parked and we all went inside to freshen up. The digital world was once again available, but few indulged. Being disconnected had become a luxury not worth giving up. 

The next morning I broke away from the group to meet up with a photographer friend to photograph the Desert X house in Palm Springs. This meant I would be picked up by the Jeep that trailed behind the group. It also meant I would be skipping the nearly full day exercising into Joshua Tree National Park. 



We met back up with the group for BBQ in 29 Palms. The rest of our day would be driving through the extremely open roads of Arizona and California. During that afternoon with my Jeep driver I learned a few things about taking a motorcycle tour:

  1. You will be much hotter in black than you will wearing white. In the middle of the summer ditch being stylish for being comfortable.
  2. Stay hydrated. The wind will dry you out. 
  3. Wear every bit of sun screen you can slather on. Don’t forget to coat those fingers and hands well and often
  4. If you want to take a tour but don’t have a motorcycle license grab a three wheeled Slingshot.
  5. Learn the hand signals. 
  6. Know the limits of your bike. When it gets to a certain temp motorcycles (and helicopters) get too hot to operate. 
  7. Put your phone away.
  8. Don’t try to show off. You are absolutely not as good of a driver as you say you are.
  9. When in doubt just ride in the Jeep. 
  10. Always go for the gas station hot dogs. The risk is always worth it.

Our day concludes with a boat tour along the state line and a rest at a casino outside Las Vegas. They tell us we have a long day tomorrow, but refuse to say anything else. 


The hotel sits along the banks of the river in a deep valley. The sun rises slowly yet the heat quickly creeps in. We continue to skirt the Nevada state line. We take routes of Route 66 that seem like a Wiley Coyote cartoon. Roadrunner should be leading our group. Wild donkeys rest alongside the highway and one of the oldest ghost towns in the US sits over the horizon. Oatman, Arizona is a town of legends. A tiny mining town that has been the center of folklore for decades is a nearly preserved reminder of the former America and the newly embraced Chinese made consumption obsessed American tourist. Dew rags and t shirts coat the derelict wooden structures with a vile mix of tacky and trashy. This is the America was have set out to escape. Our bikes quickly become a comforting reminder that we will escape this nightmare as quickly as we entered it. 

Back on the road we are told that we must hurry towards our final surprise of the trip. We are all well bonded and unhappy with the idea that our trip will soon be over. We head across Hoover Dam and head towards the sins of Las Vegas, but first we stop at one of the regional airports where a fleet of helicopters await. 

For many of us this was our first helicopter experience. For all of us this was the perfect ending to our trip. We rose high above the landscape. The desert gave way to the jagged and indescribable beauty of the Grand Canyon. We soared over the walls and the Colorado river. We had final conversations over headsets and we lamented on the fact that the depths and wonders below would soon give way for a rude reality that our overly digital overly connected lived await. 

EagleRider is a company that was founded on the idea of giving people the freedom of the road and the ability to experience America. Eagle Rider has since provided countless people of all ages with the ability to escape this absurdly negative world. It affords its riders with the ability to head towards an America and a reality that is void of connection. It affords its riders the ability to find tangible connection with strangers, with the sun, with the road, with the time forgotten landscapes or America, and it allows its rides to find a connection with themselves that we millennials are in desperate need of. 

We, the seven millennials were all strangers from foreign lands seeking an experience, and escape, and a connection with each other. We left as seven new found friends with a shared experience and a shared appreciation for a life less modern.