Motorcycle Bucket List: Route 66, Chicago to Santa Monica

To me, “Route 66” has always been a magical term. Especially for anyone who still has a bit of their brain stuck in the 1950s (yes, that would be me πŸ™‚ ), that road is almost sure to be part of the memory. I’ve driven some small sections of it in California, but seeing the whole route, with lots of time to soak it all in, is still on my Bucket List. And it’s a road that may be best suited to my motorcycle. Kiara Wilson at Motorcycle House and I have been chatting about great rides and gear, and she offered to write a guest blog about Route 66 for ExploreNorth.

Every once in a while, a rider is called to the road like few other duties. Of course it’s involuntary, but the sheer passion and enjoyment of riding causes a burning desire to seek the open road. While afternoon trips and day rides can wane that burning desire every now and then, a multi-day trip is needed on the bike. For a select few motorcycle enthusiasts, the challenge of Route 66 is a calling that simply must be taken. Starting in Chicago and ending in Santa Monica, Route 66 is often referred to as Main Street of America for the amount of land area it covers: 2,451 miles, to be exact.

Riding Route 66

While the history of Route 66 is rich and lengthy, the proposal for the name and the exact route came about in the mid-1920s. Because the country needed a sustainable route that allowed travelers to move easily from the Midwest to the West, Route 66 was conceived to connect other major highway systems in order to create a vein-like system of roads. Today, Route 66 connects a seemingly infinite amount of public roads together in order to give motorists any number of opportunities to exit and explore the neighboring communities. The popularity of Route 66 boomed in the ’30s and ’40s as ownership of cars exploded. Many towns flourished along this highway, and new economies were born. But as changes in numbering and road construction came in the ’50s, Route 66 began to decline and many of these towns diminished. Today, Route 66 is still a staple among travelers, and it’s become an iconic route for American culture, as have some others.

Route 66

And then there was the motorcycle. Throughout the highway’s life, motorcycles have been a popular method of transportation. And why not? As it’s one of the longest stretches of a single-named road in the country, Route 66 covers so many various terrains and states; it’s hard not to accept the challenge of the ride. From flat, never-ending plains to twisting mountain roads, motorcyclists will get all the thrills and relaxation packed into one trip. Because Route 66 covers so much land in so many different counties, maintenance varies upon location. Riders should be aware that flat, even surfaces can quickly turn into bumpy roadways.

Route 66

Because the duration of the Route 66 ride is so long and covers so many different areas, riders will experience a multitude of different climates during their journey. Regardless of whether you head out in Summer or Winter, riders should understand that packing heavy is almost a must. You’ll experience both windy and calm conditions, and rain will surely present itself somewhere along the way. While First’s Buffalo Nickel jacket or similar light attire might seem comfortable for one stretch of the highway, rougher, colder areas might require something a bit heavier. In this case, pack away multiple jackets – River Road has one for just about any occasion.

Route 66

Route 66 simply must be experienced in order to appreciate its worth to American culture and the U.S. highway system. You’ll see majestic mountains and iconic towns along your journey, and there’s no replacing the memories you’ll have for years to come. Remember to set aside some serious traveling time, because Route 66 cannot be rushed.

Yeah, Route 66 is a ride that needs to be done! πŸ™‚
Alaska Highway Kilometer 1566
For loads of information about it, visit Historic Route 66.
Route 66 map


Motorcycle Bucket List: Route 66, Chicago to Santa Monica — 5 Comments

  1. It’s very accidental to find your website on the internet. I drove to Tuktoyaktuk from Vancouver with my friends this end of March. We drove along the No. 97 Hwy, Alaska Hwy, Klondike Hwy and Dempster Hwy. It’s a amazing trip. If I find your website earlier, I can get more information . So very thank-you for the useful information and beautiful pictures on your website and make me remember the scenery on the way.

    I have a question want to consult you. When I and my friends came to the North areas, our phones have no service in most of the cities and towns except Whitehorse. But the locals can use their telephones in the little town just like Teslin even Tuktoyaktuk. We are puzzled which communication they used. As you known , the satellite phone is a little expensive and we need contract with our family and friends. What’s your suggest about the communication and how you contract with your family?I’m looking forward your reply.

    Route 66 is another my dream road in North America. I will stay focused on your website.

    • Hi Cooky. It’s always nice to hear that my articles have brought back some good memories of past trips. As you discovered, we have extremely limited cell coverage. In most of the smaller Yukon and NWT communities, only older style CDMA phones will work – Smartphones only work in Whitehorse, Haines Junction, Watson Lake, and Dawson City. I have OnStar in my car, and even they were surprised that it seldom works here, after promising me that it works everywhere (I knew that it wouldn’t but bought it anyway – it does work in the communities).

  2. Hey there. My father has given me the chore of finding some really good information for motorcyclist wanting to travel Route 66. He turned 66 this year and like you it is on his bucket list to travel Route 66 while he is 66 from beginning to end. He plans to maybe take a month to do the drive. He has been name Ironbutt 3 years in a row; so I have no doubt he will do it and enjoy it! He is riding his Harley and loves taken the beaten path. He said and I quote, “I won’t take one interstate all the way there!” lol. He is old school and has finally figured out his iphone, but the internet might as well be Mars for him. What do you suggest I start looking for. I plan on buying him some books geared toward the motorcyclist traveling Route 66 but there is so many on here, I’m lost. Any help or information you could share would be greatly appreciated πŸ™‚