Day 0 – Positioning to Chicago

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Route 66 planning, here we go! It’s all considered part of Day 0 – Positioning to Chicago. And “Day 0” actually is several months long. It’s the “run-up” to the actual trip. Day 0 starts with my initial commitment to go until The Driveby Tourist actually sets foot (and wheels) on Route 66 at Adams Street and Michigan Avenue in The Loop in Chicago. As I said, much of the early part of Day 0 is collecting material mostly from Amazon and from internet searches. Actually, Google was my best friend during the planning! Here is a link to a great site about Route 66. My initial stop will be as I cross the state border into Wisconsin. A baby step!

Day 0 - Positioning to Chicago
Welcome to Wisconsin

But I’m getting ahead of myself again. I still have some planning to tell you about before I get here. Seems like you can never do enough planning, right?

Historic Route 66 planning preparation

Books and Google

Doing the planning meant buying and reading books and the various bookmarked sites on the web. My “bible” turned out to be “The EZ66 Guide for Travelers” by Jerry McClanahan. He wrote the book as a series of spiral-bound turn by turn maps. The book includes alternative routes and written narratives regarding the directions. The book also points out key attractions and other things to see. It has a “chapter” for each state. In addition, several other writers took the stage around Jerry’s book. (I met Jerry in Oklahoma but more on that later.) But here’s a link to his website – McJerry66.

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  • Books and Maps for Route 66 planning
    • “The EZ66 Guide for Travelers 4th Edition” by Jerry McClanahan
    • “Route 66 Adventure Handbook: High Octane Fifth Edition” by Drew Knowles
    • “100 Things to do on Route 66 Before You Die” by Jim Hinckley
    • “Route 66: Travelers Guide and Roadside Companion” by Tom Snyder
    • “Moon Route 66 Road Trip” by Candacy Taylor
    • “Here it is! The Route 66 Map Series” by Jim Ross and Jerry McClanahan. (This is one map per state with “a ton” of information about the route and attractions on it.)
  • Software for Route 66 planning
    • Route 66: Ultimate Guide by McCoy Corporation USA
    • Google Maps (of course!)
    • MS Word! (Bet you thought I’d forget that one.)
Books and Maps for Route 66 Planning
Route 66 Books and Maps for Planning

Notes: Again, I don’t have a commission arrangement with any of these products. It’s what I used while planning and while on my trip. The Route 66 Ultimate Guide (software) has been substantially updated since I took the trip in April of 2018.

Pulling it together

Initially, I read through each of the books noted above. Some scanning, but reading many of the chapters. After the initial review, I decided “The EZ66 Guide for Travelers” would by the centerpiece. With that decision made, I worked through each state, checking the information in the other books with the EZ66 Guide. Although the EZ66 Guide is very good, I did find other interesting information not in EZ66 Guide to go into the Word doc.

Next, I created a workplace in my “man cave” and set off on the imagining part of the trip. Set up the laptop to create the Word doc to accompany the trip. Spread out all the materials with EZ66 Guide as the center-point. And, the Ultimate Route 66 Guide app also played a role and would continue to do so during the trip. I’m not going into a lot of detail about my planning because; first, it’s probably boring, and second, the actual trip will be covered in each day’s post. I hope you enjoy the benefit of all this Route 66 planning!

Route 66 Planning by days

While reading all the material, the book “Moon Route 66 Road Trip” identified a 14 day schedule with a few side trips to go from Chicago to Los Angeles. That inspired me to develop this series of blog posts around each day I was on the road. I took 17 days to make the trip and didn’t do any side trips. (I did go through Santa Fe but that’s on the first iteration of the trip.)

Oh, there is one short side trip you’ll see later. Really, I could have taken far longer. An idea you may want to consider is to do the road in several sections, especially if you can’t take so much time away from work. I can easily see making a three to four week trip on Route 66. And break it down into 7 to 10 days at a time. And, hey, I’m nearly ready for the “real” Day 0 – Positioning to Chicago.

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Finally, my Route 66 planning covered the logistics of how I was going to get from “here” to “there” and how to return. To that end, I rented a car with the option to return it in LA and fly back or to drive back. Research uncovered the fact that renting a car near home and driving to Chicago was considerably less money from my budget than flying to Chicago and renting there. Of course, I still had the option to fly back from LA.

The last couple of weeks took up much of my time reviewing Jerry’s book, keying in related notes, and potential stops and sights along the way. I used the EZ66 Guide as a base and created an accompanying Word doc to match the pages, taking info from the other books. My Route 66 planning took a lot of work! If you go, I hope you can make use of my experiences as well as the books I’ve mentioned.

Ready for Route 66, The Mother Road

Summarizing the Route 66 Planning

Summarizing Day 0 – Positioning to Chicago, I kicked off my trip as the last “day” of Day 0. That involved picking up my rental car, packing up everything I thought I’d need for the trip and driving to Chicago. (Fortunately, I picked up the car the day before leaving for Chicago.) Of course, that day involved mostly just driving. My research also indicated that driving to Chicago on Saturday, arriving in the early evening became my best option as far as coping with Chicago traffic was concerned. According to my planning and other “life events”, Easter Sunday was my best start.

Heading out!

And, I woke up to snow on the ground, Road reports of slippery spots. I’m headed out soon in the snow. My Great River Road trip last year started with a snowy day as well. Looks like if I do a July road trip, it might start with a snowy day as well! (Probably not). Pulling all my stuff together, I have the feeling I’m missing something…  Good thing I did all that Route 66 Planning.

On the way. Not doing a lot of touristy stuff, just traveling through Wisconsin. Great scenery but not what I’m here to do. I might see a few things along the way that are worth mentioning. But, off I go: Day 0 – Positioning to Chicago.

Day 0 - Positioning to Chicago
Chicago River in The Loop

And, I made it to my start point! The Chicago River out of the hotel room. Here is a link to the cornerstone post for this trip. And here is a link to the first “real” day on the trip. Of course, that’s the end of Route 66 Planning! So, keep following! It’s all part of the experience from here. Of course, I’ve included posts about the drive back as well.

“Anticipation” by Carly Simon

We can never know about the days to come
But we think about them anyway
And I wonder if I’m really with you now
Or just chasin’ after some finer day

Anticipation, anticipation
Is makin’ me late
Is keepin’ me waitin’

Written by: Carly Simon
(Of course, it’s making us wait while doing Route 66 Planning!)

This Post Has 4 Comments

  1. admin

    Will be on the way on Saturday morning

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