Route 66 Trip Planning Realities

WHERE IT ALL BEGINS

There is already an enormous amount of documentation regarding the history of Route 66 so I’m not going to bore you with a lengthy dialogue on that specifically.  No, I prefer to bore you with my beginning of Route 66.  I’ve always loved cars and road trips and whenever I’ve been near stretches of Route 66 I’ve been excited to hop on, even for just a short stretch.  Its always been a bucket list item of mine to drive the full length of Route 66, of which I’ve now accomplished half of.  I definitely learned some things in both trip planning before you even leave home and on the road experience that will serve me well when I finish the second half of the highway in a few years.  Hopefully anyone heading out on this adventure themselves will find a useful nugget of wisdom here.

ITS DIFFERENT FROM OTHER ROAD TRIPS

I came into this adventure with numerous successful road trips under my belt where I was able to see a lot of things in a short amount of time.  Many of these trips were more scenic in nature though – like the scenic drives in National Parks or beautiful byways with pullouts for photo ops.  It’s not unusual for my days to be 10-12 hours long and traversing 4-600 miles of backroads on longer days.  
 
With that experience, I split this trip (Chicago to Mid-Point) up into what would normally be 5 relatively average days with 4 overnight stops along the way.  The reality is, Route 66 is not like a scenic highway with pullouts. While there are definitely scenic parts of the route between towns, all of the photo ops are in towns which creates its own set of new to me challenges. Never have I ever had to turn around, go back, circle the block, dodge cars, or come at a photo from a different angle so many times on a trip before.  This adds a lot of time to the trip and seriously slows down forward progress.  

NAVIGATION CHALLENGES

Again, on my other scenic road trips, I was used to having to plan my routes by placing waypoints on Google Maps and saving them in advance of my trip so it would take me on the scenic highways I wanted and stay off the fastest or shortest route like it constantly wants to recalculate you on.  That is borderline unrealistic for Route 66.  I’d probably have 66 saved maps (can only have 10 waypoints per map) to get it to go where I wanted.  

So, knowing this would be different, I ordered 3 books, a set of 8 maps, plus a laminated map.  I thought for sure, armed with all of this that we couldn’t go wrong.  When I found the Begin Route 66 sign (which GPS will take you to) I was excited to begin the journey…we were on our way!  Five minutes later, in a maze of one way congested downtown streets, we were struggling to figure out where our next turn was.  Sure, the paper map may have said “turn on such and such street” but I had no idea if that was in .8 miles or 8 miles.  It was stressful!  Not only that, the navigator has to keep their eyes glued to the tiny print of the maps and hopefully not lose their place while looking around and trying to enjoy the trip.

By the outskirts of Chicago I had pulled into a parking lot and downloaded the blue (free) Route 66 Ultimate Guide app for navigation.  The screen shots in the app store show nice maps and distances to the next turn like any normal Google or Waze type navigation program.  The app itself says “it does not include a live map…this is to increase safer driving, and allows you to experience Route 66 without having to watch an app.”  Umm, okaaaay, but I was desperate so onward we went.  Listen, this thing couldn’t even get me out of the parking lot.  I found my own way to the road and used it for about 15 miles but it was almost like the paper map we already had.  It would just tell you the next turn but no map and I don’t even think it told me distances to the next turn.  There may be other merits like the points of interests but the navigation part was a no-go.

So, into another parking lot I went and downloaded the yellow (paid) Route 66 Navigation app.  While this app wasn’t without its challenges, it did keep me on Route 66 with clear instructions and a visual map.  The books and paper maps rode in the trunk for the remainder of the trip.  I highly recommend bypassing everything else and just hocking up the cost of the app as part of your trip expenses and move on with life.  Now, this does not help with pre-planning…it does best while you are on the route and want to stay on the route.  

We wasted at least an hour, probably more like 2, just sorting out our navigation issues.  It was really a rocky start to a trip and was totally uncharacteristic (and need I say humbling?) for us.  

Another item of note is that neither of these apps are compatible with Android Auto (and I assume Apple CarPlay) so you will be navigating directly from your phone and not your cars in-screen display.  This means you may want to be prepared with a phone mount on your dash (which I wasn’t) to have it visible.  The other thing to think about is which phone to put the paid app on.  If the navigation app is on the same phone that is your primary picture taking phone then you’ll have an added layer of annoyance of always unhooking your phone and disconnecting the navigation to take pics and then hooking it all back up again.  If you are wiser than I was, you’d pay for the app on the phone not taking the pics.

My navigator also wants to remind readers that there is more to being the navigator than reading the map.  For one, they too are along to enjoy the sights and when they look up to see a famous icon then look back to the map, its very easy to lose the place in the route instructions and its very hard to tell if we’ve driven past the next turn or not.  In addition to keeping the car on the route, the navigator also has the added duties of retrieving snacks to keep the driver from getting hangry, topping off water jugs, searching for the pen that fell down the side of the seats, getting the phone ready for an upcoming photo op, finding gas stations and meal stops, etc.  All of these other things take their eyes off reading the map and makes navigating by books and paper maps infinitely more difficult.  So, take it easy on your navigator and pay for the app.

Note – I am not affiliated with the yellow Route 66 app in any way or earn a commission by recommending it.  This is just my true personal experience on the road after using all of these various resources, wasting time unnecessarily, and having a meltdown or two while we got our act together and settling in with what worked best for us.

My last tidbit of navigating wisdom is, yes, the route is mostly well marked.  But, I did experience areas where signs were missing or were confusing.  I would not solely rely on the route markers along the road to be your navigational beacon.

THERE IS MORE THAN 1 ROUTE

Yup, that’s right.  More. Than. One.  So you’ll be driving along and pass a brown Historic Route 66 sign with an arrow to the left and your map or navigation app says to stay straight.  OMG, I’m so confused!  Do I stay straight, do I go back and turn?  There were times when a pole would have 3-4 Route 66 signs, including bicycle routes.  Seriously!  

There is generally what is considered the “old” or “original” route that still exists in some areas and then there are some newer rerouted sections.  Sometimes it has been rerouted several times in a particular town so they put these handy year markers (that mean literally nothing when you are driving) saying choice A is the 1926 to 1932 route and choice B is the 1932 to 1947 route and choice C is the bicycle route or yet another block of years.  Which one is best?  What are you going to miss taking one over another?  

I’ll admit, I have FOMO (Fear Of Missing Out).  Knowing there were sections I wasn’t driving on was making my FOMO kick into high gear, but, a little research helped me make a decision and stick with it.

My pre-planning  research indicated the majority of the sights to see are on the newer sections of Route 66.  And, I discovered while we were on the road that there were little sections of the old road preserved that you could still walk or drive on for some novelty without having to truly drive the oldest route (great for calming the FOMO!).  I’ve also heard the oldest part of the road is the most rough and while the Corvette is a great open road cruiser its strengths do not shine on rough roads riddled with potholes, so for me…the oldest part was a pass. 

Also, the yellow navigation app gives you choices.  Route A is the newer route (and recommended) and Route B is the oldest parts of the road.  It will automatically tell you directions based on which choice you made so just keep with the motto “always trust the GPS” and don’t panic when you see a sign saying Route 66 went left while you went straight…that was likely Route B.  If you want to look ahead, you can look at the attractions in the towns and it would tell you if it was on Route A or Route B which could also help you decide which fits your personal desire of what you want to see or accomplish.

ROAD CONDITIONS

Prior to hitting the road, I had quite a few people mention they were shocked I’d take my Corvette on this road.  They seemed to think the road was left to deteriorate and is in complete disrepair and I’d end up damaging my car by doing this.  I really wanted to drive this all-American road in my all-American car so with some amount of trepidation I set off expecting to be dodging potholes for most of the way.  My personal opinion is just because this is Route 66 doesn’t mean its been left to be overtaken by nature.  Did I experience potholes and rough patches of road?  Absolutely.  Did I experience those same things on nearby roads that were not Route 66?  Also, absolutely.  Don’t get me wrong, I-55 is going to get more attention for roadwork than Route 66 running along beside it but it was in reasonably good shape the majority of the time.  There were areas they were actively upgrading the road surface.  In small towns Route 66 is often their Main street and is upkept as any other Main streets in America are.  In the big cities like Chicago and St. Louis where all of the surface streets are pothole laden disaster zones, Route 66 is no different.  

NUMBER OF DAYS

Who scoffed at the people online saying the full Route 66 takes 3-4 weeks to travel?  <hand raising> That would be me.  It really all comes down to how you want to travel.  I am a “see and go” person.  I do not need to hang around a location for days and experience all the things.  I absorb information and sights quickly, appreciate what is in front of me, snap my pictures to share with all my peeps, then I’m ready to move on to the next sight that awaits me.  Don’t judge me…I don’t judge you for taking cruises every single year.  We each have our own travel style preference and this is mine.  It is definitely not for everyone though.

While I still think 3-4 weeks is excessive, I think 2 weeks is appropriate for the full Route 66 or 1 week is good for doing half at a time.  I did half in 5 days/4 nights and I needed more time (see above, the turning around for photo ops was a huge time suck).  

DAY 1

I started my trip in Gary, Indiana which is only 45 minutes from Chicago.  We had some personal genealogy to do near Chicago before we started so we didn’t actually reach the start sign until about noon.  We made it to our first overnight stop of Bloomington at about 7pm.  This day was okay for us, but if you are interested in stopping and going in gift shops, visitors centers or sit-down Route 66 diners, then you either need to get on the road earlier than noon, or, stop in Pontiac for the night.  (Bloomington was my stop because I was meeting a friend for dinner there)  Pontiac and Bloomington are both large enough to find accommodations of some sort.

DAY 2

We had a few things to take care of in Bloomington and didn’t get on the road until around 10.  Our goal was St. Louis because we were meeting up with another friend and partaking in a Cardinals game that started at 6:45pm.  If we had gotten on the road a little earlier, or we didn’t have a time to be somewhere in the evening, this day would have also been fine.  (Note, I’ve been to Springfield, IL before and did the Lincoln National Monument stuff so I skipped it, but if you stop plan to spend a few hours there).  If you prefer to stop at museums or have a little shorter days and stopped in Pontiac on day 1, then I’d recommend making Springfield, IL your overnight stop.  

DAY 3

Since I had to ditch the Chain of Rocks on day 2, day 3 actually started out backtracking to go back and get it.  It was definitely a must see and glad we did that, but, it added probably 2 hours to our morning.  Our overnight was in Tulsa, OK and this was a long day.  Missouri was probably the prettiest state with rolling hills and pretty trees but if felt like it was never going to end.  It was dark by the time we did the 16 mile stretch of Kansas (which was actually a great little stretch!) and almost midnight when we rolled into Tulsa.  We drove the interstate for the last leg because it was so dark you couldn’t see anything on Route 66 anyways.  I recommend staying in Springfield, MO (if you are coming from Springfield, IL) or in Joplin, MO (if you are coming from St. Louis).

DAY 4

One of my must see stops was the Blue Whale of Catoosa so keeping with my theme of backtracking, we left Tulsa and backtracked to Catoosa to see the whale.  Then we went back thru Tulsa and on to Amarillo, TX.  Although this day wasn’t as long as day 3, it was still long.  If you stayed in Springfield, MO then I’d recommend Tulsa then doing the next leg to Shamrock, TX.  If you stayed in Joplin, MO then I’d recommend Oklahoma City with the next leg to Amarillo, TX.  

DAY 5

We started out by doing the Amarillo stretch of Route 66 since it was too dark the night before, and it was a great stretch but it required a lot of turning around and going back.  It was a busy little downtown stretch.  You could also get out of your car and walk, but this was Texas in June so we opted to turn around numerous times.  We made our way over to the Mid-Point in Adrian which marked the end of our trip.  We went back to Amarillo and had lunch at the Big Texan before we started our journey back home.

ACCOMMODATIONS

I really wanted this to be a great Route 66 experience where we saw all the things, ate at diners, stayed at old motels with neon lights, etc.  I once stayed at the Historic Route 66 Motel in Tucumcari, NM (right up the road from the well-known Blue Swallow motel) and in my mind I was expecting motels like these all along Route 66.  News flash – these kinds of motels are few are far between on the eastern half of the mother road.  There were some more as you got into Oklahoma and Texas but Illinois and Missouri in particular seemed to not have many choices.  There was one I was really interested in but the recent reviews scared me off.  So that leaves traditional hotels or things like Airbnb or VRBO.  I ended up using Airbnb because I could get a house close to Route 66 for essentially the same price as a hotel and gain privacy, separate bedrooms, better parking, etc.  I expect when I do the western half of the trip that I’ll be able to have more of the motel experience (Wig Wam’s or bust!)

FINAL THOUGHTS

Pick a handful of things you really want to see as the core of your trip.  My must sees were:

  • The “Begin Route 66” sign
  • As many of the “Giants” as possible
  • Blue Whale of Catoosa
  • Shamrock Conoco
  • Pontiac murals
  • Leaning Tower of Texas
  • A specific mural in Yukon, OK
  • Round Barn of Arcadia
  • Pops store of Arcadia
  • Corvette mural in Joplin
  • Cuba murals
  • Chain of Rocks bridge

As long as you see the things your really want to see, then everything else is a bonus.  Take the time that your schedule allows and do the best you can with what you have to work with.  I chose to spare some funds on extra hotel nights and food and shorten the trip and while it had challenges it still worked out and I saw everything on my list, along with many, many more things!  

They are actively revitalizing what they can on Route 66 and they rely on visitors like us to spend our money there to help them continue to make progress.  Route 66 will turn 100 years old in 2026 so there is no time like the present to get on the mother road and enjoy it from pier to pier (the Navy pier in Chicago to the Santa Monica pier in California)!