Route 66 Road Trip Guide

The following is what became my Route 66 trip: the places I loved, the places I missed, and some of the detours along the way. I hope each element of this guide is useful to anyone planning a Route 66 trip of their own. 


Below is various elements of the trip I thought might be useful including:

A Day by Day Breakdown

Make it Your Own — An editable and downloadable Google Document

A State by State Breakdown

Trip Cost

Tips & Things to Consider

Please note: I traveled from Santa Monica, CA on September 2nd, 2015 and arrived in Chicago, IL the night of September 12th, 2015 and then spent three days in Chicago for a total of 14 days (with detours). When planning your trip, take into account season/weather changes, gas price fluctuation, and various other changes that might have taken place since I took this trip.

My Route 66 Road Trip Mapped Day by Day

A breakdown of my Route 66 road trip by day denoted by color on the map below — each marker is linked to the post I described that day in, and each color marker represents a different day.

Make it Your Own

Use this link to access the Google document.

To add it to your own document and edit it, simply follow these steps:

1. Open the file through the link above
2. Once in Google Doc, go to "File"
3. Select "Make a copy..."
4. Rename the file as you'd like and save it — it will now be located in your own Google Drive to edit

State by State

Below are all the places by state I either stopped at or had planned to stop and explore with links that direct you to the post it's described in. (Pictures of postcards I bought by artist Bob Waldmire — a definitive artist of the Route 66 trip.)

Trip Cost Breakdown

On the road from Santa Monica to Chicago, IL with some detours, the total cost of the trip was: $1,217.29*

Broken down, that price includes:

Gas: $285.11

Food: $227.88

Stay/Accomodation: $290.22

Experiences: $410.08

Misc: $4

All in all, the trip cost was about $250 more than I initially projected in the trip planner (originally projected to be $982) 

*the final amount does not include the accommodations and gas and some experiences that were divided with the friends I was driving with. It also does not include the cost of souvenirs. 


Tips & Things to Consider

  • Time changes. I didn't account for this at all. So when I had planned to go to a place near the end of the day and the time jumped forward an hour, suddenly the place was closed and there was no chance of making it.
  • Gas prices. They either go up or down in price based on where you start. Fortunately for me going west to east, gas went down #tripbonus
  • Print out everything. Seriously. I thought maybe if, for some awful reason, I lost my phone or it was taken, I at least would have a back-up of my itinerary with addresses, maps, and confirmation numbers. And although my phone is still with me (thankfully), I didn't account for areas that I didn't have any service and couldn't access Google maps.
  • Don't be afraid to adjust the itinerary. I did. It's better to not rush through something you're really enjoying just to make it to your next destination. And on that note...
  • Don't try to fit ten things into one day. I already did that. And that was probably the biggest mistake of the trip. By the end of the trip I was so exhausted. I saw and experienced most of the things I wanted to which was great, but the trip would have been so much more relaxed and probably more enjoyable if I broke down ten hour driving days and didn't try to stop at more than four places a day.
  • Food is mostly going to be diner or take-out. Embrace it. Love it. You'll have post-trip detox. Basically all of my grand plans to save money by going grocery shopping and maybe eating out one meal every other day did not happen. 
  • This trip was a one way. Since I was moving to Nashville, TN it seemed like a good opportunity to also do this road trip, that way I wouldn't need to pay the expenses of driving back. But there's always alternative options like rental cars, hitchhiking (haven't tried that before though), buses and a flight back. 

Related Posts

Browse through all the posts referring to the Route 66 trip.