Known as the Mother Road, Route 66 must have been one of my favorite trips ever. It runs from Chicago to L.A. for almost 3900km, and for us, it represented the Ultimate Road Trip, being the most famous road in the world. It passes through 8 states: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California.

So, for a road trip lover like me, driving Route 66 was definitely on my bucket list! If you go off-season (like we did) its pretty much like driving through frozen in time ghost-towns as there are absolutely 0 tourists. In fact, most people were even surprised of seeing us. Might be a bit cold though! But it will get warmer and warmer as you drive West.

Here are my 15 MUST DO during your road trip along ROUTE 66!

1. VISIT ROUTE 66 STARTING POINT IN CHICAGO

Every proper Route 66 road trip should start in Chicago, the Windy City. There are many places to visit here (do not miss the famous Cloud Gate!) but make sure to start your way West at the Route 66 starting point. The original sign is nestled between skyscrapers, in E Adams Street.

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2. VISIT JOLIET PRISON – BLUES BROTHERS

I have been a fan of The Blues Brothers for as long as I can remember. As a kid, I must’ve watched their films a thousand times! And I also love abandoned places, so I was pretty hyped when we got to Joliet.
The prison has been closed and abandoned for more than 15 years now. I wanted to get inside so bad but it was absolutely imposible. There is police in the parking lot watching out for people trying to jump inside and its fenced.
Just in front is what used to be women’s prison. We went through the back, as there was a gap in the fence and got inside the backyard. Our adventure didn’t last long though, as a police man somehow spotted us and asked us to step away 2 minutes later 🙁

3. SLEEP IN AN ORIGINAL ROUTE 66 MOTEL

All over Route 66 there are hundreds of iconic and cool motels, with their neon signs and theme rooms. We even stayed at one that had teepee rooms! To make it even better, most of them are quite cheap (between 50-100$ a night for a double room), and owners are super kind locals that will enjoy a good chat and will tell you about the history of the motel. If you are like us, and don’t really plan ahead, don’t worry as you can just pop by and they will most likely have available rooms.

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4. STOP BY FOR PICTURES IN AN OLD GAS STATION

Nothing captures the essence of Route 66 like these gas station. They don’t serve gasoline anymore, however they are like a museum, full of cool vintage rusty stuff and stories. We made sure to stop in every single one of them!

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5. WATCH A MOVIE IN A HISTORIC DRIVE-IN THEATERS

There are still a few operating drive-in cinemas along Route 66, even though most of them are between Illinois and Oklahoma. They are seasonal though, which means they are closed during the winter. Tickets are very cheap, so make sure to plan a sleepover in a city close by.

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6. DRIVE THE “REAL” ROUTE 66

The original highway was decommissioned, which means Highway 66 no longer exists and does not appear in maps. This causes most people to just drive on the new interstate that more or less follow the same path. In fact, in some places, the original route is impassable. However, you can still drive through a big part of the original Route 66, and I couldn’t recommend it enough. Now, the most useful thing I found when preparing our trip, here is a link to a google maps map that will help you follow the REAL road. You are welcome 🙂

https://bit.ly/2YE9Av0

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You may notice we had 3 different cars throughout our trip… but that will be a story for another post!

7. SLEEP IN A HAUNTED HOTEL

The Monte Vista Hotel in Flagstaff, Arizona has hosted famous guests as John Wayne or Gary Cooper. The hotel was the place of death of a robber, and two prostitutes, and there have been countless reports of strange phenomena. Some people have reported seeing a little boy wandering the halls, a woman in a rocking chair, hearing a baby crying in the basement, and many other stories. We didn’t get lucky though! But loved the hotel and the decoration.

8. VISIT CADILLAC RANCH

Route 66 crosses briefly through Texas, and the iconic Cadillac Ranch in Amarillo is a must! Be aware it gets really really crowded here so, if you can, go early in the morning. Graffiti is allowed!

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9. GET A ROUTE 66 PASSPORT

The Route 66 passport is only available through Arizona, and there is no better guide to the area! Make sure to pick up yours at any visitor centre or participating business, and then you will have to fill it with all the required stamps (there are 10). Inside the passport you will find directions and information on each town and how to collect all the stamps, and how to redeem it after you have finished. Sadly, we didn’t get them all, as some visitors centres were closed when we passed by, and we didn’t know that you can also take a picture of it and show it at the next centre.

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10. VISIT A METEORITE CRATER

During your Arizona stretch of Route 66, another must-see its the Meteor Crater east of Flagstaff. It was formed by a meteorite 50.000 years ago, and it was used by Apollo astronauts as practice because of its resemblance to the moon surface. Unfortunately you can’t walk down into the crater, but the visitor centre has a view point and lots of info. Its honestly a breathtaking place, I was surprised of how big the crater actually is. Worth the visit!

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11. TAKE A DETOUR

Now, taking a detour means getting off of Route 66 to explore near-by places, so many people decide to just stick to Route 66 original path, but I do encourage taking a detour. There are lots of options, but we decided to visit Horseshoe Bend, Antelope Canyon, Monument Valley, Grand Canyon and Vegas. So our detour actually took 4 nights (our initial plan was only 1 night 😂), and right after we drove back to where we had left and continued our Route 66 so we wouldn’t miss anything.

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12. EAT AT THE BIG TEXAN STEAK RANCH

Located in Amarillo, Texas, the Big Texan Steak Ranch is home to the world famous 72oz steak challenge. If you manage to eat it all, you will eat for free! This restaurant was featured in Man vs. Food, and it also has a cool motel nearby. Even though we didn’t go for the steak challenge, food was fantastic, and the place itself is really cool.

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13. VISIT BOTTLE TREE RANCH

This is such a complete random place that the owner, Elmer, decided to create following his passion for collecting glass bottles. It is literally a forest of bottle trees in the middle of the California desert. There are also all kind of vintage objects, and even an old Jeep. We arrived as sun set, and we were overwhelmed by how many things there are and how truly different this place is.

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14. LISTEN TO “GET YOUR KICKS ON” WHILE DRIVING ROUTE 66

The essence of Route 66 is driving. There will be endless hours on the road, passing through ghost towns and driving middle America country side. There is no better way of passing time than listening to music. So, another must do, is listening to Route 66 songs! Even though Get Your Kicks On Route 66 is a classic, there are many other songs about the Mother Road. So, get on Spotify, find a cool playlist (or create your own), play it non-stop and enjoy the road!

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15. END YOUR TRIP AT THE SIGN IN SANTA MONICA PIER

The Route 66 doesn’t end until you get to Santa Monica Pier, where there is a sign that marks the end of the legendary American highway. You have to visit it to properly conclude your trip, and obviously take a picture! There will be hundreds of people doing the same, but probably none of them will have driven the whole Route 66!

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Hope you found my 15 must-do list of Route 66 useful! If you have any questions feel free to ask in the comments below.

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