Driving Route 66 – Places To Visit During A Route 66 Road Trip

Everyone living in North America has heard of driving Route 66, the infamous Route 66 highway which connects Chicago to Los Angeles. It’s a stretch running 2,448 miles.

The development started in 1920 with the growing number of people purchasing automobiles. At this time, the federal highway official decided to grow the route and give almost every highway within the US a numbered system.

Driving Route 66 Road Trip

Driving Route 66 explore Rt 66 roadside attractions

“Route 66” became a very popular road, because of the US States that it passed through. This route is also a very popular truck route because much of the road is flat with make it easier for truckers to keep a stable speed going through the US.

The Dust Bowl of the 1930’s gave many farming families an easy route to California when they went searching for work and during the depression when money was hard to earn. The store owners along the highway would benefit from the traffic flowing through. It helped grow the gas stations and mom-pops businesses located along the route.

route 66 road trip stop: the old gas station

Route 66 passes through the following states in order: Illinois, Missouri, Oklahoma & Kansas, Texas, New Mexico, Arizona then right into California. It is important to know that all of these States offer travelers a new and exciting experience with historic spots, city centers, people and overall beauty.

For those of you who have NOT experience driving Route 66 today, but are planning on taking the trip then there are many things to do on route 66 road trip because of the structure of the highway.

Let’s visit a few popular spots along the highway starting in Chicago, IL

route 66 start chicago

In Chicago there is a lot of history because it used to be the “New York” of the United States before the development started in Manhattan.

If you’re looking for a place to eat during your travel then stop by Lou Mitchell's Restaurant

or take a break at Dell Rhea´s.

If you’re looking for more excitement then just eating at a few restaurants then visit the DeCamp Junction because in the 1930’s Al Capone and his crew use to gather there and was considered one of their hideouts.

The National Route 66 Organization has invested a lot of money into restoring many historic buildings along the route and a good example of this is the Rivera Diner from the 1950’s.

If you’re looking for a museum then visit the Hall of Fame in Pontiac.

Don’t forget to visit Sears Tower located downtown Chicago and enjoy a drink and the beautiful city lights at “The Signature Room” at the 95th Hancock Center. Explore more Illinois main attractions along Rt 66 here.

Chicago Skyline old route 66 road trip

While on your route 66 road trip, you’ll enter the State of Missouri and the culture changes.

You’ll notice a shift in weather especially if traveling during the colder seasons. Missouri has several things that you can do starting with the Old Courthouse which is part of the

It was built during 1862 during the Civil War and is now half a museum which features galleries and historic items. There is NO fee for entering the courthouse and the museum. Next, there is a Route 66 State park which was recently built and has had many reviews for being an awesome place to stop by.

Along the route there are many old taverns that have been around since the beginning and have been renovated. When driving Route 66 make sure to stop by, because ‘you’ will be a part of the 1940’s history. Or have a quick look at the world’s largest rocking chair at “Fanning 66 Outpost” just 4 miles west of cuba, Missouri.

If you’re looking for a place to stay then you can stay at a historic Route 66 motel, the Munger Moss Motel.

route 66 Milk Bottle Building Oklahoma City
Braum’s Milk Bottle building in Oklahoma City on Route 66

The next stop along the route will be the State of Oklahoma

Oklahoma is home to Garth Brooks the legendary country singer and many have said that this route has some of the best places ever. There are parts of the old brick road which was the first initial ground work for “Route 66”

There is the Blue Whale of Catoosa, Catoosa, OK 74015.

You can also visit the Route 66 Museum Address: 2229 W Gary Blvd, Clinton, OK 73601.

There is the Metro Diner which has some excellent food and bit of history because Elvis ate there which you’ll notice because of photos on the wall. Pay a visit to the world’s largest (66 ft.) soda bottle known as the POPS which was built from soda bottles like the windows, diner and has a gift shop too.

Route 66 road trip stops - Pops sculpture in Arcadia on Route 66
Credit: thanks to Randy Lane, CC BY-NC 2.0

Photo 6: Pops sculpture in Arcadia on Route 66 road trip

Want to stay overnight in Oklahoma, the historic Campbell Hotel in Tulsa, is located right on Route 66 in midtown Tulsa.

This pretty much covers the first half of the trip, however we have a lot more attractions to cover during the second part.

We’ve discussed driving Route 66 from Chicago, Missouri and Oklahoma and now it’s time to cover the States that will bring you into California – Go to Route 66 Attractions.