Route 66 in Oklahoma – All the highlights!

Welcome back to our photo series depicting our epic Route 66 adventure. If you missed them, you’ll find the photos from the previous states here.

In this post we’re heading through Oklahoma, home to everything from drive-in movie theatres to giant whales! Let’s get started.


A road trip involves a car, and since you have a car, why not take advantage of a classic drive-in movie experience. We had ours in Oklahoma, at the Winchester drive-in, the oldest drive-in movie theatre in Oklahoma, and one of seven surviving in the state. Drive-in’s are a wonderfully nostalgic way to enjoy a movie, plus you usually get to see two movies at a great price. Recommended!

Naturally Oklahoma has plenty of Route 66 themed murals.

And Route 66 themed nostalgia

And a giant round barn. Built in 1898, and the only round wooden barn surviving in Oklahoma. Find it in Arcadia.

There’s no shortage of classic motels either with that beautiful neon signage.

Not all the parts of Route 66 survived. This old road bridge was replaced by a more modern version capable of carrying today’s traffic volumes.

I have to admit to not knowing much about sports – any kind of sports. This guy was obviously a pretty decent baseball player though, given that his hometown built a statue to him. Find out why, here.

One of the big attractions of Route 66 in Missouri are the Meramec Caverns – a large underground cave system. For Route 66 buffs though, the real attraction are the barns advertising the caverns. Once there were hundreds of these barns all across roads in America, including Route 66. Not many survive, but you can still find a few if you keep a lookout!

Oklahoma also has it’s fair share of classic Route 66 properties. This is the “Milk Bottle Grocery”, a 1930 building which operated as a grocery store for decades, and nowadays seems to vary with what it’s operating as. One thing that doesn’t seem to change is the giant milk bottle up top serving as advertising for an Oklahoma staple – Braum’s Ice Cream.

Another giant bottle, but this one is a modern Route 66 attraction. “Pops” restaurant opened in 2007, with walls decorated in soda bottles – all of which are available for purchase. No Route 66 attraction is complete without a giant “something”, in this case a 66ft tall four ton model of a soda bottle, complete with drinking straw. Definitely worth stopping for, and nice to see a modern business investing in the Route 66 dream.

Moving on, and of course Oklahoma has it’s fair share of old style gas pumps…

Giant flour mills…

Enormous concrete totem poles…

Signs to highlights along Route 66…

And towns that time forgot.

Many businesses still survive along the route.

Whilst many others do not.

Tulsa has this lovely tribute to Route 66 – a large statue of a car and it’s occupants tackling the route. Some of whom seem less impressed than others!

Just outside of Catoosa is the famous Blue Whale attraction. If it’s a hot day, a dip in the waters is recommended.

There are of course classic road bridges to peer at.

Some of which take traffic, other which do not.

The Route 66 marker appears on the route from time to time, to help you find your way.

And like every other state on Route 66, Oklahoma also has it’s own Route 66 museum!

Which of course, features a barbed wire collection.

And a giant sign! A handy way to end today’s photo essay. Now for a few tips to help you out if you’re planning your own Route 66 Adventure

Tips for Planning your own Route 66 Adventure

If you’re planning your own Route 66 adventure, we’ve got a bit of reading for you!

• First, be inspired by photos from all the states we visited, by checking our photos highlights from each Route 66 state: California, Arizona, New Mexico,  Texas, Oklahoma, Kansas, Missouri & Illinois
• Next, check out Jess’s comprehensive guide to planning a Route 66 trip
• Then, take a look out our incredibly detailed day by day 2 week Route 66 itinerary, which covers all the sights you want to see, route tips, lodging options and places to eat. We also have a 1 week Route 66 itinerary
• If you’re new to driving in the US, check out my tips for driving in the US to get you started
• Not sure how much it’s all going to cost? We’ve got you covered with our guide to travel costs in the USA
• Finally, take a look at this book – the best way in our opinion to successfully navigate the entire length of Route 66 as faithfully as you can. We followed it the whole way, and even met the author, and couldn’t have done without it!

Enjoy your Route 66 trip, and let us know which has been your favourite state so far in the comments below!