Did you know that Route 66 turns 100 this year??
The famous route is officially 100 and we are FINALLY travelling part of this iconic road trip!
Route 66 is the famous USA route that stretches 3,800 kilometres across the country from east to west. The starting point in Chicago, Illinois and the finishing point in Santa Monica, California.
Now this guide in particular features our journey from St. Louis, Missouri to Oklahoma City, Oklahoma. I would absolutely love to finish the rest of Route 66 someday but the beauty of this road trip is that you can start and stop anywhere you like.
We spent a week exploring the heartlands of America and seeing all of the beauty it has along the way.
This is 100% a bucket list road trip that I’m so excited we got to explore even for a part of!
Save this guide for your future Route 66 trip!📍
My ultimate day-by-day Route 66 guide ⬇️
Day One – St. Louis, Missouri
Fly into St. Louis or drive if you’re coming from the Route 66 start in Chicago!
Someday I’d like to fully complete Route 66 by going from the very start in Chicago. But I do think we picked up Route 66 at the perfect point as there really was so much to see and do along our journey.
It was super easy to fly into St. Louis and we picked up the perfect rental car. I wanted something that screamed “road trip!” and the Jeep Wrangler was a really fun pick.
Also excellent because I have a million suitcases that I travel with and it fit everything.
🏙️ Stop at the Gateway Arch National Park
Did you know that the Gateway Arch is said to be the “gateway to the west”? It’s the perfect start to our Route 66 adventure!
The Gateway Arch National Park is also free to explore. They have a really neat museum underground beneath the arch that I would really recommend popping into.
You can also go UP the arch itself! Now that requires tickets, I’d recommend buying in advance to ensure availability.
I think next time I could brave the journey up! But otherwise, take in the sights, the Gateway Arch is actually double the size of the Statue of Liberty, which is wild!
I’d recommend visiting either around sunset for beautiful golden hour shots or right when the museum opens for the day.
🍻 Cheers! Go on a brewery tour at Anheuser-Busch Brewery
Did you know that the home of Budweiser is in St. Louis?
I had no idea until our visit! As an avid beer connoisseur (aka, Joe just likes beer), we had to plan a visit!
What I liked about the Anheuser-Busch Brewery is that they have a bunch of different tours for different interests. We did the Day Tour which is kind of a small mix of everything. But there are more in depth ones available and even more low-key ones too.
🍝 Toasted Ravioli at Athonino’s Taverna on The Hill
I’d HIGHLY recommend a visit to The Hill when in St. Louis. It’s the Italian district of the city and wowwwww truly the best restaurants are here!
We stopped into Athonino’s Taverna as we heard that they had some of the best toasted ravioli and holy smokes, it was AMAZING.
Our waitress Jessica gave us the best recommendations so we also tried the meatball pasta and obviously couldn’t turn down mozzarella sticks. 10/10 a must visit!
Antiques Shopping on the The Hill
After getting your fill of food in the Hill, if you’re into antiques, you need to go to The Hill Antique Market.
You can find anything and everything there! It’s kind of like an antiques wonderland.
Hotel for the night? Stay overnight at The Royal Sonesta Chase Park Plaza St. Louis
This is a pretty neat hotel, centrally located! Though I do think St. Louis is probably a city more for driving than walking around.
There is a movie theatre attached so the lobby smells amazingly of fresh popcorn. And they have a pool here too! We ate lunch by the pool on our first day and the food options were pretty great.
Day Two – St. Louis to the Ozarks
And today we’re officially beginning our Route 66 drive!
Now that we’ve enjoyed some time in St. Louis, we’re hitting the road to begin the adventure!
🍦Ted Drewe’s Custard Ice Cream on Route 66, yum!
Ok you’re first Route 66 stop is Ted Drewe’s ice cream! Because I feel like starting a journey with ice cream is a reeeeeally strong move.
They’ve been a famous staple along Route 66 and serve up ice cream “concretes” which is essentially what I can describe as a McFlurry but with about a million different toppings and mixes to choose from.
Of course, they have pretty much any ice cream treat you could ever want on the menu too, so go wild!
(also, so good we did this TWICE!)
🪨 Meramec Caverns are such a hidden gem along the route
This is a really cool stop off of Route 66 and one that I think everybody should do on their drive.
I had no idea that caves like these existed in America!
You can book tours of the Meramec Caverns and the tour lasts roughly an hour. You’ll wander through the depths of the caves and honestly it is one of the neatest nature things we’ve ever done!
Make sure to bring a jumper or jacket as it can get a bit chilly down there!
⛳️ Check into Old Kinderhook Resort and Golf Club for the night
Stay overnight in the Ozarks!
We were booked into Old Kinderhook Resort and Golf Club for the night.
Definitely a beautiful spot for golf fans and it was a super relaxed atmosphere here. It was a bit hot during our stay so no one was able to sit outside, but I imagine a cool, crisp evening here by the fire pits would be PERFECT!
Here are some options of spots you can book from booking.com for holiday homes.
Day Three – Ozarks to Tulsa, Oklahoma
Are you ready for your big driving day along this stretch of Route 66? This drive will take us from the Ozarks, through Kansas and finally into Oklahoma!
This is a really fun drive as there are so many fun, quirky stops along the way. And it’s just a beautiful stretch of the open road!
⛽️ Gary’s Gay Parita Station
This is a super quirky stop along Route 66! Gary’s Gay Parita has been a Route 66 staple for years. It was originally owned by Fred and Gay Mason, who loved welcoming visitors.
It’s perfect for photo ops and a fun wander around! They even have free sodas at the back, a tradition that stands from when Fred and Gay would offer refreshments to those passing through.
Pick up some fun souvenirs, Joe bought a fun Route 66 shirt!
🏘️ Red Oak II, it’s a recreated historic village celebrating small-town Americana
This is a pretty neat stop! Created by artist Lowell Davis, who grew up in Red Oak, in adulthood he returned to his hometown to find it was more of a ghost town.
So he ended up buying the houses and moving them to his family’s plot of land, where he created Red Oak II.
It’s a huge, spacious village like spot. Truly, a recreated historical village preserved in time.
It’s free to walk around and have a wander, take photos and enjoy!
🍿 Stock up on snacks at Nelson’s Old Riverton Store in Kansas
In your Kansas stretch of Route 66, you can stop at Nelson’s Old Riverton Store.
Did you know that there are only 13.2 miles of Route 66 in Kansas? It’s a blink and you miss it kind of stretch of road!
But I would absolutely stop off at this general store for some pick me up snacks and treats. They have ice cream at the back AND pie!
💯 Route 66 Musical Highway
I’m going to be honest, we drove up and down trying to get this right before eventually figuring it out.
Coming into the city of Tulsa, you can drive along the Route 66 musical highway and you need your right tire to hit the pavement in perfectly exact way and you’ll hear “This Land Is Your Land” from the music of your very own tires!
🍸 Valkyrie for cocktails
Woohoo, you’re in Tulsa for the night and this is one of the best cities! We loved it so much!
Make sure to head to Valkyrie for the best cocktails.
🔥 Dinner at Amelia’s, pro-tip, book the barstools by the kitchen!
About a two minute walk away from Valkyrie is Amelia’s. The food here is absolutely DELICIOUS.
It’s a must-book in my eyes!
I’d recommend sitting at the barstools / counter by the kitchen. It’s a really fun atmosphere to be right in the midst of it all. And despite being right next to the open kitchen, the atmosphere is perfectly cosy and romantic.
🎶 Live Music show at The Colony, live music but feels like you’re in a living room
After dinner, hit up The Colony for live music. This made for a REALLY fun end to our night.
It’s a really relaxed atmosphere and kind of feels like you’re watching a show from your coolest friends house.
🏨 Overnight at The Mayo Hotel
We really enjoyed our stay in Tulsa and The Mayo Hotel was the perfect spot to base ourselves!
Day Four – Tulsa to Oklahoma City
It’s a big day out in Tulsa before you’ll hit the road for a sunset drive along Route 66 to Oklahoma City.
Enjoy every minute, Tulsa is so fun!
🥞 Classic Route 66 diner breakfast at Tally’s Good Food Cafe
You can’t drive Route 66 without stopping for classic diner food!
Tally’s Cafe was the perfect place for this. It’s got those amazing classic, cool diner vibes.
And the best good old fashioned American breakfasts! Fried eggs, toast smothered in butter, bacon, fluffy pancakes!
My favourite thing? The endless coffee refills of course.
🤠 You can’t miss Buck Atom’s Cosmic Curios! Giant statues and Route 66 photo ops!
This is probably one of your most iconic Route 66 stops, Buck Atoms!
Giant statues and an old petrol station turned roadside sensation. Get your pics with Buck Atoms, the Space Cowboy and Stella Atoms, the Space Cowgirl!
DECOPOLIS Discovitorium
Right next door to Buck Atoms is DECOPOLIS Discovitorium, which is a really fun and magical gift shop.
I’d REALLY recommend popping in. It’s super visual!
🎬 The Outsiders House Museum
For fans of the book and fans of the film this one is for you.
This is the house where The Outsiders was filmed in 1983. They’re recreated and staged the home so it looks as it did in the film and features really neat memorabilia from the film and cast members.
🎶 Bob Dylan Center
If you had no idea that there was a Bob Dylan Centre in Tulsa, that makes two of us!
But we discovered it and had to go! It’s a really cool one for Dylan fans to check out, it has his largest catalog of memorabilia in one spot.
🥩 The ultimate date night at Bull in the Alley, a speakeasy steakhouse in the city
WOW. You absolutely have to have dinner here!
One of the best meals of the trip and truly, they were all so good!
The Bull in the Alley is a speakeasy style steak restaurant in Tulsa. The food is incredible! I would also very much recommend getting a martini from their martini bar cart! They bring it to your table and make it right in front of you.
So much fun!
🌅 Sunset drive along Route 66, spotting all of the neat neon signs to Oklahoma City
After dinner, we had leisurely drive to Oklahoma City. I really wanted to capture photos and videos of all of the neon signs on the way!
We kind of miscalculated though as summertime means sunset is quite late.
So a lot of neon signs weren’t quite lit yet in Tulsa – depending on the time of year, check out timings or maybe go for a sunset drive around the city the evening before!
🛏️ Spend the night at The National
We’ve made it to Oklahoma City for our final stretch of Route 66!
Definitely book into at The National, this was such a beautiful hotel!
Day Five – Oklahoma City
Much like Tulsa, Oklahoma City is a really fun city to explore!
🤠 A visit to the National Cowboy & Western Heritage Museum
Start your day with a visit to the National Cowboy & Western Heritage Museum.
This was a pretty interesting museum visit which explores both the roles of cowboys and cowgirls in the west and Native American heritage.
They also have a Route 66 section in celebration of the 100 year anniversary too!
🗺️ Exploring OKC’s Bricktown Canal + Uptown 23rd District
There are so many great districts to explore in Oklahoma City.
I’d recommend hanging out around Bricktown Canal – you can even get a water taxi up and down the canal.
And the Uptown 23rd District is the old Route 66, which makes for some pretty neat signage! They were doing some major construction to the area while we visited but you can still absolutely get the vibe of everything while there.
🌮 Tacos and margs at Oso in Paseo
Ok, Paseo has to be on your list to explore, it is SUCH a cute area!
And I’d 10/10 recommend Oso for tacos and margaritas. Everyone was super nice in here plus you can get happy hour tacos depending on the time you visit!
🥤 End your trip at POPS Soda Ranch, it’s a classic!
WOW. This is a seriously incredible Route 66 stop!
POPs is a really cool soda ranch right on historic Route 66 in Arcadia, Oklahoma.
It’s a diner that you NEED to get yummy food and root beer floats in! They also have over 700 soda flavours on site?! We picked up bottles of ‘Route 66’ Beer. How fun!
Plus they actually are a working petrol station?!
And well, there’s no way you could possible miss the iconic 66-foot pop bottle lights up every night! My advice is to get here around golden hour for that perfect glow that leads into the sunset!
Would you travel along Route 66?!
I so hope you enjoyed going on this journey with us exploring part of Route 66!
We loved travelling from St. Louis to Oklahoma City!
Make sure to bookmark this post for your future Route 66 planning!
We had an amazing adventure, saw the coolest sights, met the best people and I can’t wait to come back to do the rest of the route someday!
Kelly xoxo