My Route 66 Travelogue: All the Details about My Road Trips

I’m in the process of driving all 2500 miles of Route 66 from Chicago to Los Angeles. But I’m doing it in pieces, pretty much state by state. I’ll keep this post updated with my latest trips as well as links to other posts I’ve written to help you plan your own Route 66 trip. 

I was born and raised in Tulsa, OK with the Mother Road practically in my backyard, but it wasn’t until a certain Pixar movie came out that I took a little more interest. Tulsa has done a lot to preserve and play up our spot on the route in the last decade or so, but I’d never even considered Route 66 outside of our area. 

But I’ve always been drawn to kitschy roadside attractions and classic Americana so when COVID had me locked down from traveling too far, I decided a couple of day trips to see all of Route 66 in Oklahoma would be a fun diversion. 

Well I’m a project person at heart and I love a far fetched but achievable goal so after I started doing the research, I decided to drive the entire route. But my travel tolerance isn’t very high when it comes to days on the road (surprising given my profession, I know) and I knew I’d want to cover it really thoroughly for my blog so I decided I’d break it up into numerous trips and start knocking them out as it fit into my schedule. 

Because I live in Tulsa, I hop around and do day trips here and there, shorter overnight or two night trips in either direction, and often double back to visit  places I didn’t get to stop last time. As I start doing trips into states farther and farther from home, I’m sure they’ll get a little longer.…

Besides personal intrigue, my big mission for traveling the entirety of Route 66 is to help other people who want to take this trip. So most of my content on my blog is geared towards travelers who are driving the entire road continuously or are at least doing a large chunk of the road on one trip. 

So even though the way I’ve approached this project probably won’t be helpful to anyone (unless maybe you live in Tulsa and you’re interested in knocking out the Route over a year ; ) I figured I’d write up my trip segments and itineraries just in case you’re as nosey as I am and just like to read about what other people are doing. 

I’ll catalog this in reverse chronological order so the most recent trip I’ve taken will be described first and the farther back you go towards the beginning. 

But first, here’s a rundown of all of the Route 66 posts I’ve written so far:

Route 66 Missouri Attractions: Everything You Need to Know about the Mother Road in Missouri

Route 66 in St Louis: What to See & Do in the Largest City Mid-Route

Meramec Caverns: The Best Route 66 Roadside Attraction in Missouri

Route 66 through Kansas: Only 11 Miles But So Much to See

Livin’ on Tulsa Time: The Best Route 66 Stops in Tulsa

The Best Route 66 Attractions in Oklahoma

St Louis, MO to Springfield, MO

March 2022

I did this portion of the route by spending two nights in St Louis. I drove from Tulsa to Rolla, MO on I-44 and then got off the interstate and drove from Rolla to St Louis on Route 66. On day one, we had lunch in Rolla at the Tater Patch (a friendly roadhouse style restaurant) and started picking our way east towards St Louis.

We stopped at Totem Pole Antiques in Rolla and pulled over to take pictures of the big hillbilly at the now abandoned Mule Trading Post just outside of town. St James and Rosati looked like neat towns and a place I’d like to go back to poke around a bit more. We stopped at the Fanning Outpost General Store for a bathroom and a drink and it’s a very cute place. Then back on the road to Cuba where I checked out the Wagon Wheel Motel and decided that I would 100% be back. The drive past Cuba towards the outskirts of St Louis was really pretty and we stumbled upon the Shamrock Court which they’re in the process of completely renovating. 

The route forks at Gray Summit into PRE and POST 1932 alignments and since we were ahead on time for the day, I decided it wouldn’t be a big deal to basically drive a big loop to knock both routes out so I could tell you which was the best one to take. In hindsight I should’ve just done one route on the way up and one on the way back, but I was worried I’d be more pressed for time coming home. Well it ended up being a lot more driving than I thought, but we did it. We took the Pre 1932 route first which basically follows Highway 100 and it’s the much longer and more scenic route. We passed beautiful scenery and the Big Chief Roadhouse before hitting a bunch of traffic in the St Louis suburbs. I think all of the traffic was what made it take so long, but I always think it’s interesting driving through towns and seeing how people live. It got more upscale the closer we got to town and then we turned right onto Kirkwood Road (Highway 61) and drove up towards I-44 to head back to Gray Summit and do the post 1932 route. 

Kirkwood (not really sure if it’s considered a neighborhood, suburb, or town) is a beautiful area and a place I’d definitely go back to spend more time in St Louis. It didn’t take very long on I-44 to get back to Gray Summit and back onto the route. The post 1932 alignment didn’t take nearly as long and quite a bit of it was actually on I-44. There honestly wasn’t much to see on this part of the route. 

Once we hit Kirkwood on the outskirts of St Louis, we jumped back on I-44 and headed downtown to check into our hotel since it was early evening and we were ready to get settled in and have dinner. We stayed at the Magnolia Hotel downtown and had dinner at Sugarfire Smokehouse downtown. 

We spent the whole next day trying to follow Route 66 spaghetti through the city (seems like there are 27 different routes through St Louis) and doing a few different attractions. We started on Tucker Boulevard downtown and followed it to Gravois Ave and then onto Chippewa St and then to Watson and then turned onto Kirkwood Rd (that’s all Route 66) to have breakfast at Spencer’s Grill. It was just okay, but a very cute, old fashioned spot. From there we kept going north on Kirkwood Rd to Manchester Rd (turn right) to McCausland Ave (turn left) which will take you up to Forest Park (one of the oldest neighborhoods in St Louis and home of the 1904 World’s Fair). 

We spent a bit at the Missouri History Museum (the St Louis Art Museum and St Louis Zoo are also in Forest Park and they’re all free) before making our way back towards downtown and across I-270 to see the Old Chain of Rocks Bridge. You access it from the Illinois side and it’s got to be one of the best places to actually walk across the Mississippi River (only bicycles and pedestrians are allowed). When we finished at the bridge, we crossed back into Missouri and had a late lunch at the Crown Candy Kitchen, which is probably my favorite Missouri Route 66 dining experience so far. 

We doubled back to Ted Drewes which we had passed early for some concretes (DO NOT MISS THIS IN ST LOUIS), and then parked the car back at the hotel and walked to the Gateway Arch. Tickets were sold out to go to the top that day (spring break), but we spent quite a bit of time down in the museum looking around. 

We got up pretty early the next morning, checked out, and headed back west on I-44. Every road tripper appreciates a good gas/restroom/snack stop so you need to know about Wally’s. It’s not quite as good as Bucee’s, but same general idea. It’s off I-44 west of St Louis and very much worth a stop if you’re on the interstate. 

I attempted to pull over at Route 66 State Park, but it was more complicated than I thought (I think you can only access it from an exit going east bound?), so I’ll have to check it out another time. 

We got off the interstate in Stanton to tour Meramec Caverns, and it’s very much worth the hour and twenty minute tour. You don’t need reservations, you can just show up. Then we booked it down the interstate back to Rolla where we had lunch at A Slice of Pie. It was VERY good and a great pick if you want something on the lighter side (chicken salad sandwiches, chicken pot pie, quiche, etc.) plus every decadent dessert you can imagine. 

We stuck to Route 66 leaving Rolla and headed towards Springfield. The bit of the drive around Devil’s Elbow is probably the prettiest in Missouri. 

We stopped in Lebanon to see the Munger Moss Motel (such a great sign!) and a few other spots there and then it was a pretty scenic drive back to Springfield where we hopped back on I-44 and headed home to Tulsa. 

Springfield, MO to Joplin, MO

February 2022

I did this bit as a day trip from Tulsa. I drove I-44 all the way to Springfield, and got off onto Route 66 around Halltown. 

Going west from Halltown, take a right when the route forks and you’ll drive past one of my favorite Route 66 sites in Missouri…Gary’s Gay Parita Sinclair Station. It hasn’t been open since the owner died, but his family is talking about maybe keeping it running. Regardless, you can pull over and see a lot from the fence. It’s a great place. 

The stretch of road from Springfield to Carthage is one of my favorites so far. It’s often called the “ghost road” because so much of it has been abandoned, but it’s really something to see. 

I stopped in Avilla at Lottie’s Soda Shoppe and it’s a good spot for a snack, drink, or quick lunch if you like what they’re fixing that day. 

Carthage is a place worth spending some time (really more so than Joplin I think). Coming into town I detoured out to see Red Fork II, which is kind of a replica of an old town. It’s out in the middle of nowhere and you can drive through the whole thing in your car. It was super muddy and pretty chilly when I was there so I didn’t get out to look around much, but it’s definitely worth the detour. 

In town, they were working on renovating the historic Boots Court hotel and I can’t wait to go back to check it out when it’s finished. 

I parked in the town square (the courthouse here is incredible) and had lunch at the newly opened Pie Safe. It was okay (chicken salad sandwiches, quiche, etc.) but I think next time I’d try the Carthage Deli for more standard diner food. 

I spent quite a bit of time going to all of the antique shops around the square and there are some GOOD ones. If you love antiques, vintage shops, etc then you’ll definitely want to carve out some time in Carthage. So far it’s one of the best bigger “small towns” I’ve come across on Route 66. 

Star Lanes looked pretty cool and in season it would be fun to catch a movie at the 66 Drive-In. 

You’ll pass through Carterville (mostly old used car lots) and Webb City (looked like some good restaurants downtown) before coming to Joplin. 

I’d read about the restoration of the Wilder’s Restaurant neon sign so I knew I wanted to see that. It’s pretty impressive and I’d definitely like to go back for dinner sometime. The Route 66 Mural Park downtown was a lot smaller than I expected, but if you’re in the area check it out. And that was honestly kind of it for me in Joplin. 


November 2021

I did all 11 miles of Route 66 through Kansas as a day trip from Tulsa ; ) I took I-44 to the Baxter Springs exit and worked my way west. Galena is the first town you’ll come to and it’s “famous” for the Cars on Route displays. 

Their claim to fame is being home to a rusty tow truck that inspired the Pixar Cars character Tow Mater and they’ve recreated half a dozen or so different cars from the movie (complete with eyes in the windshields) at different spots in town. 

There are two refurbished gas stations in town and overall the town just has a really great worn patina (in the best way). 

The old Riverton Store is a MUST STOP in Kansas. It’s the perfect little old fashioned Route 66 general store, lunch spot, souvenir shop and it’s been there since the 1920s. 

I detoured a bit to see the Rainbow Bridge, but it’s worth it. You can still drive across it. 

Downtown Baxter Springs is very historic and well preserved. The Route 66 visitor’s center is in a renovated gas station and there are several really good antique stores downtown. I stopped for a milkshake at the Monarch Pharmacy & Soda Fountain and would definitely recommend it. 

I drove all the way back to Tulsa on Route 66 since there were some parts of Miami and Vinita that I had missed on a previous trip. 

Tulsa, OK to Oklahoma City, OKC

October 2021

Since my previous trip westward in Oklahoma had been mostly interstate, I did Route 66 from Tulsa to Oklahoma City that day and saw what there was to see in Oklahoma City. The route from Tulsa to OKC is continuous and it’s a really nice drive. I stopped in Stroud and Chandler and checked out the Geodescent Dome, Milk Bottle Building, and Winchester Drive In in OKC. 

Tulsa, OK to Elk City, OK

August 2020

We did this stretch as a daytrip from Tulsa and while we did drive some portions of Route 66, it was more of a getting on and off the interstate to see specific attractions kind of trip. We drove all the way to Elk City on I-44 and worked our way back. We stopped at the National Route 66 Museum in Elk City and the Oklahoma Route 66 Museum in Clinton. After a quick stop in Hydro to see the historic Lucille’s Service Station, we cruised past OKC to Arcadia where we checked out the Round Barn and had dinner at Pops. 

Commerce, OK to Tulsa, OK 

August 2020

This was the trip that started it all! After being pretty cooped up all spring and summer with the COVID lockdowns, we decided to venture out not too far from home to hit some Route 66 stops. We took I-44 all the way to Miami and made our first stop in Commerce. The Dairy King is a MUST STOP on Route 66. It’s a historic service station converted to a little burger and ice cream stand and it couldn’t be cuter and the people couldn’t be friendlier. Across the street is a good photo opp at another service station. 

We had lunch in Miami at Waylan’s Kuku Burger and it was soooo good. Only the drive thru was open when we were there (still COVID times), but there are some picnic tables in the shade. 

We stopped at the Totem Pole Park in Foyil, which has long been on my Oklahoma bucket list and is a pretty perfect roadside attraction. 

And we wrapped up the day with a stop at the Blue Whale in Catoosa which is pretty close to home. 

Planning a Route 66 road trip? I’ve got all of the info you need! 

I’ve broken down each segment driving westbound so you know exactly what to expect: Chicago IL to St. Louis MO, St. Louis MO to Springfield MO, Springfield MO to Tulsa OK, Tulsa OK to Oklahoma City OK, Oklahoma City OK to Amarillo TX, Amarillo TX to Albuquerque NM

Plus I’ve rounded up my absolute favorite experiences (things to do, where to eat, where to stay, etc.) by state here: Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico

And I’ve got more in-depth posts on certain cities: Chicago, St. Louis, Tulsa, Amarillo, Tucumcari, and Albuquerque.