
Route 66 is synonymous with road trip and what better way to hit the road than with two besties in a 1973 VW bus? With LuLu being ever closer to hitting the road, I wanted to start seriously thinking about the first long trip I’ll be taking in her. I think the most logical (and most fun) option would be to travel the historic Route 66 and take it all in on America’s Mother Road!
Because I live in Colorado, I think the best way to make this work will be to actually start the route in Chicago, IL where Route 66 actually starts (or ends). Driving LuLu out that way just to come back when I’m already halfway through the route doesn’t make a ton of sense to me, though. I think, instead, I’ll plan to fly to Chicago. I’ll rent a car from there until a rendezvous point where I can make the switch to LuLu. So, without further ado, lets highlight what that trip might look like!
Route 66 starts in Chicago, Illinois and to travel the path today, you’ll take Interstate Highway 55 (I-55) to where it meets up with I-44 in Missouri. The route then meets up with I-40 and heads due west in Oklahoma on to California where it ends in Santa Monica. In total, Route 66 connected 7 states and skirted just around the lower border of Nevada. According to the National Parks Service, Historic Route 66 now includes 250 historic sites. Those sites encompass buildings, roadways, and bridges.
Illinois

To set off our journey, the first stop is the last stop on Route 66 – Grant Park, Chicago, IL. This park has remained since the heyday of the Mother Road. From there, a stop at Lou Mitchell’s to get some food is in order. This restaurant has been kept very similar to how it was in the 1950’s. From the floor to the tradition of handing out donut holes and Milk Duds to patrons in line, not much has changed.
We’ll be starting our journey off strong, because in addition to some grub and a cool bridge, there’s also our first “roadside attraction”. The Gemini Giant is located in Wilmington, IL and is 30 feet tall. He’s a cool green guy wearing a space helmet and holding a rocket, named after the Gemini Space program. He’s one of many, many “Muffler Men” statues featured along the roadway.
After getting a meal in our tummies and enjoying some kitschy roadside America, its time to set off – on foot. The next spot is no longer a space that can be travelled by car, but is thankfully open to pedestrian and bike travel. This would be the Chain of Rocks Bridge connecting Madison, IL and St. Louis, MO. The bridge is interesting in its own right – it has a 30 degree angle partway through – but has also remained largely unchanged since its decommission in 1968.
Missouri

Once we leave Illinois and enter into Missouri, the first place I’d like to stop is the Gateway Arch is St. Louis. This arch really does have a long history of being a starting point to the West.
Then, after a long day of exploring and travel, it’ll be time to tuck into bed. There’s no better way to do that than in a neon sign-ladened motor court that’s been in operation since the inception of Route 66. That would be the Wagon Wheel Hotel, Cafe, and Station in Cuba, MO.
Missouri also holds the world’s second largest rocking chair as a feature of Route 66. That title used to fall to one in Colorado (which I’ve seen) but has been surpassed by this one, Red Rocker, in Fanning, MO (also surpassed by one elsewhere).

Before leaving Missouri, we’ll have to make time to catch a movie at the 66 Drive-in movie theater. This is one of the few operational drive-ins along the original Route 66, still using and displaying its original structures. Drive-ins used to be very common and if you’ve never been, I highly recommend finding one!
Kansas

After a good nights sleep in Missouri, the route takes us into Kansas, but only briefly. Make sure not to blink!
Near Baxter Springs, you can still drive over the last remaining example of a Marsh Rainbow Arch Bridge along historic Route 66. The Brush Creek Bridge is not part of the general thoroughfare but it has been restored such that you can still drive across it. Keep in mind, its a bridge that goes over Brush Creek. If you search “Brush Creek Bridge” it will take you to an entirely different location not in Baxter Springs.
Next up, to stock up on snacks and grab some souvenirs will be a stop at Williams’ Store (now Eisler Brother’s Old Riverton Store). It’s glass-enclosed porch is still present along with the tin-clad ceiling. It’s now a market, general store, and deli featuring the original deli counter in the back!
Oklahoma

Once Route 66 makes it through Kansas, it starts going due west in Oklahoma and travels across the entire state. We’ll encounter our second roadside attraction here – the Blue Whale of Catoosa. This construction was a later addition to the area, being finished in 1972. This creation is 20 feet tall, 80 feet long, and located next to a small pond.
Another bridge, Bridge #18, is a great example of a steel truss bridge of the era. Personally, I enjoy the architecture of a good old bridge. This is a bridge you can no longer drive over, but something worth admiring nonetheless. It’s located near Sapulpa, OK which is just as historic.
Next up in Oklahoma, it’ll be time to get some grub at Rock Cafe, which reopened in 2009. It’s lasted through decline of the Mother Road, tornados, and even a fire in 2008. Since then, its been restored and is open to current day Route 66 travelers.
With some full bellies, there are a few roadside attractions in Oklahoma that look to be worth checking out. The Arcadia Round Barn is not too far away. It truly is an architectural wonder that had people stopping to admire during the height of Route 66’s use. The barn is constructed from softened and rounded wood beams. It was also used as a central point for the community during its build.The next is in Oklahoma City.
It’s Milk Bottle Grocery and while its been a number of things since Route 66 was formally closed, the one thing that hasn’t changed is the enormous milk bottle on the roof. The second is near Hydro, OK and its Ed Galloway’s Totem Pole Park. It’s just one example of the art installations you might find along the Mother Road. Ed Galloway was a folk artist who carved, assembled, and painted several totems which still stand on the property today. He also made violins, of which can be seen in the museum that now sits at Totem Pole Park.
Carrying us further into Oklahoma is a gorgeous bridge that reminds me of days gone by – the Lake Overholser Bridge. It’s still fully functional for local traffic and really lends itself to the nostalgia of the historic Mother Road.
Our last stop, and a great place to stretch our legs, is the McLain Rogers Park. It is an Art Deco delight! It still houses many of the things originally installed for entertainment in the 1930’s and ’40s like putt-putt golf and amphitheaters along with, of course, the original neon sign.
Texas

Once in Texas, the city of Shamrock is a real architectural beauty. While it’s no longer a cafe (bummer!), the Tower Station and U-Drop Inn Cafe still looks very similar to how it did during Route 66’s golden years. It’s currently a visitor center (among other uses) but it really embodies the nostalgia of what it must have felt like to drive the road.
Amarillo is the only large city that formed around Route 66 while it coursed through the panhandle of Texas. And in Amarillo is another roadside attraction – Cadillac Ranch. This art installation is one I’ve been to, but I think its worth a stop. Next time, I think I’ll be more prepared with the offering of spray paint I bring with me.
New Mexico

After leaving the Texas Panhandle, we head into a long drive through New Mexico. Once here, you can see the architecture really take a change from Midwestern Art Deco and Mid-Century Modern. Buildings start to take on a wholly Southwestern look through the use of Spanish Revival and Mexican architecture. Leaning into the Southwestern atmosphere is Maisel’s Trading Post. It opened after completion in 1939 and has been selling curios and souvenirs ever since, even employing over 300 Native American craftsmen. With its glowing sign, it also has the kitschy vibe that I love, making visiting an absolute must!
Another bedtime stop that is cute as a button is the Blue Swallow Inn. It’s still operational today and the trademark neon of the Mother Road has been restored to its former glory. It’s neon swallow sits proudly out front, beckoning to a time before the interstate took the place of Route 66.

The Santo Domingo Trading Post is another renovated historic site along Route 66. Its located within the bounds of the Santo Domingo Pueblo and is currently closed to the public. Pictures are okay (of the building only). It operated all the way until 1995, when the owner passed away. It was supported by the residents of the Pueblo as a gas station and a place to buy food and small groceries, even after Route 66 was rerouted. The facade of the building has been restored, still including the slogan “Most Interesting Spot in the Old West…where real Indians trade”. Renovations are ongoing.
Nothing says Route 66 like neon signage and Hotel El Rancho has plenty! Headed west out of New Mexico, you’ll find this hotel in Gallup, NM. It hosted actors, crews, and other movie personnel during Hollywood’s Golden Age, making it historic in more than one way.
Arizona

New Mexico has many historic places along the original Route 66, and so does Arizona. More bridges, places to stay, and historic districts lead us through the state. First up is the Painted Desert Inn, which is located within Petrified Forest National Park, making it a two-for-one stop! It’s been restored and is now a museum after re-opening in 2006. You can see its rich culture and beautiful architectural design, along with artifacts from the area.
The next stop feels iconic – Wigwam Motel #6. Teepees made of concrete surround a main office depicting the residence of the chief and his family. Each of the teepees is decorated with a red zigzag pattern. Present day, the main office is a museum. It houses the original owners own collection of Route 66 memorabilia.

One very prominent, historic district on the itinerary is in none other than that of Seligman, AZ. Due to successful lobbying in the 1980’s, the town started promoting Seligman as the “Birthplace of Route 66”. In this area, you can see buildings and business around the original Route 66, as well as around the more direct re-routed road. You can really see the how much of a mark the automobile made along Route 66 here, with multiple dealerships, gas stations, and garages. Then, of course, there’s the theater and pool hall, and all that to say – this is a historic district worth checking out!
As we head out of Arizona, there’s one final stop that interests me for multiple reasons. The entirety of Route 66 is historic, but some place are historic for other reasons than simply that they were birthed by the roads creation. Some places are historic for both! One such place is the Durlin Hotel (now known as the Oatman Hotel) in the city of Oatman, AZ. Originally a flourishing business under the mining boom in the area, it then found a place among travelers of Route 66 once mining operations were closed. Not only that, Clark Gable and Carole Lombard stopped at the hotel during their honeymoon. And, the icing on the cake…its also purportedly haunted! The haunts include rumored guests Clark and Carole along with poltergeist activity.
California

Eight states and many miles later, we’ve reached the end of the Mother Road: California! First, we’ll revisit an old flame – Wigwam Village #7. You didn’t think those numbers were for nothing, did you? Wigwam Village #7 was the last Wigwam to be built. It’s also one of three remaining Wigwam Villages and one of two on Route 66. It’s these motels that were featured in the movie Cars as the “Cozy Cone Motel.”
Our final roadside stop is a fixture known as Elmer’s Bottle Tree Ranch. Elmer passed a few years ago, but his family has taken over caring for the display and trinkets. They seem to have a real connection to Route 66 and the Mojave desert that they strive to bring to others.
And thus, we’ll end our trip on the Santa Monica Pier. Just like in Chicago, you’ll find an “End of Trail” sign here, making a great last photo-op. The end of the most epic of road trips!

Route 66 is a long stretch of road and I couldn’t possibly cover everything there is to see along the way. There’s many, many more abandoned places that have their own nostalgia around them that I didn’t include. There’s also many more historic sites along the route, but these are the ones that really piqued my interest. Hopefully, I’ll be able to hit the road sooner rather than later, but until then…

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