Traveling Route 66 in 10 Days
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As an author, I believe traveling is an incredible source of inspiration for stories, poetry, and other creative writing, so I couldn’t pass up the opportunity to travel Route 66 in ten days when I was given the chance…
Route 66 in the United States runs 2,448 miles (3,939 km) from Chicago, Illinois to Santa Monica, California. It’s a journey that’s been “paved by pioneers, risk-takers, disruptors, poets, rule-breakers, and adventurers” since 1926. I like to consider myself one of those rule-breakers since I started at the end of the route and made my way to its beginning in Chicago—which is why this guide might seem backward, but it’s great if you’re starting in California like I did.
You could drive down Route 66 for a month and still have things left over to do by the time you’re done. There’s so much to see on The Mother Road, but this guide focuses on the major sights along the way to include National Parks, landmarks, and fun local restaurants. If your time is very limited while traveling this route, then buckle up and let me help you plan your trip!
Day 1: Santa Monica Pier in California
The Santa Monica Pier was opened in 1909 and is considered to be the end of the trail. However, for the sake of this guide, this will be your starting point on Day 1. Enjoy the breeze and the Pacific Ocean view as you walk to the end of the pier, but don’t miss out on your opportunity to take a picture of the famous “End of the Trail” sign along the way. You can spend a few hours here dining, shopping, or riding the Ferris wheel at Pacific Park.
Before you leave…
At the very end of the Santa Monica Pier, you will find The Last Stop Shop. It’s literally the last store on Route 66. In this case though, it will be the first. After you hit the store, check out the cool board right outside the shop. It’s a tribute to Robert Waldmire, an American artist and cartographer who was well known for his artwork of U.S. Route 66.
Once we get going on the road again, get ready because it’s going to be about a 6 to 6.5 hour drive (+1 extra hour if you’re including the time zone change). Next stop is Seligman, Arizona.
Day 1 (Continued): Seligman, Arizona
Hopefully you made it just in time to grab some dinner at the Roadkill Café! Now, don’t be intimidated by its name. The food there is absolutely delicious, and the staff was super welcoming. One of the ladies in charge asked my friend and me why we had stopped there, and we told her we were driving Route 66 and had just started that day. She instantly got excited for us and gave us some free postcards from the restaurant. Super nice! Also, locals and tourists love their buffalo burgers. I decided to try the elk though. Was not disappointed!
Seligman is small, but…
Seligman, Arizona is basically a one-street town, but it’s well known along Route 66 largely in part to the efforts of local business owner, Angel Delgadillo, who founded the Historic Route 66 Association of Arizona in 1987. If you’re able to find him out in town, I’m sure he can tell you plenty of stories about Route 66. Unfortunately, my friend and I weren’t so lucky, mostly because we weren’t in town for long.
There’s a series of gift shops you can visit in Seligman with quirky displays out front, like a truck resembling Tow Mater from Cars. Make sure to snap all the pictures necessary!
You’ll probably want to spend the night in Seligman, Arizona for some rest. It’s a pretty small town, but there are several motels to choose from. Also, you don’t want to miss the opportunity of grabbing some ridiculously delicious breakfast at Westside Lilo’s the next day before leaving the town. Their servings were pretty huge, especially for the low price!
Day 2: Grand Canyon Caverns
After you get your huge breakfast at Westside Lilo’s, get ready to make a worthwhile detour. We’re heading to the Grand Canyon Caverns in Peach Springs, Arizona next. However, I’d like to take a moment to remind you to enjoy the ride and admire the emptiness of a long Arizona road. Route 66 is all about the journey in between, not just the beginning and the end. So, take in all the views, and cherish every moment along the way. It will be about a thirty minute drive from Seligman. Enjoy it. Isn’t it nice to not have to worry about traffic every once in a while?
Also, make sure you follow the mile markers once this long stretch ends so you don’t get lost on the way there!
Once you arrive…
The Grand Canyon Caverns off Route 66 are the largest dry caverns in the United States and range 200-300 feet (61-91 m) deep. When you arrive, your tour will begin by taking an elevator all the way down to the caverns where your guide will fill you in on all the interesting facts about the place. I’ll only share a few so I don’t spoil your trip!
The caverns were utilized as a bomb shelter in the past, and you can still find some of the old supplies and rations that were left in storage down there. However, now the Grand Canyon Caverns are an attraction where the local guides offer regular tours, Ghost Tours, and even a chance to stay at their “Cavern Suite” located 22 stories underground. Spooky. Would you spend the night between 65 million year old walls?
Boo!
Did I forget to mention that Ghost Adventures filmed one of their episodes at the Grand Canyon Caverns? Well, I hope it doesn’t make you have second thoughts about your trip here. The only ghost I met was pretty friendly. Don’t forget to ask your tour guide to turn the lights off in the cave so you can see how dark it gets down there!
By the time you arrive to the Grand Canyon Caverns and finish your tour, you might not be extremely hungry, but you might be thinking about what’s coming for lunch (if you’re anything like me). No worries! From the Peach Springs, Arizona, we’ll be heading to Williams, Arizona where you will get to visit the World Famous Sultana Bar. The lunch there was fantastic!
Day 2 (Continued): The World Famous Sultana Bar
After about an hour drive from the Grand Canyon Caverns, you will have arrived in Williams, Arizona! This mountainside town sitting at 6,780 feet (2,067 m) was originally settled by sheepherders in 1874. The town is in the heart of the Kaibab Forest and used to be a hub for ranching, lumber, and railroad workers. With them came saloons, opium dens, and gambling parlors. Life is much less crazy there now, but that brings us right into our next stop.
You must be hungry by now…
Before we get started on a few facts about the Sultana Bar, I absolutely recommend the Carnivore Nachos. Now, go have some lunch (and a drink) while you read!
The Sultana Bar is housed in an early 19th century building and claims to have the longest-operating liquor license in the state of Arizona. It operated as a speakeasy during Prohibition, and supposedly has a trapdoor that leads to underground tunnels that housed an opium den and were used by bootleggers and outlaws in the past. Crazy. What are your thoughts? Are those nachos good?
Before you leave Williams, Arizona, take your time and go visit some of the shops along its long stretch of road. Not too far from the Sultana Bar, you’ll find a big “Williams, Arizona Route 66” mural painted on the side of one of the buildings. Don’t miss out on the photo opportunity! Then whenever you’re ready, pack up and get ready for one of the most iconic stops of your trip: The Grand Canyon.
Day 2 (Continued): The Grand Canyon
This will forever be one of my absolute favorite stops out of all my trips. After about another hour of driving, you will reach the Grand Canyon’s South Rim. Pictures don’t do the Grand Canyon and its immensity any justice, so this is a stop you cannot miss. You have to see it for yourself.
Did you know The Grand Canyon National Park is 277 miles (445 km) long, 18 miles (29 km) wide, and 1 mile (1.6 km) deep?
In 1540, when Spanish explorer Garcia Lopez de Cardenas gazed at almost 2 billion years of geology from the South Rim of the Grand Canyon, he was not impressed with the view. He considered the area a desert wasteland and was more concerned about finding a way to cross it. He and his 12 companions spent three days looking for a passage to the Colorado River below with no success. Hopi guides convinced the party to turn around, but some historians believe that the Hopis knew exactly how to access the river and were actually protecting this sacred area.
My question is, how could that man not be impressed by this wonder?
Whenever you’re ready to say goodbye to the amazing views, get ready to head to Flagstaff, Arizona and get some rest for the night. The fastest route will probably be for you to head south all the way to Williams again and then taking the I-40 East. However, if you’re willing to add a few minutes to your drive, I recommend taking US-180 at the Grand Canyon Junction to Flagstaff for a beautiful and breathtaking scenic route through some of Arizona’s forest. It will be about a 1.5 hour drive.
Also, if you’re not planning on staying at hotels every night, I recommend stopping at the Little America Travel Center in Flagstaff for the night. They have food, Wi-Fi, and really clean showers available for travelers. Route 66 is full of travel stops like these, so keep an eye out for them if you’re willing to sacrifice a hotel bed for more cash in your wallet.
Day 3: Sunset Crater Volcano National Monument
About 900 years ago, a volcano erupted north of Flagstaff and reshaped the entire surrounding landscape. The 34-mile (55-km) scenic loop through Sunset Crater Volcano National Monument passes the scene of the eruption and offers views of an enormous volcanic cinder cone. It’s the most recent in a 6-million-year history of volcanic activity in the Flagstaff area. This cinder cone reminds us of the powerful forces that shape the Earth—forces that have created more than 600 hills and mountains in the San Francisco volcanic field!
What is now a 1,000-foot (304-m) high volcano began to form when molten rock sprayed high into the air from a crack in the ground, solidified, then fell to Earth as large bombs or smaller cinders. As periodic eruptions continued, the heavier debris accumulated around the vent. The lightest, smallest particles were carried the farthest by wind, dusting 800 square miles (1,287-sq-km) of northern Arizona with ash.
If you want to see the crater…
If you’re limited on time during your trip, then you might not be able to get the best view of Sunset Crater. To get the best view, you’ll have to hike the 9.6-mile (15.4-km) O'Leary Peak Trail within the park. Don’t be discouraged though! You can still do a driving tour of the Sunset Crater Volcano National Monument and Wupatki National Monument in about two hours or less.
The same processes that created Sunset Crater also created a sculpture garden of extraordinary forms at its base, which you can appreciate along the 1-mile (1.6-km) Lava Flow Trail located just a few minutes down the road from the park’s Visitor Center.
Once you’ve enjoyed the views at Sunset Crater Volcano, then you can either head straight to your next destination or (if you’re like me and like bookstores) you can head back to Flagstaff and visit Bookmans Entertainment Exchange. My favorite part about road-tripping is visiting used book stores. Reasons why? One: Books are typically in extremely good condition or practically new but still sold way cheaper at these stores. Two: Many used bookstores are pretty old and have some history behind them. Three: You’re usually supporting a local business when you choose to buy books at these stores. However, if this isn’t your thing, then get ready for your next stop: Meteor Crater.
Day 3 (Continued): Meteor Crater Natural Landmark
Yes, I know. It seems like we’re just spending the day looking at big holes in the ground. But this one is worth it. Trust me. Less than an hour drive from Flagstaff, you will reach the famous Meteor Crater Natural Landmark in Winslow, Arizona.
Picture this: 50,000 years ago, a meteor weighing several hundred thousand tons traveled through space for 500 million years before crashing into Earth at 26,000 miles per hour (41,840 kph). Hard to believe? See for yourself the 550-foot-deep (168-m) hole it left at Meteor Crater. It’s the best-preserved meteorite impact site on the planet.
Also, don’t miss out on the on-site museum! It has interactive exhibits, a fascinating history of meteorite activity on Earth, and a film theater.
I hope you enjoyed Arizona! Once you’re done at Meteor Crater, pack up and get ready for a long drive. We’re heading to New Mexico!
Day 3 (Continued): Historic Route 66 Neon Drive Thru Sign
After a 3 to 3.5 hour drive from Meteor Crater, you’ll reach Grants, New Mexico where you can park your vehicle under the famous Route 66 Neon Drive Thru. It’s a quick stop here, but you don’t want to miss the photo opportunity! Pull your car through the 18-foot-tall (5.5-m) arch shaped like a Route 66 sign—colorful by day and illuminated by night— and snap all the pictures you like.
Once you’re done, we’re heading to Albuquerque and getting some rest for the night. It’ll be another 1 to 1.5 hour drive, so if you’re hungry when you arrive, I recommend getting dinner at the 66 Diner. The food there was delicious! Also, don’t forget to look up in the restaurant and see the rows of PEZ dispensers used as decorations.
Day 4: Albuquerque Historic Old Town
The Old Town has been the heart of Albuquerque, New Mexico since the city was founded in 1706. Today, it’s the city's cultural center, with numerous museums and more than 100 shops, galleries and restaurants. After getting some breakfast, spend a few hours exploring the area and go buy some souvenirs.
Unfortunately, when I visited, some of the museums were closed or had restricted openings due to COVID-19, so I wasn’t able to do everything planned for the trip. I hope it’s different and safer for you though whenever you stop by! However, I did get the chance to pass by a group of older gentlemen gathering in the square to play some music, and it reminded me that even in the midst of chaos sometimes, life is about enjoying the simple things.
Finally, if you’re like me then you’re probably looking for those small bookstores. Head over to the slightly hidden Treasure House bookstore by the Old Town square and support the local business!
Unless anything else catches your eye in Albuquerque, get ready because you’re about to complete a 4 to 5 hour drive to Amarillo, Texas. Say goodbye to the Historic Old Town and say hello to some of the best food you’ll on your trip at the famous Big Texan Steak Ranch.
Day 4 (Continued): The Big Texan Steak Ranch
Yes, everything is bigger ‘n Texas, especially in Amarillo, Texas. I hope you worked up an appetite on your drive because you’re in store for some delicious food at this famous restaurant along Route 66. One reason why it’s so famous is because of its FREE 72oz steak dinner. Yes, I said FREE. There is a catch though…
The free 72oz steak dinner legend was born in 1960 on Route 66 (not long after founder R.J. “Bob” Lee opened The Big Texan Steak Ranch). History has it that a table full of hungry cowboys competed for Big Texan bragging rights by eating 1-pound steaks over a 1-hour period of time.
When the hour ended, 1 cowboy had eaten four and a half 1-pound steaks (total of 72oz), shrimp cocktail salad, baked potato, and bread. Lee grinned and vowed from that day forward the dinner would be free to anyone who could eat it in 1 hour. Can you do it?
Day 4 (Continued): Cadillac Ranch
Art doesn’t always have to live in a museum. Sometimes it exists in the middle of nowhere along the interstate. That’s Cadillac Ranch. In a Texas wheat field 10 miles (16.1 km) west of Amarillo (not far from The Big Texan), you’ll find 10 tail-finned, graffiti-soaked Cadillacs, manufactured between 1948 and 1964, each planted nose first in the soil.
Over the past several decades, the cars have become defaced with layers of spray paint to the point that they barely resemble Cadillacs anymore.
Hudson Marquez, one of the artists who designed and built Cadillac Ranch, said he wishes the site was more protected and that people wouldn’t litter and spray paint the cars. So, for this one, although other Route 66 guides may encourage to continue this tradition, it’s probably a better idea to maintain the site clean and safe for other travelers. Leave the spray paint at home.
Once you’re done snapping all your pictures at Cadillac Ranch, we’re getting some more driving in before the day is over and heading to Oklahoma City. When you arrive, you can enjoy the night life at Bricktown, or you can get some well deserved rest for the upcoming day.
Day 5: Breakfast at the Classen Grill
Either you decided to rest in Amarillo for the night, or you made the trip to Oklahoma City. Regardless, I bet you’re hungry and ready for breakfast! Hopefully you did make it to Oklahoma City because I must absolutely recommend grabbing some food at the Classen Grill in the morning. It’s a relatively small restaurant, but it only adds to its cozy environment and friendly service. The menu is super cheap, but the portions were enormous! This is always a plus if you’re a big eater like me.
Day 5 (Continued): The Centennial Land Run Monument
Once you’re fueled up after breakfast, head over to Bricktown. Up next, the Centennial Land Run Monument comprises 36 life-size sculptures (artist Paul Moore) that reenact the Land Rush. More sculptures are being added each year, and when completed, it will be one of the largest freestanding bronze sculptures in the world. The artwork captures the intense energy of the event in impressive detail, but it should not be overlooked that the moment in history the monument depicts is one that ripped away land from tribal members, forever changing their lives.
The monument is located in the South End of Bricktown Canal and follows a quiet walk along the flora and water. If you’re a photographer, you can easily spend an hour or two snapping a million pictures here and exploring Bricktown further. There are several bars and restaurants along the way too, but once lunch or dinner time starts coming around, I actually recommend making a drive over to Pops for an experience.
Day 5 (Continued): Pops
You’ll be impressed by the carbonated sugar drink offerings at this relatively new place in Arcadia, Oklahoma. Since this soda utopia opened in 2007, it’s become a favorite spot on Route 66. Pops has to be the most unique gas station in America. A colossal 66-foot-tall (20-m), LED-lit sculpture of a bottle emerges over the horizon on the roadside, inviting travelers to stop at the neo-futuristic service station designed by Rand Elliot. Inside, the walls shoot overhead at a sharp angle, and colorful bottles of soda line the windows in perfect succession. Also a diner, Pops serves breakfast all day, as well as burgers and shakes. It’s usually crowded here, so plan for a wait and arrive before you’re extremely hungry. There’s a gift shop inside too so be prepared to buy some souvenirs!
Once you’re done here, take the rest of the evening to rest or to enjoy the nightlife in Bricktown. There will be plenty of driving tomorrow.
Day 6: Hard Rock in Tulsa
“Isaac Tigrett and Peter Morton were two shaggy-haired Americans who just wanted to find a good American burger while living in London. Their solution? They opened up their own American style diner in an old Rolls Royce dealership in 1971. They called it Hard Rock Cafe. Today, Hard Rock International is one of the most globally recognized companies in the world and has venues in over 74 countries.”
Hopefully you’re well-rested and full from breakfast. The trip today starts with about a 2 hour drive to Tulsa where you will arrive at the Hard Rock Hotel & Casino. This may be an optional stop for you, but if you’re like me, then you like collecting souvenirs. I collect patches for my backpack, and my friend (who helped me finish this trip with me) collects the Hard Rock Hurricane Glasses, so we had to make the stop! Also, the Route 66 design at the casino’s entrance is worth making a quick stop for some pictures. It’s along the way anyways, so why not!
Day 6 (Continued): Cars on the Route
Are you a Pixar fan? If not, this is still a memorable and pretty famous stop along Route 66 that you shouldn’t miss. About another 1.5 to 2 hour drive from Tulsa, you’ll arrive in Galena, Kansas where you will find some friendly characters parked outside an old service station.
Meet the 1951 International boom truck that inspired Tow Mater, the lovable character from Pixar’s Cars. In addition to the 1950s boom truck, a replica decorated to look exactly like Tow Mater—with eyes and buck teeth—is parked next to it. For trademark reasons, the replica is named Tow Tater.
From the plaque…
Right by “Tow Tater” you’ll find a plaque with some background on the inspiration for Tow Mater. In all honesty, it not only captures the essence of the character, but also of Route 66 itself, the friendly people you meet along the way, and the generous American spirit that still lives on in small towns across the country. The plaque says the following:
“In Galena, Kansas, we found a lonely old tow truck that most folks would pass by without a second glance. Our Head of Story, Joe Ranft, however, saw the inspiration for the character Mater. They soon became kindred spirits. Joe gave Mater his warmth, his sense of fun, his humble and generous spirit, and his capacity to see and bring out the best in others.”
If you’ve taken the chance to speak with the locals along the way so far, you may have experienced some warm interactions that may be uncommon in “big city life.” It’s one of the things I’ve enjoyed most about the trip so far.
Day 6 (Continued): Whole Hog
Café
So we’ve gone from California to Arizona to New Mexico to Texas to Oklahoma to Kansas, and now… Springfield, Missouri. About another 1.5 hour drive away from Cars on the Route, you’ll find the perfect way to start a new experience in another state: some amazing food at the Whole Hog Café.
The Whole Hog Café is one of Springfield’s best barbecue spots. The Hog has won awards for their dry-rubbed meat, and they have six house-made sauces— all of which are delicious. Do not miss this stop for lunch or dinner! And come hungry, as plates such as pulled pork, burnt ends, and beef brisket come with two hearty sides and a dinner roll. It was some of the best food my friend and I had on the whole trip.
We arrived later in the evening, so once we finished eating here, we decided to get some rest for the night. However, if you’ve been extra speedy with your driving (safely I hope), go explore Springfield some more before the day is done!
Day 7: Fantastic Caverns
Y’all thought I was done with caves on this trip! I recommend starting the day off by getting some breakfast at George’s Family Restaurant. Right after, get ready for another interesting underground tour.
Located about 5 miles (8 km) north of Springfield, Missouri, Fantastic Caverns offers a jeep-drawn tram that takes visitors on a ride into the cave. You’ll see fluted draped stalactites, stalagmites, and flowstones all beautiful and creepy in their otherworldliness.
The true creepy thing about this cave though is that the Ku Klux Klan once conducted secret meetings and cross burnings in the cave in the 1920s. The tour guides have much to teach about these natural formations and their history. And if you’re lucky, they’ll point out to you a formation that looks like, what they call, the “Scooby Doo Monster.” Don’t miss this stop when traveling through Missouri on Route 66!
Day 7 (Continued): The World’s Largest Fork
Before heading here, you can also check out Bookmarx in town if you’re into used book stores. It was one of my favorites on the trip! If not, then get ready for some enormous eating utensils right after Fantastic Caverns.
The World’s Largest Fork almost 5 miles (8 km) south of downtown Springfield, Missouri is, well... pretty self explanatory. The fork stands 35 feet (11 m) tall and weighs 11 tons (10 metric tons). Colorado also claims to have the world’s largest fork, but regardless, this is one of those odd Route 66 attractions worth stopping for—take a picture.
Imagine the kind of dinner you’re having if you’re using a fork that big...
Day 7 (Continued): Larry Baggett’s Trail of Tears Memorial
Unfortunately, all my pictures from this site got deleted somehow, but my buddy managed to save me by sending me this picture he had snapped on his phone.
After about a 1.5 hour drive from The World’s Largest Fork in Springfield, you’ll arrive at Larry Baggett’s Trail of Tears Memorial in Jerome, Missouri. Once you arrive, make sure to park on the side of the road! Even though it looks like a driveway, this memorial is a walking trail.
Segments of Route 66 from Rolla to Springfield follow the 1838 Trail of Tears. This was the northern route onto which U.S. troops forced tens of thousands of Cherokee, Creek, Seminole, Chickasaw, and Choctaw to walk 1,200 miles (1,931 km) across the country to reservations in Oklahoma. At least 4,000 died from disease, exposure, and starvation.
When my friend and I arrived at the memorial, the site was technically closed, but the very kind and warm older lady who is now restoring the site invited us in and gave us a tour of the place. We told her we were traveling Route 66, and she was excited to have visitors and share the history of the place.
Years ago, a past resident of Jerome, Missouri—Larry Baggett— was repeatedly awakened by a loud knocking at his door. But when he answered it, no one was there. Later, an old Cherokee man visited him, saying that Baggett’s house was built on the Trail of Tears and that many Cherokee had camped near his home. The knocking was from the spirits who were still trying to walk the trail, but Baggett’s house was blocking their path. Baggett decided to build a set of stairs on a stone wall on his property to help the spirits cross. Suddenly, the knocking ceased. Soon after, he built a stone archway, as well as concrete and stone sculptures on his property, to memorialize American Indians and honor their struggle. Baggett died in 2003, and even though much of the Trails of Tears Memorial is now in ruins, it’s in the process of being restored.
As we left the site, the lady who gave us the tour, and who also shared she was part Native American, kept repeating to us, “Infinite Blessings to you.” Again, just another example of the kind and interesting people you meet along The Mother Road.
Day 7 (Continued): The Red Rocker
After the Trail of Tears Memorial, you’re only about a thirty minute drive from your next “World’s Largest.”
It might be silly to say “keep an eye out for” the World’s Largest Rocking Chair on Route 66—at 42 feet (13 m) tall and 20 feet (6 m) wide, you won’t miss it. The gigantic rocker is made of steel pipe, and although it once held the crown of “World’s Largest Rocking Chair,” in 2015 a 56.5-foot-tall (17.2-m) chair was erected in Illinois. Hence, the Fanning, Missouri chair’s current title.
The chair used to rock, but the owner worried that this monstrosity could tip over and kill someone, so now the rockers are welded at the base. Make a stop here and take a picture with another one of Route 66’s odd attractions.
Day 7 (Continued): Fitz’s Restaurant
Ever had a craft soda? Well, from The Red Rocker, you’ll be a 1.5 hour drive away from St. Louis, Missouri where you will end your day with some amazing dinner. You can’t miss the fizzy goodness on tap at Fitz’s, where more than a dozen flavors range from sassafras root to vanilla bean.
Today, Fitz’s sits in the heart of the Delmar Loop, a ten-block section of distinctive stores, shops, and even a renovated movie theater dating back to the 1930s. Grab a burger and a float, and then if you’re up for it, explore a bit of that Delmar Loop.
Also, if you’re in the mood, don’t forget to ask the servers about their “boozy” options at the restaurant.
Day 8: Gateway Arch National Park
Did you know the iconic “Gateway to the West” (Gateway Arch National Park) is the tallest constructed monument in the United States? Yep. Completed in 1965, the 630-foot (192-m) stainless steel monument points westward, symbolizing the path to prosperity, opportunity, and freedom. That’s double the size of the Statue of Liberty which stands at 305 feet (93 m). However, it’s still not as tall as the Empire State Building in New York which stands at 1250 feet (381 m) or Chicago’s Sears Tower at 1454 feet (443 m). This will be the first stop on Day 8 of your trip.
You’ll start the day off at this national park and can spend an hour or two here if you decide to explore the museum located beneath the Arch! Afterwards, you can do a bit of walking and explore the downtown area until you reach the grand Union Station. When it opened in 1894, it was reportedly the largest, most beautiful train station in the United States—and today it still maintains its regal elegance. An additional option after visiting the Gateway Arch is taking a tour at the Anheuser-Busch Brewery. Unfortunately, when I visited, the brewery was still closed due to COVID-19. Hopefully you have better luck though (if you’re into drinking) whenever you plan your visit to St. Louis!
Day 8 (Continued): The Cozy Dog Drive-In
About a 1.5 to 2 hour drive from downtown St. Louis, you’ll find the Cozy Dog Drive-In, where you’ll stop for some lunch or dinner. The restaurant lies south of Springfield, Illinois, after Route 66 merges with 6th Street. Ed and Virginia Waldmire (parents of Route 66 artist Bob Waldmire—remember him from Day 1?!) opened the Cozy Dog in 1949. It’s still run by the Waldmire family, and the place is packed with souvenirs, drawings, and Route 66 memorabilia. The drive-in is located on a busy highway, but it’s hard to miss. Just keep an eye out for a huge yellow sign with two giant hot dogs in a sweet embrace.
Day 9: Abraham Lincoln Presidential Museum
Today will be slightly different from the rest of the trip since we’ll spend most of it learning about a U.S. President, specifically, good ol’ Abe and the different stages of his life in Springfield, Illinois along Route 66. President Abraham Lincoln practiced law here from 1843 to about 1852, and is buried at the city’s Oak Ridge Cemetery. The Abraham Lincoln Presidential Library & Museum is one of the most popular presidential libraries. It’s a 200,000-square-foot (18,581-sq-m) complex with 40,000 square feet (3,716 sq m) of galleries, theater presentations, historical artifacts, and interactive exhibits.
The Lincoln Home National Historic Site—only a short walk from the museum—is the two-story Greek Revival home that Lincoln lived in from 1844 to 1861. Built in 1839, the property has been restored to look as it did when Lincoln lived there, and several pieces of furniture on display are originals.
Day 9 (Continued): Oak Ridge Cemetery
Finally, Lincoln’s resting place is north of downtown at the Oak Ridge Cemetery, the second-most popular cemetery in America after Arlington National Cemetery in Washington DC. After he was assassinated, his body was eventually interred here in 1874. His three youngest sons and Mrs. Lincoln are also buried here.
You may want to drive here after finishing your visits at the museum and the home site, since the cemetery is not within walking distance! Also, it was pretty chilly when I visited Springfield!
Once we finish in Springfield, it’s time to head to the last city on our trip: Chicago. However, it’s about a 3 hour drive so I recommend stopping for food first. Along the way in Bloomington is the Lucca Grill. Route 66 road-trippers have been eating there since 1936, and everyone agrees that Lucca’s has the best thin-crust pizza in the area. An antique tin ceiling and vintage bar give the place some old-school charm and serve as a reminder that the restaurant has been around for a while.
Day 9 (Continued): Dell Rhea's Chicken Basket
After arriving in Chicago, my buddy and I checked in to our hotel, got some rest, visited the Hard Rock Café in the city, and then made the best possible choice for dinner.
One of the best places to eat on Route 66 is Dell Rhea's Chicken Basket. The neon sign is legendary—very hard to miss—and the fried chicken is amazing. But the Chicken Basket didn’t always serve chicken. Initially, it operated as a simple lunch counter. In the late 1930s, two farm women offered to sell the owner their farm’s eggs, including their recipe for fried chicken. Locals and travelers have been worshipping the succulent crispy fried chicken and fried mac-and-cheese balls ever since. Don’t miss out on this one during your trip along Route 66!
Day 10: Field Museum of Natural History
The Field Museum of Natural History in Chicago may be one of the few attractions known as much for what’s not on display as for what is. The museum’s library holds 250,000 volumes on the history of the earth and upward of 20 million curios from around the world, each catalogued and set aside for study when not out on display. Like that of many Chicago museums and landmarks, the Field Museum’s inception coincided with the 1893 World’s Columbian Exposition.
In 2000, the museum garnered international attention when it debuted Sue, the largest, most complete, and best preserved Tyrannosaurus rex fossil ever discovered. Several other permanent exhibits exploring Africa and Asia trace the culture and environment of those continents with life-size dioramas. the museum regularly unveils new items and collections, and special events bring regular visitors back for another helping.
Day 10 (Continued): Millennium Park and Cloud Gate
Within walking distance from the Field Museum and the Buckingham Fountain, Millennium Park is a green-space oasis in the middle of a bustling metropolis. In it, you’ll find Cloud Gate. Sculpted by Mumbai’s Anish Kapoor, it looks like a giant polished-chrome… jellybean? But that description doesn’t do it justice. The sculpture was blocked off due to COVID-19 reasons, however the curves of the distinctive art piece reflect the sky and, typically, the groups of people gathered around it.
The images are distorted in surprisingly beautiful ways as you pass by the gate. It’s one of the city’s most popular photo ops, and one you certainly do not want to miss.
Day 10 (Continued): Begin Route 66 Sign
It’s been quite the adventure, but it has finally come to its end. Or is it the beginning? As a reminder, we’ve been traveling Route 66 backwards, so this is actually where the route would begin if you started in Illinois.
The specific starting point for Route 66 has moved several times. The 1926 alignment was at Jackson Boulevard and Michigan Avenue, near the Art Institute of Chicago. In 1933, the start of Route 66 moved a couple of blocks east to Jackson Boulevard and Lake shore Drive, near the World’s Fair. Then, in 1955, Jackson became a one way street heading eastbound; Adams Street, one block north, became the new westbound starting point for Route 66. Across the street from the Art Institute at Michigan Avenue and Adams, you can spot the historic “Begin Route 66” sign.
So what do you say? Let’s give it another go, this time from Chicago to Santa Monica? Let’s refuel first though. Go to Lou Malnati's Pizzeria for some legendary Chicago Deep Dish Pizza.
Route 66 is blessed by its rich history, the stories shared by its people along the way, and the expectation of every traveler to rediscover themselves on the open road. I experienced ten days of oddities and charm that shed a warm light upon places I never knew were a part of America. I slept in a car with my best friend, was uncomfortable at times, and ripped a few socks from so much walking on the trip, but being able to travel with so much freedom was a transformative experience I will always appreciate. I hope many others get to experience a trip like this in life, and it’s the biggest reason why I’ve prepared this guide. I wish I had more time and infinite funds in order to experience Route 66 more fully, but ten days was still enough time to experience so many new things and create new memories.
However, if you by chance have more time than I did, I have to recommend getting yourself a copy of Jessica Dunham’s Moon Route 66 Road Trip (Travel Guide). I would not have been able to plan as detailed of a trip as I did without that guide, and most of the information I provide here is derived from her work. She provides hundreds of additional experiences and sites along Route 66, so if you have more time or are planning on redoing the road trip at some point, her guide is absolutely essential. And if you’re looking for a decent camera to capture all your memories, I recommend the one I use: the Canon EOS REBEL SL3.
Anyways, thank you for reading this far. I wish you safe travels and I hope you create memories for a lifetime.
Moon Route 66 Road Trip (Travel Guide) by Jessica Dunham
Moon Route 66 Road Trip reveals the ins and outs of this iconic highway, from sweeping prairies and retro roadside pit-stops to the stunning vistas of the Southwest. Inside you'll find:
Maps and Driving Tools: 38 easy-to-use maps detail the existing roads that comprise the original Route 66, along with site-to-site mileage, driving times, detailed directions for the entire route, and full-color photos throughout
Eat, Sleep, Stop and Explore: With lists of the best hikes, bites, roadside curiosities, and more, you can admire extraordinary landscapes like Acoma Pueblo or Joshua Tree National Park, explore big cities like Los Angeles and Chicago, or wander abandoned ghost towns. Immerse yourself in classic Americana with outsider art and kitsch masterpieces, find the most Instagram-worthy retro motels, and sample the breadth of regional cuisine, from deep-dish pizza to carne asada
Flexible Itineraries: Moon Route 66 Road Trip covers Illinois, Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona, and California. Drive the entire original Mother Road in two weeks, or follow strategic routes for shorter trips to Chicago, Los Angeles, St. Louis, Santa Fe, and the Grand Canyon, plus side trips to Taos, Las Vegas, Joshua Tree, and Santa Monica
Expert Perspective: Jessica Dunham has driven thousands of miles along the famed highway and provides cultural insight, insider tips, and critical history of the route
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