History
Entrepreneur and Oklahoman Cyrus Avery is credited with kicking off the creation of Route 66, in the hopes of creating a highway that would link Chicago and Los Angeles. Signed into law in 1927, Route 66 was one of the first original US highways, though it wasn’t completely paved until 1938.
Also in 1927 was the establishment of Avery’s U.S. Highway 66 Association which had the goals of completing paving for the road as well as promoting travel. The first publicity attempt came through the “Bunion Derby,” which had runners trek from Los Angeles to New York City by foot, using Route 66 as the main path. Many famous figures greeted the contestants as they reached certain marks, with the race finally ending in Madison Square Garden. Later, when it came time for the 1932 Summer Olympics in Los Angeles, the association put out an ad encouraging Americans to use Route 66 to get there.
In addition to the publicity that successfully sparked interest in hundreds of Americans, traffic on Route 66 increased merely because of its geography. It became a popular path for trucks and most importantly, with the 1930s Dust Bowl migration, many farmers and their families headed west for better jobs in the untouched land of southern California. New traffic aided the small towns that came to serve as rest stops and with more traffic also came the increase in businesses catering to travellers, such as motor service shops, restaurants, motels, and mom-and-pop businesses.
When World War II came around, even more people headed west on Route 66, as there were many wartime industries that needed labour in California. When the war ended and up until the 1950s, Route 66 became a popular road trip for Americans, newly optimistic in the post-war boom. During this time, Route 66 as we now know it began to take shape, and roadside tourist attractions were developed everywhere as hundreds of people used the route as a relaxing and fun road trip.
Unfortunately, when the late 1950s arrived, President Dwight D. Eisenhower signed the Interstate Highway Act which created more efficient highways to major destinations while also causing Route 66’s slow but steady decline.
Today, there has been a revival in interest in Route 66. A number of the stops on the route have been designated as national historic sites and many people now take the journey as a means to appreciate the history of the United States while getting a glimpse into the past and future of towns that once thrived during the route’s golden years.
Preparation
Time: The ideal amount of time to spend is two weeks. Any shorter and you’ll rush through many of the sites. However, if you can’t allow for two weeks, your best bet is to speed through some of the Midwest and spend more time in Texas, New Mexico, and California. If your schedule allows, you could even spend a whole month on the route! The number of random stops and turns is endless and it’s easy to want to wander, but two weeks should be enough time to see the majority of sites.
Transportation: Most people travel in cars, though some who seek adrenaline and adventure will opt for travelling by motorbike. Many rental shops will allow you to pick up a car from Chicago and drop it off in Los Angeles; expect to pay around $800 total for a two week trip. The same goes for those of you who want to rent motorbikes; prices for those go for around $750 a week.
Ideal Time: Weather-wise, April, May, and September tend to be the best times to travel, though many music festivals and big events take place during the summer.
Mapping out your Journey: It’s good to invest in a Route 66 map for your journey. The main route will take you from Illinois, through Missouri, Kansas, Oklahoma, Texas, New Mexico, and Arizona, ending in California. Many online maps will plot out the historic Route 66 path, which many people opt to take. Otherwise, you can create your own path, where you can drive along certain Route 66 roads while taking advantage of some newer highways on the way.
Check out this website to help you map out your trip in detail.
Accommodation:
And remember, when travelling Route 66, keep an open mind! At some point in time, you’ll come across junctions with Route 66 signs heading in multiple directions, which one you choose will be your decision and in many cases, you’ll end up in towns and at sights that weren’t on your list. However, that’s where much of the fun comes from and those unexpected stops will undoubtedly add to your journey.
Though everyone’s specific course might be different, there are certain sights and attractions you won’t want to miss. We’ll take you state by state and point out what each one has to offer along Route 66.
Illinois
Begin off your journey in Grant Park, the official start of Route 66. This park also famously held the 1893 World’s Fair, where a few notable products made their debut, some of which included Pabst Blue Ribbon Beer and Juicy Fruit gum. You’ll want to check out the Charles F. Buckingham Memorial Fountain, built in 1927 soon after the opening of Route 66. Try and visit at night and you’ll be treated to a fantastic light show that takes place on the hour and lasts twenty minutes. Chicago is also home to Frank Lloyd Wright’s Home and Studio, where visitors can get an authentic look into the first twenty years of the architect’s career.
As you head out of Chicago and down Route 66, make sure to stop at Funks Grove Pure Maple Sirup, a popular stop that serves up sweet and buttery homemade “sirup.”
American history, a visit to the Lincoln Home National Historic Site is a must. You can tour his perfectly preserved property for free and knowledgeable guides offer lots of information that make the entire experience worthwhile. If you find yourself hungry, you can stop over at the historic Cozy Dog Drive In, which claims to have served the very first corn dog and is a popular stop for travellers on Route 66. Eventually, you’ll reach Springfield, the capital of Illinois and the home of President Abraham Lincoln. If you’re a fan of him or just interested in some
Head back on the road and you’ll come across your first roadside attractions, including Our Lady of the Highways, a shrine of the Blessed Virgin known for watching over weary travellers on the Mother Road. A number of other historic Route 66 stops also line the road to Missouri, including the Ariston Cafe and the Soulsby Service Station. If you’re in the mood for some retro entertainment, check out Skyview Drive In, a 1950s theatre that’ll give you the authentic drive in experience.
Missouri
The first major city you’ll hit when you enter Missouri is St. Louis, the capital of the state and a city with numerous attractions. You can first visit the Chain of Rocks Bridge, which used to be a part of the historic Route 66 but has since been shut down. However, you can still walk the bridge, which offers beautiful views and an interesting 22-degree bend, but be careful of your belongings as the area is known for car break-ins.
While in St. Louis, you might as well check out the tremendous Gateway Arch and the famous cultural district of the Delmar Loop. Before leaving St. Louis, you must try the famous Ted Drewes Frozen Custard, a favourite among both travellers and locals.
The next part of your journey includes a number of famous Route 66 stops. Visit the intricate Black Madonna Shrine, which was built by a Polish monk in the early 1900s and is a replica of the National Shrine of Our Lady in Czestochowa.
Set out some time to stretch your feet out and explore the Meramec Caverns, famous for being used as Jesse James’ hideout. If you feel like you haven’t seen any kitsch in a while, don’t you worry, the fascinating World’s Largest Rocking Chair will greet you as you pass through the city of Cuba. You can also check out Devil’s Elbow Inn and Bar, a popular biker bar known for welcoming Route 66 travellers with warm hospitality. There’s also the strangely honored tradition of hanging one’s brassiere up in the bar, your choice as to whether that’s a good idea or not. After, you’ll pass through Lebanon, home to a Route 66 Museum and the landmark Munger Moss Motel, which gives you a taste of what Route 66 was like during its peak.
If you’re into quirky but meaningful art installations, you can’t leave Missouri withing spending some time at Red Oak II, a full scale 1930s town that’s perfect for great photos. You might even be lucky enough to run into the owner, Lowell Davis, who can give you the full story behind Red Oak.
Oklahoma
On your way to Oklahoma, you’ll drive through Kansas for just about 13 miles; this part of the road makes up less than 1% of Route 66 so you’ll only find a few historic stops, some of which include the Marsh Rainbow Arch Bridge and Baxter Springs.
Once you hit Oklahoma, the first sight you’ll want to see is the Route 66 Vintage Iron Motorcycle Museum. After that, drive over to Clanton’s Cafe and enjoy their famous Chicken Fried Steak. If you’re a fan of late entertainer Will Rogers, stop by the Will Rogers Memorial Museum and enjoy exploring the extensive artefacts, photos, and manuscripts from his life. Continue down the road and you’ll come across a famous Route 66 treasure, Blue Whale of Catoosa, which is a must for photos.
Eventually you’ll reach Oklahoma City, which offers up a number of attractions. First, check out the Arcadia Round Barn; the tour guides are knowledgeable and it’s a necessary stop on Route 66. Close to that is POPS, a newer and much more modern roadside attraction, which boasts over 400 different flavours of soda. If you’re in the mood for some more history, spend some time in the National Cowboy & Western Heritage Museum, highly rated for its extensive old
Western art and exhibits. You’ll also want to spend some time wandering around the Stockyards City District to get a taste of real ranch culture.
In between leaving the capital and entering Texas, make a stop at the well-organized Oklahoma Route 66 Museum, which has a restored Valentine diner and tons of Route 66 memorabilia.
Texas
The Route 66 path through Texas takes you all the way across the state’s panhandle. The first city you’ll come across is Shamrock, home to the popular U-Drop Inn, an unusual art deco service station and restaurant that was also featured in the Pixar movie Cars. Stop by the Devil’s Rope Museum as you drive toward Amarillo. It’s a cool little museum dedicated to barbed wire and its importance during settlement of the West. When you get back on the road, look out for the famous 19-story cross in Groom and the Slug Bug Ranch, a random display of VW Beetles planted in the ground.
In Amarillo, rest at the Golden Light Cafe & Cantina, a greasy spoon with a lot of Route 66 history. Otherwise, save your appetite for the Big Texan Steak Ranch, famous for its contest that consists of winning a free 72 oz steak (provided you finish it in an hour along with some side dishes…as a heads up, 5 out of every 6 people fail). Also, if you liked the Slug Bug Ranch, you’ll want to check out its 
predecessor, the Cadillac Ranch. If you do, make sure to bring some cans of spray paint and follow in the tradition of decorating the half-buried cars.
Finally, head back on the road and don’t miss the Midpoint Cafe, the famous halfway marker between Chicago and Los Angeles.
New Mexico
The next three states offer many Route 66 stops as well as many scenic outdoor stops to enjoy. Drive into New Mexico and you’ll find yourself in Tucumari. Visit the Mesaland’s Dinosaur Museum and the Tee Pee Curios shop for friendly conversations and eccentric souvenirs. You can’t leave before visiting or staying at the Blue Swallow Motel for a step back in time. It’s an absolute must if you’re even remotely interested in the historic Route 66 stops.
Next, in the city of Santa Rosa, spend some time at the Route 66 Auto Museum and enjoy the collection of usual vintage cars. If the weather’s hot and you fancy a swim, take a break and visit the Blue Hole, an 82 feet deep pool of flowing clear spring water.
If you’ve got some extra time, make a detour to the state’s capital, Santa Fe. Visit the St. Francis Cathedral for beautiful architecture and stained glass windows. For food, grab some Southwestern cuisine at Cafe Pasqual’s. Walk around the Santa Fe Plaza and if you’re there early in the morning, you’ll be treated to a market filled with Native American handicrafts. A visit to El Rancho de las Golondrinas, a “living museum,” gives visitors a firsthand look into how people lived in the Spanish colonial era. If you need a place to stay, spend the night at La Fonda on the Plaza, a charming hotel that stays true to the Santa Fe Pueblo style.
Next you’ll arrive in Albuquerque. Watch a show at the KiMo Theatre and explore the downtown area, which runs right along Route 66. Take a scenic trip along the Sandia Peak Tramway and enjoy North America’s longest aerial tram. If you happen to be visiting in early October, look out for the nine day Balloon fiesta, the largest hot air balloon festival in the world.
When you get back on the road, make sure to look out for Acoma Pueblo, also known as “Sky City.” It’s one of the oldest Native American pueblos that is still thriving today and if you don’t have time to explore the entirety of the expansive and stunning city, at least make a stop at the Cultural Center to learn about the eye-opening and fascinating history of the Acoma people.
As you head out of New Mexico, you can spend some time hiking around the El Malpais National Monument and the El Morro National Monument for ancient ruins and fascinating rock formations.
Arizona
It’s easy to spend days exploring all of the natural beauty Arizona has to offer; the state is also home to the longest stretch of Route 66. On your way through Arizona, you’ll pass by the Petrified Forest National Park, known for its huge deposits of petrified wood and colourful badlands. It’s a good place to stop for cool photos and viewpoints.
Head into Hoolbrook and visit the kid-friendly Rainbow Rock Shop for some photos with giant dinosaur statues. Another must on the historic Route 66 path is the famous Wigwam Motel, where guests spend the night in huge metal teepees (if you can’t spend the night here, don’t fret, there’s another one in San Bernadino, California). You’ve also got to try Joe and Aggie’s Cafe for cheap but delicious Tex-Mex food. After that, continue down and look out for the famous Jackrabbit Trading Post.
You’ll also pass by the famous Meteor Crater near Winslow, which has been around for over 50,000 years. Check it out for some interesting interactive exhibits and observation decks. Nearby is the Painted Desert, a huge stretch of badlands that contains gigantic rock formations with unique strips of colour. Kachina Point in the desert offers a great place for viewing and photos and if you visit close to sunset, the colours of the desert are even more beautiful.
After you’re done there, drive on to Flagstaff and visit the Wupatki National Monument and explore the ancient pueblo ruins. After, check out the Lowell Observatory, famous for its discovery of Pluto in 1930. If you’re still craving even more natural wonder and you have a few free days, a trip to the Grand Canyon is necessary. While you’re there, check out Havasu Falls for some gorgeous scenery.
Delgadillo’s Snow Cap Drive-In is the next place you can’t miss. Another historic Route 66 stop, the drive-in has a great, classic atmosphere to it and visiting it is a whole experience you won’t forget. If you can, spend some time talking to Angel Delgadillo, a Route 66 historian and brother of Juan Delgadillo, the man who founded the drive-in. Known as the “Guardian Angel of the Mother Road,” Angels owns a Route 66 gift stop not far from the drive-in and has a strong passion for protecting and promoting the stories and memories of Route 66.
Finally, make one last stop in Oatman before heading out of Arizona. It’s an original Wild West ghost town turned tourist attraction where things like gunfight re-enactments and sidewalk egg frying contests take place. If you’re there around sunrise, keep a lookout for the wild burros that descend every morning from the mountains to mooch off of tourists.
California
California, the land of possibility, is your last stop on Route 66. The number of sights to see is endless so choose wisely! As soon as you hit California, you’ll be in the Mojave Desert. Eventually you’ll reach Calico Ghost Town, where you can explore the remnants of a real mining town. Then be sure to make a quick stop at Elmer’s Bottle Tree Ranch for a bit of interesting and quirky bottle art.
Enter Upland and find the Madonna of the Trail, one of twelve monuments dedicated to women pioneers. Enjoy unique California plants at the Rancho Santa Ana Botanic Garden and then stop and enjoy The Hat’s world famous pastrami. After that, grab some dessert at The Donut Man and fall in love with their tiger tails and strawberry filled glazed donuts.
There are a number of stops you can make from here, including the Mojave Desert Heritage & Cultural Association and the famous Stone Hotel. You can also visit the very first McDonalds in San Bernadino, which houses a museum as well as the fast food. While you’re in the area, enjoy some time at the Screaming Chicken, a biker bar with a great selection of beer.
California is known for its Spanish missions and Route 66 will take you right past the San Gabriel Mission. It’s worth a stop if you’ve never been to one before. Drive on and make some time for Griffith Park, which houses its famous observatory. Hike up to the top of the observatory and you’ll get an amazing view of Los Angeles and you’ll even be able to see the famous Hollywood sign.
Drive down into Hollywood and you’ll be bombarded with sights to see and tourist traps galore. Enjoy some time just strolling around Hollywood Boulevard and walk along the Walk of Fame to find out where your favourite actors and actresses have been commemorated. After you’re done there, check out a show at the legendary El Capitan Theatre or Arclight Cinemas. If you’ve worked up an appetite, grab an old-fashioned burger and a side of onion rings at Irv’s Burgers.
End your journey in the beautiful city of Santa Monica. Make a trip to the Santa Monica Pier and ride its 1920s carousel. For some quirky and eccentric sights and people, you can’t miss Venice Beach. Finally, drive into Palisades Park, locate the Will Rogers Highway plaque which marks the official end of Route 66, and congratulate yourself!
