Route 66, and its 2,500 miles, is known affectionately as "The Mother Road." It's the quintessential cross-country road trip experience. From Chicago through the beating heart of America and down to Los Angeles, the route officially ends at the Santa Monica Pier. The road reached peak popularity in the late 40's and early 50's before being officially removed from the US Highway System in 1985. After a few years, travelers from America and beyond started feeling tinges of nostalgia, and by the end of the 1980's it was fast becoming one of the most popular road trip routes once more.
The Illinois stretch of Route 66 is home to some pretty good eats, especially if you like classic American cuisine. Before you hit the road, visit Dell Rhea's Chicken Basket, just outside Chicago, for some of the best fried chicken you'll ever have. They've been serving the home-cooked goodness since 1946.
For those of you with a sweet tooth, Funks Grove Pure Maple Sirup in Shirley, IL produces over 1,800 gallons of maple syrup using old-fashioned techniques, and it's all bottled in beautiful, vintage-looking bottles.
The Illinois stretch of Route 66 is also home to loads of great roadside attractions, but none shout "retro-kitsch" louder than the massive muffler men statues! The Gemini Giant in Wilmington and Bunyon With a Hotdog in Atlanta, IL are two of the best for photo-ops of this iconic vestige of Americana. While you're in Atlanta, which is a ridiculously charming little town in Illinois, visit the Route 66 Arcade Museum: it's a fantastic hidden gem that features tons of vintage arcade machines you can play.
Illinois is also great for history buffs, as it's home to loads of Abraham Lincoln-inspired attractions, and since the establishment of Route 66, big 'ole statues of "Honest Abe" have been delighting road travelers over the years. For the full Lincoln experience, spend the night at the Pasfield House Inn in Springfield, and just down the road there's the Watermelon Lincoln Monument, and the Railsplitter Covered Wagon in Lincoln.
If quirky roadside attractions are your thing, then you can't get much better than Henry's Rabbit Ranch in Staunton, where you'll find a whole bunch of VW Rabbits all cut in half and sticking out of the ground, like some weird Stonehenge homage. There's also a gift shop and info center on site, and a few actual bunnies that hang around to meet travelers. It's such a sweet stop to make along the route and has so much to photograph, including massive vintage Route 66 signs and memorabilia.
As you drive through Missouri, there's a couple must-eat places once you hit St. Louis, including the classic 60-year old Eat-Rite Diner, which is like stepping back in time. Afterwards, polish off your meal with dessert at another Route 66 icon, Ted Drewes Frozen Custard.
While in St. Louis, stretch your legs with a visit to the Laumeier Sculpture Park & Museum. Here you can get a great picture of a gigantic, massive, eyeball in the middle of a field. It's pretty wild and fun to walk around the outdoor art exhibits.
Next up: Kansas! The Kansas section of Route 66 isn't what you'd call "lengthy", by any means. In fact, it's just 14 miles, but it's absolutely worth a visit. If you're coming in from Joplin, MO heading west, your first stop should be Galena, at the restored Kan-O-Tex service station now called "Cars on the Route". There are little snacks and sandwiches for sale, as well as antiques and Route 66 memorabilia. As part of their vision to connect visitors with the town, many of the items for sale are made by local craftspeople and artists. And what Route 66 service station would be complete without an old truck made to look like “Tow Mater,” from the Disney/Pixar film Cars?
When you're hungry, head to Clanton's Cafe in Vinita, OK. This retro Route 66 restaurant is best-known for its breakfast, local cuisine, which includes their world-famous chicken fried steak and calf fries.
The historic Rock Cafe in Stroud is another iconic Route 66 stop. It also has a deep connection to the movie "Cars" and it was also featured on the show "Diners, Drive-Ins, and Dives." It's famous for its mouthwateringly golden-brown chicken-fried steak, and if you're in the mood for something sweet, try their Diet Doctor Pepper float.
Oklahoma also has its share of retro Route 66 hotels (notable today for their vintage signage). A few of the more famous ones along the route are the Desert Hills Motel in Tulsa, the Skyliner Motel in Stroud, and the Lincoln Motel in Chandler.
After all that driving, you're probably thirsty. Head over to POPS Soda Ranch in Arcadia. This is a landmark gas station and diner, but the real draw here is the hundreds of sodas they offer. Plus, there's a massive 66-ft tall soda bottle out front for a great photo-op.
Also, get a photo in front of Lucille's Famous Rt. 66 Gas Station in Hydro, OK. This historic two-story gas station was built by Carl Ditmore in 1929 in a very rural area... in fact the area is still very rural, but there's a nearby stream where locals go to find fossils and arrowheads.
If you've had your fill of chicken-fried steak, and are in the mood for some good barbecue, head to Jiggs Smoke House in Clinton. It's a Route 66 road food icon, and one of the most famous BBQ joints on the Mother Road.
On to Texas! The Lone Star state still has about 150 miles of Route 66 road still remaining, and it all closely parallels Interstate 40, so it's easy to hop on and off the patches of Mother Road. A few highlights include Shamrock, Texas, which is home to the Conoco Tower. This once-bustling stop along the route remains a great place to take pictures to this day. Of all the gas stations, open or closed, in America, this may be one of the most stunning. It’s just a hop, skip, and jump off I-40, so you really have no excuse not to stop and see this roadside classic. While you’re in Shamrock, also hit up their very own Blarney Stone.
Another great little Texas town to visit is McLean. Here you can stop at the Phillips 66 on the Route, a vintage 1928 gas service station that was designed in what was known as "Cottage Fashion," because it resembled a little country cottage. Adorable!
Get your nature kicks on Route 66 at Palo Duro Canyon State Park. This is America's second largest canyon, and it only costs $5 to enter. You can easily drive the length of the park and pull over for some scenic overlooks. There's also a sizeable campground in the park.
No Route 66 trip through Texas would be complete without a big Texan-style meal. Do yourself a favor and head to The Big Texan Steak Ranch. It's a Route 66 legend with its 72oz steak challenge, which began way back in 1962. Just a couple years after owner Bob Lee opened the doors he noticed the influx of hungry cowboys on their paydays looking to down some hearty steaks. One Friday in 1962 he set up an eating contest to see who could eat the most one-pound steaks in an hour. After one cowboy downed 72oz worth of steak (along with a salad, a shrimp cocktail, and a baked potato) Lee declared that anyone who could eat that much steak in an hour gets it for free... and so a legend was born.
When you're ready for a cold beer and some good tunes, visit the Golden Light Cantina in Amarillo. It's a fantastic little roadhouse that serves up burgers and beers, and also frequently has swinging live music.
Once you reach Adrian, Texas, pat yourself on the back: you've made it to the middle of Route 66! You'll know you've arrived once you see the MidPoint Cafe, a vintage-style roadside diner, with lots of photo-ops to commemorate your journey down the Mother Road.
Best time of year to travel along Route 66: The best time to road trip down Route 66 is between late April and early July, as well as late August through late October. The worst times to visit would be July and August, this is when the temperature is sweltering and all the kids are out of school, which means you'll come across some crowds along the route. In addition, July and August is considered high season, so you're going to be paying higher rates for lodging.